5-MeO-αMT, also known as 5-methoxy-α-methyltryptamine or as α,''O''-dimethylserotonin (α,''O''-DMS or Alpha-O), 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 ...

α-alkyltryptamine 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

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 ...

families. 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 α-methyltryptamine (αMT) and an analogue 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 ...

. The drug is said to be the most potent psychedelic of the simple indolealkylamines (i.e., tryptamines). It is active at

oral 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 ora ...

doses of 2 to 4mg.

Use

The dosage range of 5-MeO-AMT listed in ''

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 ...

'' is 2.5 to 4.5mg and its duration is listed as 12 to 18hours. However, a wider

recreational Recreation is an activity of leisure, leisure being discretionary time. The "need to do something for recreation" is an essential element of human biology and psychology. Recreational activities are often done for enjoyment, amusement, or plea ...

dosage range of 0.5 to 15mg has also been reported. 5-MeO-AMT has supposedly been sold as 4mg tablets by the street name Alpha-O and taken 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 ...

. Since the

DEA The Drug Enforcement Administration (DEA) is a United States federal law enforcement agency under the U.S. Department of Justice tasked with combating illicit drug trafficking and distribution within the U.S. It is the lead agency for domes ...

arrests of the makers of a huge percentage of the United States'

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 ...

in 2000, 5-MeO-AMT may have occasionally been sold under the guise of LSD in liquid,

sugar cube Sugar cubes are white sugar granules pressed into small cubes measuring approximately 1 teaspoon each. They are usually used for sweetening drinks such as tea and coffee. They were invented in the early 19th century in response to the difficulti ...

, or blotter form, though this may be due to DEA reports of finding it on sugar cubes and blotters like LSD. The most common route of administration for 5-MeO-AMT is orally. Anecdotal reports, however, have described snorting or smoking the substance. Intravenous (IV) and intramuscular (IM) routes are rarely, if ever, used outside research settings due to the high potency, powerful effects and quicker onset.

Effects

Erowid Erowid, also called Erowid Center, is a non-profit educational organization that provides information about psychoactive plants and chemicals. Erowid documents legal and illegal substances, including their intended and adverse effects. Inform ...

lists the following effects:

Positive

* Increased energy * Improved mood heading into euphoria at higher doses * Increased sociability, gregariousness * Increased giggling and laughter * Increased sense of

creative thinking Creativity is the ability to form novel and valuable ideas or works using one's imagination. Products of creativity may be intangible (e.g. an idea, scientific theory, literary work, musical composition, or joke), or a physical object (e.g. a ...

* Increased pleasure from sense of touch * Intensification of sex for some users

Neutral

* Lightheadedness * Brightening of

color Color (or colour in English in the Commonwealth of Nations, Commonwealth English; American and British English spelling differences#-our, -or, see spelling differences) is the visual perception based on the electromagnetic spectrum. Though co ...

s * Visuals including

motion In physics, motion is when an object changes its position with respect to a reference point in a given time. Motion is mathematically described in terms of displacement, distance, velocity, acceleration, speed, and frame of reference to an o ...

wave In physics, mathematics, engineering, and related fields, a wave is a propagating dynamic disturbance (change from List of types of equilibrium, equilibrium) of one or more quantities. ''Periodic waves'' oscillate repeatedly about an equilibrium ...

s, breathing walls, etc. (usually at higher doses, over 4–5 mg) * Increased attention to detail * Auditory distortions and/or hallucinations (usually at higher doses)

Negative

Headache A headache, also known as cephalalgia, is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of Depression (mood), depression in those with severe ...

* Body

fatigue Fatigue is a state of tiredness (which is not sleepiness), exhaustion or loss of energy. It is a signs and symptoms, symptom of any of various diseases; it is not a disease in itself. Fatigue (in the medical sense) is sometimes associated wit ...

* Chills from elevated body temperature (potential dehydration) * Stress and extreme fatigue from long duration of effects. *

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 ...

diarrhea Diarrhea (American English), also spelled diarrhoea or diarrhœa (British English), is the condition of having at least three loose, liquid, or watery bowel movements in a day. It often lasts for a few days and can result in dehydration 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 ...

* Difficulty

sleep Sleep is a state of reduced mental and physical activity in which consciousness is altered and certain Sensory nervous system, sensory activity is inhibited. During sleep, there is a marked decrease in muscle activity and interactions with th ...

ing or resting for 12–24 hours after ingestion. *

Paranoia Paranoia is an instinct or thought process that is believed to be heavily influenced by anxiety, suspicion, or fear, often to the point of delusion and irrationality. Paranoid thinking typically includes persecutory beliefs, or beliefs of co ...

, irritability,

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 ...

(increasing with dose). * Delusional, aggressive, or dissociated behaviour at very high doses (20+ mg) * Risk of death

Dangers

If misrepresented as LSD, 5-MeO-AMT can be extremely dangerous; users may take a number of "hits" of 5-MeO-AMT, assuming that it is LSD. Unlike LSD, which is very safe in overdose, 5-MeO-AMT can be very harmful or fatal. Particularly sensitive individuals can experience symptoms of overdose at dosages in the normal (for most users) range — as low as 20 mg. This has led to at least a few hospitalizations and possibly more than one death. It is likely that the overdose potential of the compound is due to its sympathomimetic effects, as the side effects noted in overdose cases include

cardiac arrhythmia Arrhythmias, also known as cardiac arrhythmias, are irregularities in the heartbeat, including when it is too fast or too slow. Essentially, this is anything but normal sinus rhythm. A resting heart rate that is too fast – above 100 beat ...

and

seizure A seizure is a sudden, brief disruption of brain activity caused by abnormal, excessive, or synchronous neuronal firing. Depending on the regions of the brain involved, seizures can lead to changes in movement, sensation, behavior, awareness, o ...

. It also seems that oral consumption is safer than

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 ...

. Gloria Discerni, 18, died after overdosing on a drug initially believed to be LSD. Authorities learned months later that the drug wasn't LSD but a "designer drug" identified as 5-MeO-AMT.

Interactions

Pharmacology

Pharmacodynamics

5-MeO-AMT acts as a 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 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-HT_1A, 5-HT_2A, and 5-HT_2B receptors, among others. Its at the serotonin 5-HT_2A receptor has been found to be 2 to 8.4nM. In relation to this, it is an extremely potent agonist of the serotonin 5-HT_2A 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 ...

'', showing the highest potency of any other tryptamine assessed in one study. Its potency in activating the serotonin 5-HT_2A receptor was 38-fold higher than that 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) and 361-fold higher than that of

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 ...

in the same study. It is also a highly potent agonist of the serotonin 5-HT_2B receptor, with an of 4nM. Whereas

(5-hydroxytryptamine), and αMT show potent activity as

monoamine releasing agent A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrati ...

s, including of

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 ...

, and/or

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 ...

, the monoamine-releasing activity of 5-methoxylated tryptamine derivatives, like

5-MeO-NMT 5-MeO-NMT, also known as 5-methoxy-''N''-methyltryptamine, is an organic chemical compound, being the 5-methoxy analogue of ''N''-methyltryptamine (NMT). It was first isolated from ''Phalaris arundinacea'' (reed canary grass) and also occurs in o ...

, and

among others, is dramatically reduced or abolished. Accordingly, whereas the values of αMT for induction of monoamine release are 22 to 68nM for serotonin, 79 to 112nM for norepinephrine, and 79 to 180nM for dopamine, the values in the case of 5-MeO-AMT are 460nM for serotonin, 8,900nM for norepinephrine, and 1,500nM for dopamine. Similarly, it is of very low potency as a

monoamine reuptake inhibitor A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamin ...

( values >1,000nM). Considering the very high potency of 5-MeO-AMT in activating the serotonin 5-HT_2A receptor, its weak activities as a monoamine releasing agent and reuptake inhibitor are of questionable significance. 5-MeO-AMT is a weak

monoamine oxidase A Monoamine oxidase A, also known as MAO-A, is an enzyme ( E.C. 1.4.3.4) that in humans is encoded by the ''MAOA'' gene. This gene is one of two neighboring gene family members that encode mitochondrial enzymes which catalyze the oxidative dea ...

(MAO-A)

inhibitor Inhibitor or inhibition may refer to: Biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotransmi ...

, with an of 31,000nM. For comparison, the of AMT for MAO-A inhibition was 380nM (~82-fold more potent than 5-MeO-AMT) and the values of

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

(and its

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

s) for MAO-A inhibition have been reported to be 11,000 to 70,000nM. 5-MeO-AMT 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 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, in rodents, and this is reversed by the serotonin 5-HT_2A 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.ketanserin Ketanserin, sold under the brand name Sufrexal, is an antihypertensive agent which is used to treat arterial hypertension and vasospasm, vasospastic disorders. It is also used in scientific research as an antiserotonergic medication, agent in th ...

. It substitutes for other psychedelics such as DOM and

in animal

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, but does not substitute for

entactogen Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observe ...

s like

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used ...

psychostimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition ...

s like

dextromethamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational or performance-enhancing drug and less commonly as a second-line treatment for attention deficit hyperactivity di ...

cocaine Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...

. In contrast to other psychedelics, 5-MeO-AMT has been found to not fully substitute for other psychedelics including DOM, LSD, and

(DMT), but did partially generalize to LSD (67% responding). This is analogous to findings with

, which has a major serotonin 5-HT_2A receptor-mediated component to its discriminative stimulus properties. 5-MeO-AMT does not produce

locomotor hyperactivity Locomotor activity is a measure of animal behavior which is employed in scientific research. Hyperlocomotion, also known as locomotor hyperactivity, hyperactivity, or increased locomotor activity, is an effect of certain drugs in animals in whi ...

behavioral sensitization Addiction is a neuropsychological disorder characterized by a persistent and intense urge to use a drug or engage in a behavior that produces natural reward, despite substantial harm and other negative consequences. Repetitive drug use can ...

conditioned place preference Conditioned place preference (CPP) is a form of Pavlovian conditioning used to measure the motivational effects of objects or experiences. This motivation comes from the pleasurable aspect of the experience, so that the brain can be reminded of th ...

, or

self-administration Self-administration is, in its Medicine, medical sense, the process of a subject administering a Pharmacology, pharmacological substance to themself. A clinical example of this is the subcutaneous "self-injection" of insulin by a Diabetes, diabetic ...

, further indicating a lack of psychostimulant-like effects as well as

misuse potential Substance misuse, also known as drug misuse or, in older vernacular, substance abuse, is the use of a drug in amounts or by methods that are harmful to the individual or others. It is a form of substance-related disorder, differing definitions ...

. Instead, 5-MeO-AMT produces

hypolocomotion Locomotor activity is a measure of animal behavior which is employed in scientific research. Hyperlocomotion, also known as locomotor hyperactivity, hyperactivity, or increased locomotor activity, is an effect of certain drugs in animals in whi ...

. 5-MeO-AMT is known to produce sympathomimetic effects, but these effects likely depend on serotonin 5-HT_2A receptor activation rather than on monoamine release or reuptake inhibition. Other serotonergic psychedelics are also well known to produce sympathomimetic effects.

Chemistry

5-MeO-AMT, also known as 5-methoxy-α-methyltryptamine, 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 ...

. It is a derivative of

(T),

(5-MeO-T or 5-MT), and α-methyltryptamine (AMT or αMT) and is an analogue of other tryptamines like α-methylserotonin (5-HO-AMT) and

. Some derivatives of 5-MeO-AMT include α,''N''-dimethyl-5-methoxytryptamine (5-MeO-α-Me-NMT or α,''N'',''O''-TMS) and α,''N'',''N''-trimethyl-5-methoxytryptamine (5-MeO-α-Me-DMT or α,''N'',''N'',''O''-TMS). As noted by

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 ...

, the α-methylated

s can be looked at as the tryptamine homologues of the

s (α-methylated phenethylamines). 5-MeO-AMT is

soluble In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solubi ...

water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...

and

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

but not in

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

History

5-MeO-AMT was first synthesized and described in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

in 1958. Its psychedelic effects in humans were first observed in 1976 and were described by

and

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 ...

and colleagues by 1978.

Society and culture

Legal status

Australia

5-MeO-AMT is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). A Schedule 9 substance is a substance 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 Commonwealth and/or State or Territory Health Authorities.

Sweden

''Sveriges riksdags'' health ministry ''Statens folkhälsoinstitut'' classified 5-MeO-αMT as "health hazard" under the act ''Lagen om förbud mot vissa hälsofarliga varor'' (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') as of Oct 1, 2004, in their regulation SFS 2004:696 listed as 5-metoxi-alfametyltryptamin (5-MeO-AMT), making it illegal to sell or possess.

United Kingdom

5-MeO-αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT. This was following the events of 10 June 2014 when the Advisory Council on the Misuse of Drugs recommended that 5-MeO-αMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.

United States

5-MeO-AMT is unscheduled 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 ...

. However, the DEA considers the chemical a controlled substance analogue. The agency's opinion on this matter may change at any time.

=Florida

= 5-MeO-AMT is a Schedule I controlled substance in the state of

Florida Florida ( ; ) is a U.S. state, state in the Southeastern United States, Southeastern region of the United States. It borders the Gulf of Mexico to the west, Alabama to the northwest, Georgia (U.S. state), Georgia to the north, the Atlantic ...

, making it illegal to buy, sell, or possess.

References

External links

DEA forensic journal on 5-MeO-AMT

Erowid 5-MeO-AMT vault

Lycaeum 5-MeO-AMT page

TiHKAL entry

5-MeO-AMT (α,''O''-DMS) entry in TiHKAL • info
{{Tryptamines 5-HT1A agonists 5-HT2A agonists 5-HT2B agonists Alpha-Alkyltryptamines Designer drugs 5-Methoxytryptamines Monoamine oxidase inhibitors Psychedelic tryptamines Serotonin-norepinephrine-dopamine releasing agents Serotonin receptor agonists

Use