Diisopropyltryptamine

Last updated
Diisopropyltryptamine
DiPT.svg
DiPT-3d-sticks.png
Clinical data
Trade names Dipt.
Other namesN,N-Diisopropyltryptamine, DiPT
ATC code
  • none
Legal status
Legal status
  • AU:Unscheduled
  • CA:Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US:Unscheduled
Identifiers
  • 3-[2-(Diisopropylamino)ethyl]indole
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H24N2
Molar mass 244.382 g·mol−1
3D model (JSmol)
  • CC(C)N(CCc1c[nH]c2ccccc12)C(C)C
  • InChI=1S/C16H24N2/c1-12(2)18(13(3)4)10-9-14-11-17-16-8-6-5-7-15(14)16/h5-8,11-13,17H,9-10H2,1-4H3 Yes check.svgY
  • Key:ZRVAAGAZUWXRIP-UHFFFAOYSA-N Yes check.svgY
   (verify)

Diisopropyltryptamine ( /ˌdˌsˌprpɪlˈtrɪptəmn/ ; also known as N,N-diisopropyltryptamine or DiPT) 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 aural. [1]

Contents

Hallucinogenic properties

DiPT's effects are primarily aural. At lower doses, Alexander Shulgin reported effects similar to a flanging or a phase shift. 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 that the shift downwards varies in relation to the initial pitch. This can produce bizarre sounds and render music disharmonious. [1] There has been an experiment involving subjects with perfect pitch, 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. [1] 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). [1]

Chemistry

DiPT is a derivative of tryptamine formed by substituting isopropyl groups for the two hydrogen atoms attached to the non-aromatic nitrogen atom in the tryptamine molecule.

Pharmacodynamics

Binding sitesBinding affinity (Ki, μM) [2]
5-HT1A0.538
5-HT2A1.2
5-HT2C6.5
D1>25
D2>25
D3>25
α1A>12
α2A3.6
TAAR1>15
H10.92
SERT0.18
DAT4.1
NET8.9

United Kingdom

As is the case with many PiHKAL and TiHKAL drugs, 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, [3] but it could be considered an analog of 5-MeO-DiPT, 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. Some of the people arrested in Operation Web Tryp 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. [4]

Florida

"DiPT (N,N-Diisopropyltryptamine)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida. [5]

Sweden

Sweden's public health agency suggested classifying DiPT as a hazardous substance, on May 15, 2019. [6]

See also

Related Research Articles

<i>alpha</i>-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.

<span class="mw-page-title-main">Dipropyltryptamine</span> Chemical compound

N,N-Dipropyltryptamine (DPT) is a psychedelic 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 not investigated until the 1970s. It is found either as a crystalline hydrochloride salt or as an oily or crystalline base. It has not been found to occur endogenously. It is a close structural homologue of dimethyltryptamine and diethyltryptamine.

<span class="mw-page-title-main">5-MeO-DMT</span> Chemical compound

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, The power, and Toad venom.

5-Methoxy-<i>N</i>,<i>N</i>-diisopropyltryptamine Psychedelic tryptamine

5-Methoxy-N,N-diisopropyltryptamine is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).

<span class="mw-page-title-main">5-MeO-aMT</span> Chemical compound

5-MeO-aMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin (Alpha-O) is a potent psychedelic tryptamine. It is soluble in ethanol.

<span class="mw-page-title-main">4-HO-DiPT</span> Chemical compound

4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.

<span class="mw-page-title-main">5-MeO-MiPT</span> Chemical compound

5-MeO-MiPT is a psychedelic and hallucinogenic drug, 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 5-MeO-DiPT because of the very similar structure and effects.

<span class="mw-page-title-main">5-MeO-DET</span> Chemical compound

5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.

<span class="mw-page-title-main">4-HO-MiPT</span> Chemical compound

4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

<span class="mw-page-title-main">Methylisopropyltryptamine</span> Chemical compound

N-Methyl-N-isopropyltryptamine (MiPT) is a psychedelic tryptamine, closely related to DMT, DiPT and Miprocin.

<span class="mw-page-title-main">5-MeO-DPT</span> Chemical compound

5-MeO-DPT, is a psychedelic and entheogenic designer drug.

<i>N</i>-Methyltryptamine Chemical compound

N-Methyltryptamine (NMT) is a member of the substituted tryptamine chemical class and a natural product which is biosynthesized in the human body from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. It is a common component in human urine. NMT is an alkaloid derived from L-tryptophan that has been found in the bark, shoots and leaves of several plant genera, including Virola, Acacia, Mimosa, and Desmanthus—often together with the related compounds N,N-dimethyltryptamine (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).

<span class="mw-page-title-main">4-Hydroxy-5-methoxydimethyltryptamine</span> Chemical compound

4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a novel psychedelic drug. It is the 4-hydroxy counterpart of 5-MeO-DMT, or the 5-methoxy counterpart of psilocin.

<span class="mw-page-title-main">5-MeO-NMT</span> Chemical compound

5-MeO-NMT (5-methoxy-N-methyltryptamine) is an organic chemical compound, being the 5-methoxy analog of N-methyltryptamine (NMT). It was first isolated from Phalaris arundinacea. It has also been synthesized by Alexander Shulgin and reported in his book TiHKAL. Like other members of the N-methyltryptamine family of compounds, 5-MeO-NMT is believed to produce few or no psychedelic effects, although very little data exists about its pharmacological properties or toxicity.

<span class="mw-page-title-main">4,5-MDO-DiPT</span> Chemical compound

4,5-MDO-DiPT, or 4,5-methylenedioxy-N,N-diisopropyltryptamine, is a lesser-known psychedelic drug. It is the 4,5-methylenedioxy analog of DiPT. 4,5-MDO-DiPT was first synthesized by Alexander Shulgin. In his book TiHKAL, 4,5-MDO-DiPT produces slight LSD-like effects after several hours. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4,5-MDO-DiPT.

<span class="mw-page-title-main">4-HO-αMT</span> Chemical compound

4-Hydroxy-α-methyltryptamine (4-HO-αMT) is a psychedelic drug of the tryptamine class. It is a close structural analogue of α-methyltryptamine (αMT) and produces similar effects to it, but with exacerbated side effects similarly to 5-MeO-αMT. Alexander Shulgin describes 4-HO-αMT briefly in his book TiHKAL:

The 4-hydroxy analogue of αMT has been looked at in human subjects. It is reported to be markedly visual in its effects, with some subjects reporting dizziness and a depressed feeling. There were, however, several toxic signs at doses of 15 to 20 milligrams orally, including abdominal pain, tachycardia, increased blood pressure and, with several people, headache and diarrhea.

<span class="mw-page-title-main">4-MeO-DMT</span> Chemical compound

4-MeO-DMT (4-methoxy-N,N-dimethyltryptamine) is a tryptamine derivative which has some central activity in animal tests similar to that of related psychedelic tryptamine drugs, although with significantly lower potency than either 5-MeO-DMT or 4-hydroxy-DMT (psilocin).

<span class="mw-page-title-main">5-MeO-MALT</span> Chemical compound

5-MeO-MALT (5-methoxy-N-methyl-N-allyltryptamine) is a lesser-known psychedelic drug that is closely related to 5-MeO-DALT and has been sold online as a designer drug.

<span class="mw-page-title-main">MALT (psychedelic drug)</span> Chemical compound

MALT is a lesser-known drug from the tryptamine family. It is a novel compound with very little history of human use. It is closely related to methylpropyltryptamine (MPT), as well as N-methyltryptamine. It has been sold online as a designer drug. Very little information on the pharmacology or toxicity of MALT is available.

References

  1. 1 2 3 4 Shulgin A (1997). TiHKAL: Tryptamines I Have Known and Loved. Berkeley, CA USA: Transform Press. pp. 403–406. ISBN   0-9630096-9-9.
  2. Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). European Neuropsychopharmacology. 26 (8): 1327–37. doi:10.1016/j.euroneuro.2016.05.001. PMID   27216487. S2CID   6685927.
  3. "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Drug Enforcement Administration (DEA). U.S. Department Of Justice. Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  4. "Placement of 4-hydroxy-N,N-diisopropyltryptamine (4-OH-DiPT), 5-methoxy-alpha-methyltryptamine (5-MeO-AMT), 5-methoxy-N-methyl-N-isopropyltryptamine (5-MeO-MiPT), 5-methoxy-N,N-diethyltryptamine (5-MeO-DET), and N,N-diisopropyltryptamine (DiPT) in Schedule I; Withdrawal of Proposed Rule". 27 July 2022.{{cite web}}: CS1 maint: url-status (link)
  5. "Chapter 893 - Drug Abuse Prevention and Control". Florida Statutes.
  6. "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 15 May 2019.