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Bufotenin, also known as dimethylserotonin or as 5-hydroxy-''N'',''N''-dimethyltryptamine (5-HO-DMT), is a
serotonergic psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...
of the
tryptamine Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the firs ...
family. It is a
derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...
of the psychedelic
dimethyltryptamine Dimethyltryptamine (DMT), also known as ''N'',''N''-dimethyltryptamine (''N'',''N''-DMT), is a Psychedelic drug, serotonergic hallucinogen and Investigational New Drug, investigational drug of the substituted tryptamine, tryptamine family tha ...
(DMT) and of the
neurotransmitter A neurotransmitter is a signaling molecule secreted by a neuron to affect another cell across a Chemical synapse, synapse. The cell receiving the signal, or target cell, may be another neuron, but could also be a gland or muscle cell. Neurotra ...
serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
(5-hydroxytryptamine; 5-HT). The compound is an
alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...
found in some species of
mushroom A mushroom or toadstool is the fleshy, spore-bearing Sporocarp (fungi), fruiting body of a fungus, typically produced above ground on soil or another food source. ''Toadstool'' generally refers to a poisonous mushroom. The standard for the n ...
s,
plants Plants are the eukaryotes that form the kingdom Plantae; they are predominantly photosynthetic. This means that they obtain their energy from sunlight, using chloroplasts derived from endosymbiosis with cyanobacteria to produce sugars f ...
, and
toad Toad (also known as a hoptoad) is a common name for certain frogs, especially of the family Bufonidae, that are characterized by dry, leathery skin, short legs, and large bumps covering the parotoid glands. In popular culture (folk taxonomy ...
s. It is also found naturally in the human body in small amounts. Bufotenin, for instance derived from the trees ''
Anadenanthera colubrina ''Anadenanthera colubrina'' (also known as vilca, huilco, huilca, wilco, willka, curupay, curupau, cebil, or angico) is a South American tree closely related to yopo, or ''Anadenanthera peregrina''. It grows to tall and the trunk is very thorn ...
'' and ''
Anadenanthera peregrina ''Anadenanthera peregrina'', also known as yopo, jopo, cohoba, parica or calcium tree, is a perennial tree of the genus ''Anadenanthera'' native to the Caribbean and South America. It grows up to tall, and has a thorny bark. Its flowers grow ...
'', has a long history of
entheogen Entheogens are psychoactive substances used in spiritual and religious contexts to induce altered states of consciousness. Hallucinogens such as the psilocybin found in so-called "magic" mushrooms have been used in sacred contexts since ancie ...
ic use as a snuff in
South America South America is a continent entirely in the Western Hemisphere and mostly in the Southern Hemisphere, with a considerably smaller portion in the Northern Hemisphere. It can also be described as the southern Subregion#Americas, subregion o ...
. The name bufotenin originates from the toad genus ''
Bufo ''Bufo'' is a genus of true toads in the amphibian family Bufonidae. As traditionally defined, it was a wastebasket genus containing a large number of toads from much of the world but following taxonomic reviews most of these have been moved to ...
'', which includes several species of
psychoactive toad The Colorado River toad (''Incilius alvarius''), also known as the Sonoran Desert toad, is a toad species found in northwestern Mexico and the southwestern United States. It is well known for its ability to exude toxins from glands within its sk ...
s, most notably ''
Incilius alvarius The Colorado River toad (''Incilius alvarius''), also known as the Sonoran Desert toad, is a toad species found in northwestern Mexico and the southwestern United States. It is well known for its ability to exude toxins from glands within its sk ...
'' (formerly ''Bufo alvarius''), that
secrete Secretion is the movement of material from one point to another, such as a secreted chemical substance from a cell or gland. In contrast, excretion is the removal of certain substances or waste products from a cell or organism. The classical mec ...
bufotoxin Bufotoxins are a family of toxic steroid lactones or substituted Substituted tryptamine, tryptamines of which some are toxic. They occur in the parotoid glands, skin, and poison of many toads (True toad, Bufonidae family) and other amphibians, an ...
s from their
parotoid gland The parotoid gland (alternatively, paratoid gland) is an external skin gland on the back, neck, and shoulder of some frogs (especially toads), and salamanders. It can secrete a number of milky alkaloid substances (depending on the species) known ...
s. However, ''Bufo'' and related species like ''Incilius alvarius'' contain only trace amounts of bufotenin, with their major active component instead being
5-MeO-DMT 5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine), also known as ''O''-methylbufotenin or mebufotenin (), is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by ...
. In addition to DMT and serotonin, bufotenin is similar in
chemical structure A chemical structure of a molecule is a spatial arrangement of its atoms and their chemical bonds. Its determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target m ...
to other psychedelics such as 5-MeO-DMT and
psilocin Psilocin, also known as 4-hydroxy-''N'',''N''-dimethyltryptamine (4-HO-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocy ...
(4-HO-DMT). These compounds also occur in some of the same fungus, plant, and animal species as bufotenin. Bufotenin acts as a potent and non-selective
serotonin receptor agonist A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin (5-hydroxytryptamine; 5-HT), a neurotransmitter and hormone and the endogenous ligand of t ...
, including of the serotonin 5-HT1A, 5-HT2A, 5-HT2C, and 5-HT3 receptors, among others. It also acts as a potent and specific
serotonin releasing agent A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter ...
. The compound is more
hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are n ...
than other related tryptamines and consequently is more peripherally selective. In relation to this, bufotenin has been associated with prominent
peripheral A peripheral device, or simply peripheral, is an auxiliary hardware device that a computer uses to transfer information externally. A peripheral is a hardware component that is accessible to and controlled by a computer but is not a core compo ...
serotonergic
side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...
s, such as
cardiovascular In vertebrates, the circulatory system is a system of organs that includes the heart, blood vessels, and blood which is circulated throughout the body. It includes the cardiovascular system, or vascular system, that consists of the heart a ...
changes. The cardiovascular effects of bufotenin can be powerful and potentially dangerous. For many decades and even into the present, bufotenin has been considered by many experts, such as
David E. Nichols David Earl Nichols (born December 23, 1944, Covington, Kentucky) is an American pharmacologist and medicinal chemist. Previously the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worke ...
, to be either inactive or only weakly active as a psychedelic in humans and to produce robust
toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...
effects.
Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...
was also uncertain whether bufotenin was an active psychedelic. However,
Jonathan Ott Jonathan Ott (born 1949 in Hartford, Connecticut) is an ethnobotanist, writer, translator, publisher, natural products chemist and botanical researcher in the area of entheogens and their cultural and historical uses, and helped coin the term "' ...
found in 2001 via
self-experimentation Self-experimentation refers to single-subject research in which the experimenter conducts the experiment on themself. Usually this means that a single person is the designer, operator, subject, analyst, and user or reporter of the experiment. Al ...
that bufotenin is in fact a potent psychedelic and does not necessarily produce serious adverse effects.
Hamilton Morris Hamilton Morris (born April 14, 1987) is an American journalist, documentarian, and scientific researcher. He is the creator and director of the television series ''Hamilton's Pharmacopeia'', in which he investigated the chemistry, history, and ...
has further supported these findings with his own self-experimentation, although bufotenin was reported to be strongly nauseating for himself and many others. According to Morris, the psychedelic effects of bufotenin are like a cross between those of DMT and 5-MeO-DMT. Morris has stated that bufotenin may in fact be the psychedelic with the longest history of human entheogenic use. Bufotenin has also been encountered as a
recreational drug Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an Sub ...
in forensic samples, for instance in
New York City New York, often called New York City (NYC), is the most populous city in the United States, located at the southern tip of New York State on one of the world's largest natural harbors. The city comprises five boroughs, each coextensive w ...
.


Use and effects


Fabing & Hawkins (1955)

In 1955, Fabing and Hawkins administered bufotenin
intravenously Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutr ...
at doses of up to 16mg to prison inmates at
Ohio State Penitentiary The Ohio State Penitentiary (OSP) is a 502-inmate capacity supermax Ohio Department of Rehabilitation and Correction prison in Youngstown, Ohio, United States. Throughout the last two centuries, there have been two institutions with the n ...
. A toxic effect causing purpling of the face was seen in these tests. A subject given 1mg reported "a tight feeling in the chest" and prickling "as if he had been jabbed by needles." This was accompanied by a "fleeting sensation of pain in both thighs and a mild nausea." Another subject given 2mg reported "tightness in his throat." He had tightness in the stomach, tingling in pretibial areas, and developed a purplish hue in the face indicating blood circulation problems. He vomited after 3 minutes. Another subject given 4mg complained of "chest oppression" and that "a load is pressing down from above and my body feels heavy." The subject also reported "numbness of the entire body" and "a pleasant Martini feeling-my body is taking charge of my mind." The subject reported he saw red spots passing before his eyes and red-purple spots on the floor, and the floor seemed very close to his face. Within 2 minutes these visual effects were gone, and replaced by a yellow haze, as if he were looking through a lens filter. Fabing and Hawkins commented that bufotenin's psychedelic effects were "reminiscent of /nowiki>LSD">LSD.html" ;"title="/nowiki>LSD">/nowiki>LSD/nowiki> and mescaline but develop and disappear more quickly, indicating rapid central action and rapid degradation of the drug".


Isbell (1956)

In 1956, Harris Isbell at the
Public Health Service Hospital The Bureau of Medical Services (BMS) was a unit of the United States Public Health Service (PHS) that existed in two incarnations. The first was one of three principal operating agencies of PHS from 1943 until 1966, while the second was a divi ...
in
Lexington, Kentucky Lexington is a Consolidated city-county, consolidated city coterminous with and the county seat of Fayette County, Kentucky, United States. As of the 2020 United States census, 2020 census the city's population was 322,570, making it the List of ...
, experimented with bufotenin as a snuff made from ''
Anadenanthera peregrina ''Anadenanthera peregrina'', also known as yopo, jopo, cohoba, parica or calcium tree, is a perennial tree of the genus ''Anadenanthera'' native to the Caribbean and South America. It grows up to tall, and has a thorny bark. Its flowers grow ...
''. He reported "no subjective or objective effects were observed after spraying with as much as 40 mg bufotenine"; however, subjects who received 10–12mg by
intramuscular Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles hav ...
injection reported "elements of visual hallucinations consisting of a play of colors, lights, and patterns."


Turner & Merlis (1959)

Turner and Merlis (1959) experimented with
intravenous administration Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutr ...
of bufotenin (as the water-soluble creatinine sulfate salt) to schizophrenics at a New York state hospital. They reported that when one subject received 10mg during a 50-second interval, "the
peripheral nervous system The peripheral nervous system (PNS) is one of two components that make up the nervous system of Bilateria, bilateral animals, with the other part being the central nervous system (CNS). The PNS consists of nerves and ganglia, which lie outside t ...
effects were extreme: at 17 seconds,
flushing Flushing may refer to: Places Netherlands * Flushing, Netherlands, an English name for the city of Vlissingen, Netherlands United Kingdom * Flushing, Cornwall, a village in Cornwall, England * The Flushing, a building in Suffolk, England ...
of the face, at 22 seconds, maximal inhalation, followed by maximal
hyperventilation Hyperventilation is irregular breathing that occurs when the rate or tidal volume of breathing eliminates more carbon dioxide than the body can produce. This leads to hypocapnia, a reduced concentration of carbon dioxide dissolved in the blo ...
for about 2 minutes, during which the patient was unresponsive to stimuli; her face was plum-colored." Finally, Turner and Merlis reported: After pushing doses to the morally admissible limit without producing visuals, Turner and Merlis conservatively concluded: "We must reject bufotenine . . . as capable of producing the acute phase of
Cohoba Cohoba is a Taíno transliteration for a ceremony in which the ground seeds of the ''cojóbana'' tree (''Anadenanthera'' spp.) were used as a hallucinogenic snuff, snuff via a Y-shaped snuff tray, snuff tube. Use of this substance produced a hall ...
intoxication."


Hofmann (1963)

Albert Hofmann Albert Hofmann (11 January 1906 – 29 April 2008) was a Swiss chemist known for being the first to synthesize, ingest, and learn of the psychedelic effects of lysergic acid diethylamide (LSD). Hofmann's team also isolated, named and synthesi ...
tried bufotenin
orally The word oral may refer to: Relating to the mouth * Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid **Oral administration of medicines ** Oral examination (also known as an oral exam or oral ...
at doses of up to 50mg but experienced no psychoactive effects.


McLeod and Sitaram (1985)

A 1985 study by McLeod and Sitaram in humans reported that bufotenin administered
intranasally Nasal administration, popularly known as snorting, is a route of administration in which drugs are insufflated through the nose. It can be a form of either topical administration or systemic administration, as the drugs thus locally delivered ca ...
at a dose of 1–16mg had no effect, other than intense local irritation. When given
intravenously Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutr ...
at low doses (2–4mg), bufotenin
oxalate Oxalate (systematic IUPAC name: ethanedioate) is an anion with the chemical formula . This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (), and several esters such as ...
caused anxiety but no other effects; however, a dose of 8mg resulted in profound emotional and perceptual changes, involving extreme
anxiety Anxiety is an emotion characterised by an unpleasant state of inner wikt:turmoil, turmoil and includes feelings of dread over Anticipation, anticipated events. Anxiety is different from fear in that fear is defined as the emotional response ...
, a sense of imminent death, and visual disturbance associated with color reversal and distortion, and intense flushing of the cheeks and forehead.


Shulgin (1997)

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...
reviewed the literature on bufotenin in his book ''
TiHKAL ''TiHKAL: The Continuation'' is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to '' PiHKAL: A Chemical Love Story'', ''TiHKAL'' is an acronym that stands for "Trypt ...
''. However, he and his collaborators did not appear to try it themselves.


Ott (2001)

In 2001, ethnobotanist
Jonathan Ott Jonathan Ott (born 1949 in Hartford, Connecticut) is an ethnobotanist, writer, translator, publisher, natural products chemist and botanical researcher in the area of entheogens and their cultural and historical uses, and helped coin the term "' ...
published the results of a study in which he self-administered
free base In chemistry, a free base (freebase, free-base) is a term for the neutral form of an amine or other Lewis base. The term is used in the pharmaceutical industry in contrast to salt-based formulations like hydrochlorides. The amine is often an ...
bufotenin via
insufflation In religious and magical practice, insufflation and exsufflation are ritual acts of blowing, breathing, hissing, or puffing that signify variously expulsion or renunciation of evil or of the devil (the Evil One), or infilling or blessing with go ...
(5–100mg),
sublingually Sublingual (abbreviated SL), from the Latin for "under the tongue", refers to the pharmacological route of administration by which substances diffuse into the blood through tissues under the tongue. Many drugs are absorbed through sublingual a ...
(50mg),
rectally The rectum (: rectums or recta) is the final straight portion of the large intestine in humans and some other mammals, and the gut in others. Before expulsion through the anus or cloaca, the rectum stores the feces temporarily. The adult hu ...
(30mg),
orally The word oral may refer to: Relating to the mouth * Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid **Oral administration of medicines ** Oral examination (also known as an oral exam or oral ...
(100mg) and via
vaporization Vaporization (or vapo(u)risation) of an element or compound is a phase transition from the liquid phase to vapor. There are two types of vaporization: evaporation and boiling. Evaporation is a surface phenomenon, whereas boiling is a bulk phenome ...
(2–8mg). Ott reported "visionary effects" of intranasal bufotenin and that the "visionary threshold dose" by this route was 40mg, with smaller doses eliciting perceptibly psychoactive effects. He reported that "intranasal bufotenine is throughout quite physically relaxing; in no case was there facial rubescence, nor any discomfort nor disesteeming side effects". At 100mg, effects began within 5minutes, peaked at 35 to 40minutes, and lasted up to 90minutes. Higher doses produced effects that were described as psychedelic, such as "swirling, colored patterns typical of tryptamines, tending toward the arabesque". Free base bufotenin taken sublingually was found to be identical to intranasal use. The potency, duration, and psychedelic action was the same. Ott found vaporized free base bufotenin active from 2 to 8mg with 8mg producing "ring-like, swirling, colored patterns with eyes closed". He noted that the visual effects of insufflated bufotenin were verified by one colleague, and those of vaporized bufotenin by several volunteers. Ott concluded that free base bufotenin taken intranasally and sublingually produced effects similar to those of
Yopo ''Anadenanthera peregrina'', also known as yopo, jopo, cohoba, parica or calcium tree, is a perennial tree of the genus ''Anadenanthera'' native to the Caribbean and South America. It grows up to tall, and has a thorny bark. Its flowers grow ...
without the toxic peripheral symptoms, such as facial flushing, observed in other studies in which the drug was administered
intravenously Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutr ...
.


Morris (2020s)

Hamilton Morris Hamilton Morris (born April 14, 1987) is an American journalist, documentarian, and scientific researcher. He is the creator and director of the television series ''Hamilton's Pharmacopeia'', in which he investigated the chemistry, history, and ...
, a
psychoactive drug A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...
journalist A journalist is a person who gathers information in the form of text, audio or pictures, processes it into a newsworthy form and disseminates it to the public. This is called journalism. Roles Journalists can work in broadcast, print, advertis ...
, the creator of ''
Hamilton's Pharmacopeia ''Hamilton's Pharmacopeia'' is an American docuseries, which premiered on Viceland on October 26, 2016. The show follows Hamilton Morris as he explores the history, chemistry and social impact of psychoactive substances. It chronicles Morris' ...
'', and a
pharmacologist Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur between ...
, has experimented with bufotenin and found that it was an active psychedelic. He has claimed that its effects are like a cross between those of DMT and 5-MeO-DMT, being less visual than DMT but more visual than 5-MeO-DMT. Morris has also stated that bufotenin is very nauseating and this has made it unpleasant for himself and other people. By
insufflation In religious and magical practice, insufflation and exsufflation are ritual acts of blowing, breathing, hissing, or puffing that signify variously expulsion or renunciation of evil or of the devil (the Evil One), or infilling or blessing with go ...
, he has said that its duration is about 1hour and is longer than that of DMT or 5-MeO-DMT. Morris and others have suggested use of the
serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
5-HT3 receptor
antagonist An antagonist is a character in a story who is presented as the main enemy or rival of the protagonist and is often depicted as a villain.ondansetron Ondansetron, sold under the brand name Zofran among others, is a medication used to prevent nausea and vomiting caused by chemotherapy, radiation therapy, migraines, or surgery. It is also effective for treating gastroenteritis. It can be giv ...
(Zofran) to prevent nausea and vomiting with especially nauseating or serotonin 5-HT3 receptor agonistic serotonergic psychedelics like bufotenin.


Side effects

Side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...
s of bufotenin include
nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...
and
vomiting Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pre ...
, among others. It can also produce powerful and potentially dangerous and frightening
cardiovascular In vertebrates, the circulatory system is a system of organs that includes the heart, blood vessels, and blood which is circulated throughout the body. It includes the cardiovascular system, or vascular system, that consists of the heart a ...
side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...
s at doses that allow for hallucinogenic effects.


Overdose

The acute toxicity () of bufotenin in rodents has been estimated at 200 to 300mg/kg. Death occurs by respiratory arrest. In April 2017, a South Korean man died after consuming bufotenin-containing
toad Toad (also known as a hoptoad) is a common name for certain frogs, especially of the family Bufonidae, that are characterized by dry, leathery skin, short legs, and large bumps covering the parotoid glands. In popular culture (folk taxonomy ...
s that had been mistaken for edible Asian bullfrogs, while in Dec. 2019, five Taiwanese men became ill and one man died after eating bufotenin-containing Central Formosa toads that they mistook for frogs.


Interactions


Pharmacology


Pharmacodynamics

Bufotenin is an analogue of the
monoamine neurotransmitter Monoamine neurotransmitters are neurotransmitters and neuromodulators that contain one amino group connected to an aromatic ring by a two-carbon chain (such as -CH2-CH2-). Examples are dopamine, norepinephrine and serotonin. All monoamines ...
serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
. Similarly to serotonin and related compounds like
dimethyltryptamine Dimethyltryptamine (DMT), also known as ''N'',''N''-dimethyltryptamine (''N'',''N''-DMT), is a Psychedelic drug, serotonergic hallucinogen and Investigational New Drug, investigational drug of the substituted tryptamine, tryptamine family tha ...
(DMT), bufotenin is an
agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...
of the serotonin 5-HT1A, 5-HT2A, 5-HT2C, 5-HT3, and 5-HT4 receptors. It is also known to bind with high
affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...
to other
serotonin receptor 5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in multiple tissues including the central and peripheral nervous systems. They mediate both ex ...
s, including the serotonin 5-HT1B, 5-HT1D, 5-HT1F, 5-HT6, and 5-HT7 receptors. Bufotenin has about 5- to 10-fold higher affinity for the serotonin 5-HT2A receptor than
5-MeO-DMT 5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine), also known as ''O''-methylbufotenin or mebufotenin (), is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by ...
, about the same activational
potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of ho ...
as 5-MeO-DMT at the receptor ''
in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...
'' ( = 3.49nM and 3.87nM, respectively), and about 3-fold higher ''
in-vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, and ...
'' potency than 5-MeO-DMT when they are in the
brain The brain is an organ (biology), organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It consists of nervous tissue and is typically located in the head (cephalization), usually near organs for ...
. In contrast to many other psychedelic tryptamines, bufotenin shows high affinity for the serotonin 5-HT3 receptors, similar to or higher than that of serotonin, and this receptor is strongly associated with production of
nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...
and
vomiting Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pre ...
. In addition to its serotonin receptor agonism, bufotenin is a potent
serotonin releasing agent A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter ...
(SRA) with an value of 30.5nM, whereas it is inactive as a releaser of
dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...
or
norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...
( > 10,000nM). A special property of 5-MeO-DMT is that it has much higher affinity for and activational potency at the serotonin 5-HT1A receptor compared to other psychedelic tryptamines such as DMT and this is thought to confer it with unique and distinct hallucinogenic effects. Similarly, bufotenin has also shown greatly increased affinity for the serotonin 5-HT1A receptor. Whereas the serotonin 5-HT1A receptor affinities (Ki or ) of tryptamine and DMT were 125nM and 170nM, respectively, the affinities of serotonin (5-HO-T),
5-methoxytryptamine 5-Methoxytryptamine (5-MT, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or ''O''-methylserotonin and as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. It has been shown to oc ...
(5-MeO-T), bufotenin (5-HO-DMT), and 5-MeO-DMT were 3nM, 9nM, 4.9nM, and 6.5nM, respectively. Comparing bufotenin to DMT, it had 35-fold higher affinity for the serotonin 5-HT1A receptor in comparison. Findings were very similar in another study not only in terms of affinities but also activational potencies. Bufotenin had a similar at the serotonin 5-HT1A receptor as serotonin, 5-MeO-T, and 5-MeO-DMT (13nM, 3nM, 14nM, and 21nM, respectively), and a far greater value than tryptamine or DMT (899nM and 1,293nM, respectively). Bufotenin is thought to have reduced capacity to cross the
blood–brain barrier The blood–brain barrier (BBB) is a highly selective semipermeable membrane, semipermeable border of endothelium, endothelial cells that regulates the transfer of solutes and chemicals between the circulatory system and the central nervous system ...
due to its relatively high
hydrophilicity A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are no ...
and hence to show significant
peripheral selectivity Peripherally selective drugs have their primary mechanism of action outside of the central nervous system (CNS), usually because they are excluded from the CNS by the blood–brain barrier. By being excluded from the CNS, drugs may act on the rest o ...
. As a result, bufotenin has a greater ratio of
peripheral A peripheral device, or simply peripheral, is an auxiliary hardware device that a computer uses to transfer information externally. A peripheral is a hardware component that is accessible to and controlled by a computer but is not a core compo ...
activity to central effect. Bufotenin produces the
head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...
, a behavioral proxy of psychedelic effects, in rodents. However, it requires doses about 10-fold higher than those of psilocybin to produce behavioral responses in rats. Conversely, unlike other psychedelics, bufotenin fails to substitute for
LSD Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...
,
psilocybin Psilocybin, also known as 4-phosphoryloxy-''N'',''N''-dimethyltryptamine (4-PO-DMT), is a natural product, naturally occurring tryptamine alkaloid and Investigational New Drug, investigational drug found in more than List of psilocybin mushroom ...
, or
5-MeO-DMT 5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine), also known as ''O''-methylbufotenin or mebufotenin (), is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by ...
in rodent
drug discrimination Drug discrimination (DD) is a technique in behavioral neuroscience used to evaluate the discriminative stimulus properties or interoceptive cues of psychoactive drugs. In drug discrimination, a subject is trained on a training drug, and then i ...
tests. Relatedly, findings on the effects of bufotenin in animals have been described as "equivocal". Studies have been similarly mixed on the
psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...
effects of bufotenin in humans, with some finding a relative lack of psychedelic effects and pronounced toxic effects, while others have found psychedelic effects without major adverse effects. In any case, bufotenin has often been reported to produce pronounced peripheral
serotonergic A serotonergic substance, medication, or receptor protein is one that affects neurotransmission pathways that involve serotonin, as follows: * Serotonergic drugs ** Serotonin receptor agonists ** Serotonin receptor antagonists ** Serotonin reupta ...
effects. These have included
cardiovascular In vertebrates, the circulatory system is a system of organs that includes the heart, blood vessels, and blood which is circulated throughout the body. It includes the cardiovascular system, or vascular system, that consists of the heart a ...
,
gastrointestinal The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The tract is the largest of the body's systems, after the cardiovascular system. ...
, and other effects, among them increased
respiratory rate The respiratory rate is the rate at which breathing occurs; it is set and controlled by the respiratory center of the brain. A person's respiratory rate is usually measured in breaths per minute. Measurement The respiratory rate in humans is mea ...
, chest heaviness, purpling of the head and neck skin (intense
skin flushing Flushing is to become markedly red in the face and often other areas of the skin, from various physiological conditions. Flushing is generally distinguished from blushing, since blushing is psychosomatic, milder, generally restricted to the face ...
),
nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...
,
vomiting Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pre ...
, and
retching Retching (also known as dry heaving) is the reverse movement (retroperistalsis) of the stomach and esophagus without vomiting. It can be caused by bad smells or choking, or by withdrawal from certain medications, or after vomiting has completed. R ...
. It is possible that in addition to its limited central permeation, the peripheral effects of bufotenin have served to mask its central and hallucinogenic effects. The adverse effects of bufotenin may be more pronounced with
intravenous injection Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutr ...
compared to other routes such as
insufflation In religious and magical practice, insufflation and exsufflation are ritual acts of blowing, breathing, hissing, or puffing that signify variously expulsion or renunciation of evil or of the devil (the Evil One), or infilling or blessing with go ...
. In contrast to peripheral administration,
intracerebroventricular injection Intracerebroventricular injection (often abbreviated as ICV injection) is a route of administration for drugs via injection into the cerebral ventricles so that it reaches the cerebrospinal fluid (CSF). This route of administration is often used ...
of bufotenin in animals readily produces robust psychedelic-like behavioral effects similar to those of other serotonergic psychedelics like
5-MeO-DMT 5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine), also known as ''O''-methylbufotenin or mebufotenin (), is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by ...
. In addition, 5-MeO-DMT, the ''O''-
methylated Methylation, in the chemical sciences, is the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These term ...
analogue of bufotenin, which has greater
lipophilicity Lipophilicity (from Greek λίπος "fat" and φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are called lipophilic (translated ...
, is readily able to cross the blood–brain barrier and produce psychedelic effects. Bufotenin
prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s, with greater lipophilicity than bufotenin itself, like ''O''-acetylbufotenin and ''O''-pivalylbufotenin, have also shown robust psychedelic-like effects in animals.


Pharmacokinetics

Bufotenin has been reported to undergo a strong
first-pass effect The first pass effect (also known as first-pass metabolism or presystemic metabolism) is a phenomenon of drug metabolism at a specific location in the body which leads to a reduction in the concentration of the active drug before it reaches the ...
and to not be orally active. This is in contrast to its
positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...
psilocin Psilocin, also known as 4-hydroxy-''N'',''N''-dimethyltryptamine (4-HO-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocy ...
, which is thought to form a pseudo-ring system that limits its susceptibility to
metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...
by
monoamine oxidase Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The fi ...
(MAO). However, bufotenin actually does show oral activity if sufficiently high doses are taken. About 10-fold higher doses of bufotenin seem to be required orally compared to
parenteral In pharmacology and toxicology, a route of administration is the way by which a drug, fluid, poison, or other substance is taken into the body. Routes of administration are generally classified by the location at which the substance is applied. ...
ly for effects. In rats, subcutaneously administered bufotenin (1–100μg/kg) distributes mainly to the
lungs The lungs are the primary organs of the respiratory system in many animals, including humans. In mammals and most other tetrapods, two lungs are located near the backbone on either side of the heart. Their function in the respiratory syste ...
,
heart The heart is a muscular Organ (biology), organ found in humans and other animals. This organ pumps blood through the blood vessels. The heart and blood vessels together make the circulatory system. The pumped blood carries oxygen and nutrie ...
, and
blood Blood is a body fluid in the circulatory system of humans and other vertebrates that delivers necessary substances such as nutrients and oxygen to the cells, and transports metabolic waste products away from those same cells. Blood is com ...
, and to a much lesser extent, the
brain The brain is an organ (biology), organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It consists of nervous tissue and is typically located in the head (cephalization), usually near organs for ...
(
hypothalamus The hypothalamus (: hypothalami; ) is a small part of the vertebrate brain that contains a number of nucleus (neuroanatomy), nuclei with a variety of functions. One of the most important functions is to link the nervous system to the endocrin ...
,
brain stem The brainstem (or brain stem) is the posterior stalk-like part of the brain that connects the cerebrum with the spinal cord. In the human brain the brainstem is composed of the midbrain, the pons, and the medulla oblongata. The midbrain is co ...
,
striatum The striatum (: striata) or corpus striatum is a cluster of interconnected nuclei that make up the largest structure of the subcortical basal ganglia. The striatum is a critical component of the motor and reward systems; receives glutamat ...
, and
cerebral cortex The cerebral cortex, also known as the cerebral mantle, is the outer layer of neural tissue of the cerebrum of the brain in humans and other mammals. It is the largest site of Neuron, neural integration in the central nervous system, and plays ...
), and
liver The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...
. Only very small amounts of bufotenin reach the brain in rats following
intravenous administration Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutr ...
, which is attributed to its poor
lipophilicity Lipophilicity (from Greek λίπος "fat" and φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are called lipophilic (translated ...
and consequent
peripheral selectivity Peripherally selective drugs have their primary mechanism of action outside of the central nervous system (CNS), usually because they are excluded from the CNS by the blood–brain barrier. By being excluded from the CNS, drugs may act on the rest o ...
. The brain-to-blood ratio of
5-MeO-DMT 5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine), also known as ''O''-methylbufotenin or mebufotenin (), is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by ...
(''O''-methylbufotenin) was 15times higher than that of bufotenin in the study. Bufotenin reaches peak circulating concentrations at one hour and is nearly eliminated within 8hours. In humans,
intravenous Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutr ...
administration of bufotenin results in
excretion Excretion is elimination of metabolic waste, which is an essential process in all organisms. In vertebrates, this is primarily carried out by the lungs, Kidney (vertebrates), kidneys, and skin. This is in contrast with secretion, where the substa ...
of (70%) of injected drug in the form of 5-HIAA, an
endogenous Endogeny, in biology, refers to the property of originating or developing from within an organism, tissue, or cell. For example, ''endogenous substances'', and ''endogenous processes'' are those that originate within a living system (e.g. an ...
metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...
of serotonin, while roughly 4% is eliminated unmetabolized in the urine. Orally administered bufotenin undergoes extensive
first-pass metabolism The first pass effect (also known as first-pass metabolism or presystemic metabolism) is a phenomenon of drug metabolism at a specific location in the body which leads to a reduction in the concentration of the active drug before it reaches the ...
by the enzyme
monoamine oxidase Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The fi ...
.
Psilocin Psilocin, also known as 4-hydroxy-''N'',''N''-dimethyltryptamine (4-HO-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocy ...
(4-HO-DMT) is a
positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...
of bufotenin and might be expected to have similarly limited lipophilicity and blood–brain permeability. However, psilocin appears to form a
tricyclic Tricyclics are cyclic chemical compounds that contain three fused rings of atoms. Many compounds have a tricyclic structure, but in pharmacology, the term has traditionally been reserved to describe heterocyclic drugs. They include antidepr ...
pseudo-ring system wherein its
hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
and
amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
interact through
hydrogen bonding In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, Covalent bond, covalently b ...
. This in turn results in psilocin being much less
polar Polar may refer to: Geography * Geographical pole, either of the two points on Earth where its axis of rotation intersects its surface ** Polar climate, the climate common in polar regions ** Polar regions of Earth, locations within the polar circ ...
, more lipophilic, and more able to cross the blood–brain barrier and exert central actions than it would be otherwise. In contrast, bufotenin is not able to achieve this pseudo-ring system. Accordingly, bufotenin is less lipophilic than psilocin in terms of
partition coefficient In the physical sciences, a partition coefficient (''P'') or distribution coefficient (''D'') is the ratio of concentrations of a chemical compound, compound in a mixture of two immiscible solvents at partition equilibrium, equilibrium. This rati ...
. In any case, bufotenin does still appear to show significant central permeability and, like psilocybin, can produce robust hallucinogenic effects in humans.


Chemistry

Bufotenin, also known as 5-hydroxy-''N'',''N''-dimethyltryptamine (5-HO-DMT), is a
substituted tryptamine Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all trypt ...
and a
derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...
of
dimethyltryptamine Dimethyltryptamine (DMT), also known as ''N'',''N''-dimethyltryptamine (''N'',''N''-DMT), is a Psychedelic drug, serotonergic hallucinogen and Investigational New Drug, investigational drug of the substituted tryptamine, tryptamine family tha ...
(DMT; ''N'',''N''-dimethyltryptamine) and
serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
(5-hydroxytryptamine; 5-HT). It is also closely related to
psilocin Psilocin, also known as 4-hydroxy-''N'',''N''-dimethyltryptamine (4-HO-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocy ...
(4-HO-DMT) and
5-MeO-DMT 5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine), also known as ''O''-methylbufotenin or mebufotenin (), is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by ...
. The predicted
log P Log most often refers to: * Trunk (botany), the stem and main wooden axis of a tree, called logs when cut ** Logging, cutting down trees for logs ** Firewood, logs used for fuel ** Lumber or timber, converted from wood logs * Logarithm, in mathem ...
of bufotenin ranges from 0.89 to 2.04. For comparison, the predicted log P of DMT is 2.06 to 2.5, of serotonin is 0.2 to 0.56, of 5-MeO-DMT is 1.5 to 2.38. and of psilocin is -0.14 to 2.1.


Analogues and derivatives

Some analogues and
derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...
s of bufotenin (5-HO-DMT), aside from serotonin and DMT, include
psilocin Psilocin, also known as 4-hydroxy-''N'',''N''-dimethyltryptamine (4-HO-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocy ...
(4-HO-DMT) (a
positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...
),
6-hydroxy-DMT 6-Hydroxy-DMT, also known as 6-hydroxy-''N'',''N''-dimethyltryptamine, is a serotonin receptor modulator of the tryptamine family. "6-HO-DMT is a minor metabolite of DMT in man, and it was studied for the same reasons. Could this compound play a ...
(another positional isomer),
5-MeO-DMT 5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine), also known as ''O''-methylbufotenin or mebufotenin (), is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by ...
(''O''-methylbufotenin), ''O''-acetylbufotenine, ''O''-pivalylbufotenine,
bufotenidine Bufotenidine, also known as 5-hydroxy-''N'',''N'',''N''-trimethyltryptammonium (5-HTQ), is an indole toxin related to bufotenin, serotonin, and other tryptamines which is found in the venom of a variety of toads. It acts as a selective serotonin ...
(''N''-methylbufotenin), bufoviridine (bufotenin ''O''-sulfate), 5-HO-DiPT, and α-methylserotonin, among others.


Natural occurrence


Toads

Bufotenin is found in the skin and eggs of several species of toads belonging to the genus ''
Bufo ''Bufo'' is a genus of true toads in the amphibian family Bufonidae. As traditionally defined, it was a wastebasket genus containing a large number of toads from much of the world but following taxonomic reviews most of these have been moved to ...
'', but is most concentrated in the
Colorado River toad The Colorado River toad (''Incilius alvarius''), also known as the Sonoran Desert toad, is a toad species found in northwestern Mexico and the southwestern United States. It is well known for its ability to exude toxins from glands within its sk ...
(formerly ''Bufo alvarius'', now ''Incilius alvarius''), the only toad species with enough bufotenin for a psychoactive effect. Extracts of
toad toxin Bufotoxins are a family of toxic steroid lactones or substituted tryptamines of which some are toxic. They occur in the parotoid glands, skin, and poison of many toads (Bufonidae family) and other amphibians, and in some plants and mushrooms. The ...
, containing bufotenin and other bioactive compounds, have been used in some traditional medicines such as ''ch'an su'' (probably derived from ''
Bufo gargarizans The Asiatic toad or Chusan Island toad (''Bufo gargarizans'') is a species of toad endemic to East Asia. The species was previously classified as ''Bufo bufo gargarizans'', a subspecies of the common toad. Distribution and habitat It is commo ...
''), which has been used medicinally for centuries in China. It is also found in the
cane toad The cane toad (''Rhinella marina''), also known as the giant neotropical toad or marine toad, is a large, Terrestrial animal, terrestrial true toad native to South America, South and mainland Central America, but which has been Introduced spe ...
(''Rhinella marina''). The toad was "recurrently depicted in
Mesoamerican Mesoamerica is a historical region and cultural area that begins in the southern part of North America and extends to the Pacific coast of Central America, thus comprising the lands of central and southern Mexico, all of Belize, Guatemala, El S ...
art", which some authors have interpreted as indicating that the effects of ingesting ''Bufo'' secretions have been known in Mesoamerica for many years; however, others doubt that this art provides sufficient "ethnohistorical evidence" to support the claim. In addition to bufotenin, ''Bufo'' secretions also contain
digoxin Digoxin (better known as digitalis), sold under the brand name Lanoxin among others, is a medication used to treat various heart disease, heart conditions. Most frequently it is used for atrial fibrillation, atrial flutter, and heart failure. ...
-like
cardiac glycoside Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses include treatments for ...
s, and ingestion of these toxins can be fatal. Ingestion of ''Bufo'' toad poison and eggs by humans has resulted in several reported cases of poisoning, some of which resulted in death. A court case in Spain, involving a physician who dosed people with smoked Mexican Toad poison, one of his customers died after inhaling three doses, instead of the usual of only one, had images of intoxicated with this smoke suffering obvious hypocalcemic hand muscular spasms. Reports in the mid-1990s indicated that bufotenin-containing toad secretions had appeared as a
street drug Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an Sub ...
, supposedly but in fact ''not'' an
aphrodisiac An aphrodisiac is a substance that increases libido, sexual desire, sexual attraction, sexual pleasure, or sexual behavior. These substances range from a variety of plants, spices, and foods to synthetic chemicals. Natural aphrodisiacs, such as ...
, ingested orally in the form of '' ch'an su'', or as a psychedelic, by smoking or orally ingesting ''Bufo'' toad secretions or dried ''Bufo'' skins. The use of ''chan'su'' and ''love stone'' (a related toad skin preparation used as an aphrodisiac in the
West Indies The West Indies is an island subregion of the Americas, surrounded by the Atlantic Ocean, North Atlantic Ocean and the Caribbean Sea, which comprises 13 independent island country, island countries and 19 dependent territory, dependencies in thr ...
) has resulted in several cases of poisoning and at least one death. The practice of orally ingesting toad poison has been referred to in popular culture and in the scientific literature as toad licking and has drawn media attention. Albert Most, founder of the defunct Church of the Toad of Light and a proponent of spiritual use of ''
Bufo alvarius The Colorado River toad (''Incilius alvarius''), also known as the Sonoran Desert toad, is a toad species found in northwestern Mexico and the southwestern United States. It is well known for its ability to exude toxins from glands within its sk ...
'' toxin, published a booklet in 1984 titled '' Bufo Alvarius: The Psychedelic Toad of the Sonoran Desert'' which explained how to extract and smoke the secretions. Bufotenin is also present in the skin secretion of three arboreal hylid frogs of the genus '' Osteocephalus'' ('' Osteocephalus taurinus'', ''
Osteocephalus oophagus ''Osteocephalus oophagus'' is a species of frogs in the family Hylidae found in Brazil, Colombia, French Guiana, Guyana, and possibly Suriname. Its natural habitat is subtropical or tropical moist lowland forests. It is also reported to produce ...
'', and '' Osteocephalus langsdorfii'') from the
Amazon Amazon most often refers to: * Amazon River, in South America * Amazon rainforest, a rainforest covering most of the Amazon basin * Amazon (company), an American multinational technology company * Amazons, a tribe of female warriors in Greek myth ...
and Atlantic
rain forests Rainforests are forests characterized by a closed and continuous tree canopy, moisture-dependent vegetation, the presence of epiphytes and lianas and the absence of wildfire. Rainforests can be generally classified as tropical rainforests o ...
.


''Anadenanthera'' seeds

Bufotenin is a constituent of the
seeds In botany, a seed is a plant structure containing an embryo and stored nutrients in a protective coat called a ''testa''. More generally, the term "seed" means anything that can be sown, which may include seed and husk or tuber. Seeds are the ...
of ''
Anadenanthera colubrina ''Anadenanthera colubrina'' (also known as vilca, huilco, huilca, wilco, willka, curupay, curupau, cebil, or angico) is a South American tree closely related to yopo, or ''Anadenanthera peregrina''. It grows to tall and the trunk is very thorn ...
'' and ''
Anadenanthera peregrina ''Anadenanthera peregrina'', also known as yopo, jopo, cohoba, parica or calcium tree, is a perennial tree of the genus ''Anadenanthera'' native to the Caribbean and South America. It grows up to tall, and has a thorny bark. Its flowers grow ...
'' trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff preparations by indigenous cultures of the Caribbean, Central and South America since pre-Columbian times. The oldest archaeological evidence of use of ''Anadenanthera'' beans is over 4,000 years old.


Other sources

Bufotenin has been identified as a component in the latex of the takini ('' Brosimum acutifolium'') tree, which is used as a psychedelic by South American shamans, and in the seeds of ''
Mucuna pruriens ''Mucuna pruriens'' is a tropical legume native to Africa and tropical Asia and widely naturalized and cultivated. Its English common names include monkey tamarind, velvet bean, Bengal velvet bean, Florida velvet bean, Mauritius velvet bean, Yok ...
''. Bufotenin has also been identified in ''
Amanita muscaria ''Amanita muscaria'', commonly known as the fly agaric or fly amanita, is a basidiomycete fungus of the genus ''Amanita''. It is a large white-lamella (mycology), gilled, white-spotted mushroom typically featuring a bright red cap covered with ...
,'' '' Amanita citrina'', ''A. porphyria'', and ''A. tomentella''.


Occurrence in humans

Bufotenin occurs in trace amounts in the human body. It can be biosynthesized from
serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
by indolethylamine ''N''-methyltransferase (INMT)
enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
s.


Association with psychiatric conditions

A study conducted in the late 1960s reported the detection of bufotenin in the urine of schizophrenic subjects; however, subsequent research failed to confirm these findings until 2010. Studies have detected endogenous bufotenin in urine specimens from individuals with other psychiatric disorders, such as infant autistic patients. Another study indicated that paranoid violent offenders or those who committed violent behaviour towards family members have higher bufotenin levels in their urine than other violent offenders. A 2010 study utilized a
mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used ...
approach to detect levels of bufotenin in the urine of individuals with severe autism spectrum disorder (ASD), schizophrenia, and asymptomatic subjects. Their results indicate significantly higher levels of bufotenin in the urine of the ASD and schizophrenic groups when compared to asymptomatic individuals.


History

Bufotenine was first
isolated Isolation is the near or complete lack of social contact by an individual. Isolation or isolated may also refer to: Sociology and psychology *Social isolation *Isolation (psychology), a defense mechanism in psychoanalytic theory *Emotional iso ...
from
secretion Secretion is the movement of material from one point to another, such as a secreted chemical substance from a cell or gland. In contrast, excretion is the removal of certain substances or waste products from a cell or organism. The classical mec ...
s of the
toad Toad (also known as a hoptoad) is a common name for certain frogs, especially of the family Bufonidae, that are characterized by dry, leathery skin, short legs, and large bumps covering the parotoid glands. In popular culture (folk taxonomy ...
'' Bufo vulgaris'' by
French French may refer to: * Something of, from, or related to France ** French language, which originated in France ** French people, a nation and ethnic group ** French cuisine, cooking traditions and practices Arts and media * The French (band), ...
scientist A scientist is a person who Scientific method, researches to advance knowledge in an Branches of science, area of the natural sciences. In classical antiquity, there was no real ancient analog of a modern scientist. Instead, philosophers engag ...
s Césaire Phisalix and Gabriel Bertrand in 1893.Bochner, R., & Goyffon, M. (2007). L’œuvre scientifique de Césaire Phisalix (1852-1906), découvreur du sérum antivenimeux. Bull Soc Herp Fr, 123, 15-46. https://www.icict.fiocruz.br/sites/www.icict.fiocruz.br/files/L%20oeuvre%20scientifique%20de%20Cesaire%20Phisalix%20(1852--1906)%20decouvreur%20du%20serum%20antivenimeux.pdfPhisalix C, Bertrand G (1893) Toxicité comparée du sang et du venin de crapaud commun, considérée au point de vue de la sécrétion interne des glandes cutanées de cet animal. C R Soc Biol 45:477–479. https://scholar.google.com/scholar?cluster=14905926340091797397 It was also subsequently isolated from many other
natural source A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical sy ...
s, including
plant Plants are the eukaryotes that form the Kingdom (biology), kingdom Plantae; they are predominantly Photosynthesis, photosynthetic. This means that they obtain their energy from sunlight, using chloroplasts derived from endosymbiosis with c ...
s,
fungi A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified as one ...
, and other toads over time. The compound was first isolated to
purity Purity may refer to: Books * ''Pureza'' (novel), a 1937 Brazilian novel by José Lins do Rego * ''Purity'' (novel), a 2015 novel by Jonathan Franzen ** ''Purity'' (TV series), a TV series based on the novel *''Purity'', a 2012 novel by Jackson ...
by
Austrian Austrian may refer to: * Austrians, someone from Austria or of Austrian descent ** Someone who is considered an Austrian citizen * Austrian German dialect * Something associated with the country Austria, for example: ** Austria-Hungary ** Austria ...
chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a graduated scientist trained in the study of chemistry, or an officially enrolled student in the field. Chemists study the composition of ...
Hans Handovsky in 1920. The
chemical structure A chemical structure of a molecule is a spatial arrangement of its atoms and their chemical bonds. Its determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target m ...
of bufotenine was confirmed by
German German(s) may refer to: * Germany, the country of the Germans and German things **Germania (Roman era) * Germans, citizens of Germany, people of German ancestry, or native speakers of the German language ** For citizenship in Germany, see also Ge ...
chemist
Heinrich Wieland Heinrich Otto Wieland (; 4 June 1877 – 5 August 1957) was a German chemist. He won the 1927 Nobel Prize in Chemistry for his research into the bile acids. Career In 1901 Wieland received his doctorate at the University of Munich while studying ...
and colleagues in 1934. The first reported
synthesis Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors **Organic synthesis, the chemical synthesis of organi ...
of bufotenine was by
Japanese Japanese may refer to: * Something from or related to Japan, an island country in East Asia * Japanese language, spoken mainly in Japan * Japanese people, the ethnic group that identifies with Japan through ancestry or culture ** Japanese diaspor ...
researchers Toshio Hoshino and Kenya Shimodaira in 1935. Bufotenin was established as a major component of
hallucinogenic snuff A hallucinogenic snuff, or psychedelic snuff, is a powder prepared from plants containing psychedelic alkaloids and insufflated (snorted) to produce hallucinogenic effects. Hallucinogenic snuffs have been used as entheogens by indigenous peop ...
s made from ''
Anadenanthera peregrina ''Anadenanthera peregrina'', also known as yopo, jopo, cohoba, parica or calcium tree, is a perennial tree of the genus ''Anadenanthera'' native to the Caribbean and South America. It grows up to tall, and has a thorny bark. Its flowers grow ...
'' such as
cohoba Cohoba is a Taíno transliteration for a ceremony in which the ground seeds of the ''cojóbana'' tree (''Anadenanthera'' spp.) were used as a hallucinogenic snuff, snuff via a Y-shaped snuff tray, snuff tube. Use of this substance produced a hall ...
and
yopo ''Anadenanthera peregrina'', also known as yopo, jopo, cohoba, parica or calcium tree, is a perennial tree of the genus ''Anadenanthera'' native to the Caribbean and South America. It grows up to tall, and has a thorny bark. Its flowers grow ...
in 1954. It was also isolated from ''
Anadenanthera colubrina ''Anadenanthera colubrina'' (also known as vilca, huilco, huilca, wilco, willka, curupay, curupau, cebil, or angico) is a South American tree closely related to yopo, or ''Anadenanthera peregrina''. It grows to tall and the trunk is very thorn ...
'' in 1955.
Clinical studies Clinical trials are prospective biomedical or behavioral research studies on human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel vaccines, drugs, dietar ...
assessed the effects of bufotenin and were published starting in 1956. However, the findings of these studies were conflicting, and bufotenin developed a long-standing reputation of being non-
hallucinogen Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mo ...
ic as well as
toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...
. In any case, bufotenin nonetheless became a Schedule I
controlled substance A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Sing ...
in the
United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...
in 1967.
American American(s) may refer to: * American, something of, from, or related to the United States of America, commonly known as the "United States" or "America" ** Americans, citizens and nationals of the United States of America ** American ancestry, p ...
ethnobotanist Ethnobotany is an interdisciplinary field at the interface of natural and social sciences that studies the relationships between humans and plants. It focuses on traditional knowledge of how plants are used, managed, and perceived in human societi ...
Jonathan Ott Jonathan Ott (born 1949 in Hartford, Connecticut) is an ethnobotanist, writer, translator, publisher, natural products chemist and botanical researcher in the area of entheogens and their cultural and historical uses, and helped coin the term "' ...
and colleagues subsequently showed in 2001 that bufotenin is in fact a psychedelic and does not necessarily produce major
adverse effect An adverse effect is an undesired harmful effect resulting from a medication or other intervention, such as surgery. An adverse effect may be termed a "side effect", when judged to be secondary to a main or therapeutic effect. The term compli ...
s, although marked
nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...
and
vomiting Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pre ...
are prominent. Bufotenin was first encountered as a novel
recreational drug Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an Sub ...
in 1992.
Journalist A journalist is a person who gathers information in the form of text, audio or pictures, processes it into a newsworthy form and disseminates it to the public. This is called journalism. Roles Journalists can work in broadcast, print, advertis ...
Hamilton Morris Hamilton Morris (born April 14, 1987) is an American journalist, documentarian, and scientific researcher. He is the creator and director of the television series ''Hamilton's Pharmacopeia'', in which he investigated the chemistry, history, and ...
corroborated Ott and colleagues' findings on the hallucinogenicity of bufotenin in the early 2020s.


Society and culture


Names

Bufotenin, or bufotenine, is also known by the names 5-hydroxy-''N'',''N''-dimethyltryptamine (5-HO-DMT), ''N'',''N''-dimethyl-5-hydroxytryptamine, dimethylserotonin, and mappine, among others.


Recreational use

Bufotenin has been encountered as a
recreational drug Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an Sub ...
in forensic samples, for instance in
New York City New York, often called New York City (NYC), is the most populous city in the United States, located at the southern tip of New York State on one of the world's largest natural harbors. The city comprises five boroughs, each coextensive w ...
.


Legal status


Australia

Bufotenin is classified as a Schedule I controlled substance according to the Criminal Code Regulations of the Government of the Commonwealth of Australia. It is also listed as a Schedule 9 substance under the Poisons Standard (October 2015).Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534 A schedule 9 drug is outlined in the Poisons Act 1964 as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO." Under the Misuse of Drugs Act 1981 is determined to be enough for court of trial and is considered intent to sell and supply.


Sweden

Sweden's public health agency suggested classifying Bufotenin as a hazardous substance, on May 15, 2019.


United Kingdom

In the United Kingdom, bufotenin is a Class A drug under the 1971 Misuse of Drugs Act.


United States

Bufotenin (DEA Drug Code 7403) is regulated as a Schedule I drug by the
Drug Enforcement Administration The Drug Enforcement Administration (DEA) is a Federal law enforcement in the United States, United States federal law enforcement agency under the U.S. Department of Justice tasked with combating illicit Illegal drug trade, drug trafficking a ...
at the federal level in the
United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...
and is therefore illegal to buy, possess, and sell.§1308.11 Schedule I.
deadiversion.usdoj.gov


Research

Bufotenin is being investigated as a potential
pharmaceutical drug Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...
by the
Usona Institute The Usona Institute is a 501(c)(3) non-profit medical research organization (MRO) which is developing psychedelic drugs for potential medical use. It was launched by scientist and entrepreneur Bill Linton, who is the founder of the biotechnology ...
. As of May 2025, it is in the discovery or
preclinical research In drug development, preclinical development (also termed preclinical studies or nonclinical studies) is a stage of research that begins before clinical trials (testing in humans) and during which important feasibility, iterative testing and dr ...
stage of development. Bufotenin has shown
antiviral Antiviral drugs are a class of medication used for treating viral infections. Most antivirals target specific viruses, while a broad-spectrum antiviral is effective against a wide range of viruses. Antiviral drugs are a class of antimicrobials ...
activity against the
rabies virus Rabies virus (''Lyssavirus rabies'') is a neurotropic virus that causes rabies in animals, including humans. It can cause violence, hydrophobia, and fever. Rabies transmission can also occur through the saliva of animals and less commonly throu ...
and has been found to increase survival rates against
rabies Rabies is a viral disease that causes encephalitis in humans and other mammals. It was historically referred to as hydrophobia ("fear of water") because its victims panic when offered liquids to drink. Early symptoms can include fever and abn ...
in rodents.


See also

* List of entheogens


References


External links


Bufotenin - Isomer Design

Bufotenin - PsychonautWiki

Erowid - Bufotenin

The Big & Dandy Bufotenine (5-HO-DMT) Thread - Bluelight

Bufotenin - TiHKAL - Erowid

Bufotenin - TiHKAL - Isomer Design

Bufotenin - Trout's Notes

Psychoactive Toad Venom (Bufo Alvarius) - Tripsitter

Yopo (Anadenanthera peregrina): Psychedelic Snuff From the Amazon - Tripsitter
{{Tryptamines 5-HT1A agonists 5-HT2A agonists 5-HT2C agonists 5-HT3 agonists 5-HT4 agonists Amphibian toxins N,N-Dialkyltryptamines Emetics Entheogens 5-Hydroxytryptamines Peripherally selective drugs Plant toxins Psychedelic tryptamines Serotonin receptor agonists Serotonin releasing agents Substances discovered in the 1930s Tryptamine alkaloids