Diisopropyltryptamine (DiPT), also known as ''N'',''N''-diisopropyltryptamine, is a

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 ...

hallucinogenic drug 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, moo ...

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 that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily

aural Hearing, or auditory perception, is the ability to perceive sounds through an organ, such as an ear, by detecting vibrations as periodic changes in the pressure of a surrounding medium. The academic field concerned with hearing is auditory s ...

Dosage

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 ...

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 ...

'' gave a dosage range of DiPT of 25 to 100mg

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 ...

and a duration of 6 to 8hours. 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 ...

dose range for DiPT of 15 to 150mg or more has also been reported.

Effects

DiPT's effects are primarily aural. At lower doses,

reported effects similar to a

flanging Flanging is an audio signal processing, audio effect produced by mixing two identical audio signal, signals together, one signal delayed by a small and (usually) gradually changing period, usually smaller than 20 milliseconds. This produces a ...

or a

phase shift In physics and mathematics, the phase (symbol φ or ϕ) of a wave or other periodic function F of some real variable t (such as time) is an angle-like quantity representing the fraction of the cycle covered up to t. It is expressed in such a s ...

. At medium and higher dosages, the effect of DiPT is typically a radical shift downward in perceived pitch. This shift tends to be

nonlinear In mathematics and science, a nonlinear system (or a non-linear system) is a system in which the change of the output is not proportional to the change of the input. Nonlinear problems are of interest to engineers, biologists, physicists, mathe ...

, in that the shift downwards varies in relation to the initial pitch. This can produce bizarre sounds and render music disharmonious. There has been an experiment involving subjects with

perfect pitch Perfect commonly refers to: * Perfection; completeness, and excellence * Perfect (grammar), a grammatical category in some languages Perfect may also refer to: Film and television * ''Perfect'' (1985 film), a romantic drama * ''Perfect'' (20 ...

, the goal of which was to determine whether the pitch difference is truly distortive or linear, the results of which indicated that there is no clear relationship between perceived pitch and actual pitch. Aside from these, the most prevalent non-auditory effect is inner ear pressure (which has been painful in some instances, for example when combined with

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 ...

Interactions

Pharmacology

Pharmacodynamics

DiPT binds to

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 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, 5-HT_2B, 5-HT_2C receptors among others. It is known to act as a

full agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the agoni ...

of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors. It is also 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 ...

. In contrast to many related drugs, DiPT does not interact with the rodent or human

trace amine-associated receptor 1 Trace amine-associated receptor 1 (TAAR1) is a trace amine-associated receptor (TAAR) protein that in humans is encoded by the ''TAAR1'' gene. TAAR1 is a primarily intracellular amine-activated and G protein-coupled receptor (GPCR) that is p ...

(TAAR1). The discriminative stimulus properties of DiPT 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 are partially blocked 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.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 ...

and by the serotonin 5-HT_2C receptor antagonist

SB-242084 SB-242084 is a selective antagonist of the serotonin 5-HT2C receptor which is used in scientific research. It has anxiolytic effects-like effects in rodents, and enhances dopamine signalling in the limbic system, as well as having complex effe ...

. This is in contrast to the case of the related 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), wherein volinanserin fully blocks its stimulus properties and SB-242084 has minimal influence. Similarly to DMT and other psychedelics, 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, and this effect is blocked by volinanserin.

Chemistry

DiPT is a derivative of tryptamine formed by substituting

isopropyl In organic chemistry, a propyl group is a three-carbon alkyl substituent with chemical formula for the linear form. This substituent form is obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent ...

groups for the two hydrogen atoms attached to the non-aromatic nitrogen atom in the tryptamine molecule. Analogues of DiPT include

(DMT),

diethyltryptamine DET, also known under its chemical name ''N'',''N''-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET. DET, alongside DMT, was placed into the UN Schedule 1 list of illegal drugs in the 1970s, and is unco ...

(DET),

dipropyltryptamine ''N'',''N''-Dipropyltryptamine (DPT) is a psychedelic drug and entheogen belonging to the tryptamine family. Use as a designer drug has been documented by law enforcement officials since as early as 1968. However, potential therapeutic use was n ...

(DPT),

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 ...

, 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 ...

5-MeO-DiPT 5-MeO-DiPT, also known as 5-methoxy-''N'',''N''-diisopropyltryptamine and sometimes as foxy methoxy or simply foxy, is a psychedelic drug of the tryptamine and 5-methoxytryptamine families. It is the 5-methoxy derivative of diisopropyltryptami ...

4-HO-DiPT 4-HO-DiPT, also known as 4-hydroxy-''N'',''N''-diisopropyltryptamine or as iprocin, is a synthetic compound, synthetic psychedelic drug of the substituted tryptamine, tryptamine family. It is a higher homologous series, homologue of psilocin and ...

(iprocin), 5-HO-DiPT,

4-AcO-DiPT 4-Acetoxy-DiPT, also known as 4-acetoxy-''N'',''N''-diisopropyltryptamine or as ipracetin, is a synthetic psychedelic tryptamine. It is relatively uncommon and has only a short history of human use. Interactions Chemistry 4-AcO-DiPT is a trypta ...

(ipracetin), and

5,6-MDO-DiPT 5,6-MDO-DiPT, or 5,6-methylenedioxy-''N'',''N''-diisopropyltryptamine, is a lesser-known psychedelic drug. It is the 5,6-methylenedioxy analog of DiPT. 5,6-MDO-DiPT was first synthesized by Alexander Shulgin. It is mentioned in his book ''TiHKAL ...

, among others.

Legal status

United Kingdom

As is the case with many psychedelic tryptamines and phenethylamines, it is Class A in the UK, making it illegal to possess or use.

United States

DiPT is not scheduled 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 ...

, but it could be considered an analog of

, in which case purchase, sale, or possession for human consumption or illicit use that is not for scientific or industrial purposes could be prosecuted under the

Federal Analog Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...

. Some of the people arrested in

Operation Web Tryp Operation Web Tryp was a United States Drug Enforcement Administration operation that ended on July 21, 2004 with the arrests of 10 persons. Its purpose was to investigate web sites suspected of distribution of unscheduled, unregulated tryptamine ...

were selling DiPT, however the drug is not explicitly forbidden or outlawed. However the US Drug Enforcement Agency (DEA) withdrew a proposal to ban five psychedelic substances including 4-Hydroxy-N,N-diisopropyltryptamine (4-OH-DiPT), N-Isopropyl-5-Methoxy-N-Methyltryptamine (5-MeO-MiPT) and N,N-Diisopropyltryptamine (DiPT). DEA withdrew the proposed listing as schedule 1 banned substance after a public hearing in 2022.

Florida

"DiPT (N,N-Diisopropyltryptamine)" is 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 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 in Florida.

Sweden

Sweden's public health agency suggested classifying DiPT as a

hazardous substance Dangerous goods are substances that are a risk to health, safety, property or the environment during transport. Certain dangerous goods that pose risks even when not being transported are known as hazardous materials ( syllabically abbreviate ...

, on May 15, 2019.

References

External links

DiPT - Isomer Design

DiPT - PsychonautWiki

DiPT - Erowid

The Big & Dandy DiPT Thread - Bluelight

DIPT - TiHKAL - Erowid

DIPT - TiHKAL - Isomer Design

Forget the Visuals—Psychedelic DiPT Makes You Trip On Sound - Double Blind Magazine

What Is DiPT? The Auditory Psychedelic - Tripsitter
{{Tryptamines 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists Designer drugs N,N-Dialkyltryptamines Diisopropylamino compounds Psychedelic tryptamines Serotonin receptor agonists Serotonin reuptake inhibitors