5-MeO-DiPT, also known as 5-methoxy-''N'',''N''-diisopropyltryptamine and sometimes as foxy methoxy or simply foxy, is a

psychedelic drug 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 halluc ...

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 ...

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 the 5-

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position 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 ...

diisopropyltryptamine Diisopropyltryptamine (DiPT), also known as ''N'',''N''-diisopropyltryptamine, is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily ...

(DiPT).

Dosage

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 ...

'' and other publications,

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 ...

reported the dosage of 5-MeO-DiPT to be 6 to 12mg orally, its onset to be 20 to 30minutes, its time to peak effects to be 1 to 1.5hours, and its duration to be 4 to 8hours. The drug can also be used

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 ...

Effects

The effects of 5-MeO-DiPT are reported to include

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 ...

-like effects and pro-sexual effects, among others. It is said to be associated with relatively few

visual The visual system is the physiological basis of visual perception (the ability to detect and process light). The system detects, transduces and interprets information concerning light within the visible range to construct an image and buil ...

changes. Only at higher doses have

closed-eye visual Closed-eye hallucinations and closed-eye visualizations (CEV) are hallucinations that occur when one's eyes are closed or when one is in a darkened room. They should not be confused with phosphenes, perceived light and shapes when pressure is ap ...

s occurred. On the other hand, 5-MeO-DiPT is said to produce some of the

auditory distortion Sensory processing disorder (SPD), formerly known as sensory integration dysfunction, is a condition in which multisensory input is not adequately processed in order to provide appropriate responses to the demands of the environment. Sensory ...

s that

DiPT Diisopropyltryptamine (DiPT), also known as ''N'',''N''-diisopropyltryptamine, is a Psychedelic drug, psychedelic Psychedelics, dissociatives and deliriants, hallucinogenic drug of the substituted tryptamine, tryptamine family that has a unique ...

is associated with. 5-MeO-DiPT is reported to be more like a

stimulant 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, ...

, party drug, and sexual enhancer than a psychedelic. Other effects include somatic sensual activation, talkativeness,

disinhibition Disinhibition, also referred to as behavioral disinhibition, is medically recognized as an orientation towards immediate gratification, leading to impulsive behaviour driven by current thoughts, feelings, and external stimuli, without regard for ...

, emotional enhancement, easier emotional expression and communication, and intellectual activation. The emotional enhancement is described as similar to that of

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 ...

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 5-MeO-DiPT include slight

mydriasis Mydriasis is the Pupillary dilation, dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, Physical trauma, trauma, or the use of c ...

(pupil dilation) among others.

Overdose

Excessive doses have caused clinical intoxication, characterized by nausea, vomiting, agitation, hypotension, mydriasis, tachycardia and hallucinations, in a number of young adults. A number of these overdoses are attributed to the drug’s extended onset of action, where first time users, who were unfamiliar with the drug, administered a second dose after initially feeling no effects.

Rhabdomyolysis Rhabdomyolysis (shortened as rhabdo) is a condition in which damaged skeletal muscle breaks down rapidly. Symptoms may include muscle pains, weakness, vomiting, and confusion. There may be tea-colored urine or an irregular heartbeat. Some o ...

and renal failure occurred in one young man and another one died 3–4 hours after an apparent rectal overdose. At least one death has been attributed to consumption of 5-MeO-DiPT.

Interactions

Pharmacology

Pharmacodynamics

The mechanism that produces the purported hallucinogenic and entheogenic effects of 5-MeO-DiPT is thought to result primarily from 5-HT_2A receptor

agonism Agonism (from Greek 'struggle') is a political and social theory that emphasizes the potentially positive aspects of certain forms of conflict. It accepts a permanent place for such conflict in the political sphere, but seeks to show how indivi ...

, although additional mechanisms of action such as

monoamine oxidase inhibition Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, especia ...

(MAOI) may be involved also. The strongest receptor binding affinity for 5-MeO-DiPT is at the 5-HT_1A receptor. 5-MeO-DiPT 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

-like effects, in rodents. This is blocked by 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.volinanserin Volinanserin (INN; developmental code MDL-100,907) is a highly selective 5-HT2A receptor antagonist that is frequently used in scientific research to investigate the function of the 5-HT2A receptor. It was also tested in clinical trials as a p ...

. The drug produces a relatively weak head–twitch response, much lower in magnitude than that produced by for example

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 ...

or DOM. 5-MeO-DiPT also 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 ...

and

hypothermia Hypothermia is defined as a body core temperature below in humans. Symptoms depend on the temperature. In mild hypothermia, there is shivering and mental confusion. In moderate hypothermia, shivering stops and confusion increases. In severe ...

in rodents. It partially substitutes 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 ...

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 (52–75% responding at different doses). This could be completely blocked by volinanserin, whereas the serotonin 5-HT_1A receptor antagonist

WAY-100635 WAY-100635 is a piperazine drug and research chemical widely used in scientific studies. It was originally believed to act as a selective 5-HT1A receptor antagonist, but subsequent research showed that it also acts as potent full agonist at the ...

had no effect on the stimulus properties of 5-MeO-DiPT. 5-MeO-DiPT is a weak

serotonin reuptake inhibitor A serotonin reuptake inhibitor (SRI) is a type of drug which acts as a reuptake inhibitor of the neurotransmitter serotonin (5-hydroxytryptamine, or 5-HT) by blocking the drug action, action of the serotonin transporter (SERT). This in turn lea ...

. The elevations in serotonin levels caused by its serotonin reuptake inhibition are limited by its concomitant serotonin 5-HT_1A receptor agonism, as serotonin 5-HT_1A receptors serve as

inhibitory An inhibitory postsynaptic potential (IPSP) is a kind of synaptic potential that makes a Chemical synapse, postsynaptic neuron less likely to generate an action potential.Purves et al. Neuroscience. 4th ed. Sunderland (MA): Sinauer Associates, Inc ...

autoreceptor An autoreceptor is a type of Receptor (biochemistry), receptor located in the cell membrane, membranes of neuron, nerve cells. It serves as part of a negative feedback loop in signal transduction. It is only sensitive to the neurotransmitters or ...

s that limit serotonin release. 5-MeO-DiPT has been reported to be

neurotoxic Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specifical ...

in rats.

Pharmacokinetics

The

pharmacokinetics Pharmacokinetics (from Ancient Greek ''pharmakon'' "drug" and ''kinetikos'' "moving, putting in motion"; see chemical kinetics), sometimes abbreviated as PK, is a branch of pharmacology dedicated to describing how the body affects a specific su ...

and

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 ...

of 5-MeO-DiPT have been studied.

Chemistry

Analogues of 5-MeO-DiPT include

5-MeO-DiBF 5-MeO-DiBF is a psychedelic that has been sold online as a designer drug and was first definitively identified in December 2015 by a forensic laboratory in Slovenia. It is thought to act as an agonist for the 5-HT1A and 5-HT2 family of seroto ...

, 5-MeO-DPT,

5-MeO-AMT 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 of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families. It is a derivative of α ...

, and

5-MeO-MiPT 5-MeO-MiPT is a psychedelic and hallucinogen of the tryptamine family. It used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for ...

, as well as

DMT Dimethyltryptamine (DMT), also known as ''N'',''N''-dimethyltryptamine (''N'',''N''-DMT), is a serotonergic hallucinogen and investigational drug of the tryptamine family that occurs naturally in many plants and animals, including humans. D ...

, DPT, AMT,

DIPT Diisopropyltryptamine (DiPT), also known as ''N'',''N''-diisopropyltryptamine, is a Psychedelic drug, psychedelic Psychedelics, dissociatives and deliriants, hallucinogenic drug of the substituted tryptamine, tryptamine family that has a unique ...

, and MIPT, among others.

History

5-MeO-DiPT was discovered in the 1970s and was first described by

and colleagues in 1980. It started to be encountered as a novel

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 ...

and

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...

in 1999. The drug became a

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 2003.

Society and culture

Recreational use

Use of 5-MeO-DiPT has been found to be particularly prevalent among

gay men Gay men are male homosexuals. Some bisexual men, bisexual and homoromantic men may dually identify as ''gay'' and a number of gay men also identify as ''queer''. Historic terminology for gay men has included ''Sexual inversion (sexology), in ...

who use

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

Legal status

Canada

5-MeO-DiPT is not scheduled in

Canada Canada is a country in North America. Its Provinces and territories of Canada, ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, making it the world's List of coun ...

China

As of October 2015, 5-MeO-DiPT is a controlled substance in China.

Denmark

Illegal since February 2004.

Germany

Illegal since September 1999.

Greece

Illegal since February 2003.

Japan

Illegal since April 2005.

Singapore

Illegal since early 2006.

Sweden

''Sveriges riksdags'' health ministry ''Statens folkhälsoinstitut'' classified 5-MeO-DiPT 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-N,N-diisopropyltryptamin (5-MeO-DIPT), making it illegal to sell or possess.

United States

On April 4, 2003, 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 ...

added both 5-MeO-DiPT and alpha-methyltryptamine (AMT) to Schedule I of the

Controlled Substances Act The Controlled Substances Act (CSA) is the statute establishing federal government of the United States, federal drug policy of the United States, U.S. drug policy under which the manufacture, importation, possession, use, and distribution of ...

under "emergency scheduling" procedures. The drugs were officially placed into Schedule I on September 29, 2004. Prior to its prohibition in the U.S., 5-MeO-DiPT was sold online alongside psychoactive analogues such as

, and DPT, neither of which have yet been expressly outlawed.

References

External links

5-MeO-DiPT - Isomer Design

5-MeO-DiPT - PsychonautWiki

5-MeO-DIPT - Erowid

5-MeO-DiPT - TripSit

The Big & Dandy 5-MeO-DiPT Thread - Bluelight

5-MeO-DIPT - TiHKAL - Erowid

5-MeO-DIPT - TiHKAL - Isomer Design

{{DEFAULTSORT:Methoxy-N N-diisopropyltryptamine 5- 5-HT1A agonists 5-HT2A agonists 5-HT2C agonists Aphrodisiacs Designer drugs N,N-Dialkyltryptamines Diisopropylamino compounds 5-Methoxytryptamines Neurotoxins Phenol ethers Psychedelic tryptamines Serotonin receptor agonists Serotonin reuptake inhibitors