DiPT

Last updated
DiPT
DiPT.svg
DiPT-3d-sticks.png
Clinical data
Pronunciation /ˌdaɪˌaɪsoʊˌproʊpɪlˈtrɪptəmiːn/
Other namesDiisopropyltryptamine; N,N-Diisopropyltryptamine; DiPT; DIPT; Dipt; Dipsy
Routes of
administration 		Oral [1]
Drug class Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • AU:Unscheduled
  • CA:Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US:Unscheduled
  • UN:Unscheduled
Pharmacokinetic data
Duration of action 6–8 hours [1]
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 (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 aural. [1]

Contents

Dosage

Alexander Shulgin in TiHKAL gave a dosage range of DiPT of 25 to 100 mg orally and a duration of 6 to 8 hours. [1] A wider recreational dose range for DiPT of 15 to 150 mg or more has also been reported. [2]

Effects

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]

Interactions

Pharmacology

Pharmacodynamics

DiPT activities
Target Affinity (Ki, nM)
5-HT1A 121–538
5-HT1B >10,000
5-HT1D 3,742
5-HT1E >10,000
5-HT1F ND
5-HT2A 1,200–>10,000 (Ki)
240–1,411 (EC50 Tooltip half-maximal effective concentration)
89–117% (Emax Tooltip maximal efficacy)
5-HT2B 399 (Ki)
1,000–2,380 (EC50)
103–107% (Emax)
5-HT2C 290–>10,000 (Ki)
167–1,999 (EC50)
81–143% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 >10,000
5-HT7 3,423
α1A >12,000
α1B >10,000
α1D ND
α2A 3,600–>10,000
α2B 2,870
α2C 2,523
β1 >10,000
β2 >10,000
β3 ND
D1 >25,000
D2 >25,000
D3 3,321–>25,000
D4 >10,000
D5 >10,000
H1 920–3,583
H2 >10,000
H3 ND
H4 >10,000
M1 >10,000
M2 >10,000
M3 >10,000
M4 >10,000
M5 >10,000
I1 356
σ1 1,798
σ2 2,702
TAAR1 Tooltip Trace amine-associated receptor 1>15,000 (Ki) (mouse)
>15,000 (Ki) (rat)
ND (EC50) (mouse)
ND (EC50) (rat)
ND (EC50) (human)
ND (Emax) (mouse)
ND (Emax) (rat)
SERT Tooltip Serotonin transporter180–1,258 (Ki)
900 (IC50 Tooltip half-maximal inhibitory concentration)
IA (EC50)
NET Tooltip Norepinephrine transporter8,900–>10,000 (Ki)
9,900 (IC50)
IA (EC50)
DAT Tooltip Dopamine transporter4,100–>10,000 (Ki)
35,000 (IC50)
IA (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [3] [4] [5] [6] [7]

DiPT binds to serotonin receptors including the serotonin 5-HT1A, 5-HT2A, 5-HT2B, 5-HT2C receptors among others. [4] [5] It is known to act as a full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [4] [5] It is also a weak serotonin reuptake inhibitor. [5] In contrast to many related drugs, DiPT does not interact with the rodent or human trace amine-associated receptor 1 (TAAR1). [7]

The discriminative stimulus properties of DiPT in rodent drug discrimination tests are partially blocked by the serotonin 5-HT2A receptor antagonist volinanserin and by the serotonin 5-HT2C receptor antagonist SB-242084. [6] This is in contrast to the case of the related psychedelic dimethyltryptamine (DMT), wherein volinanserin fully blocks its stimulus properties and SB-242084 has minimal influence. [6] Similarly to DMT and other psychedelics, DiPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents, and this effect is blocked by volinanserin. [6] [8]

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.

Analogues of DiPT include dimethyltryptamine (DMT), diethyltryptamine (DET), dipropyltryptamine (DPT), 5-MeO-DMT, 5-MeO-DPT, 5-MeO-AMT, 5-MeO-DiPT, 4-HO-DiPT (iprocin), 5-HO-DiPT, 4-AcO-DiPT (ipracetin), and 5,6-MDO-DiPT, among others.

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, [9] 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. [10]

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. [11]

Sweden

Sweden's public health agency suggested classifying DiPT as a hazardous substance, on May 15, 2019. [12]

References

  1. 1 2 3 4 5 6 7 Shulgin A (1997). TiHKAL: Tryptamines I Have Known and Loved. Berkeley, CA USA: Transform Press. pp. 403–406. ISBN   0-9630096-9-9.
  2. ↑ Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC   6165951 . PMID   29850881.
  3. ↑ "Kᵢ Database". PDSP. 25 March 2025. Retrieved 25 March 2025.
  4. 1 2 3 Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi: 10.1371/journal.pone.0009019 . PMC   2814854 . PMID   20126400.
  5. 1 2 3 4 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): 1327–1237. doi:10.1016/j.euroneuro.2016.05.001. PMID   27216487. S2CID   6685927.
  6. 1 2 3 4 Carbonaro TM, Eshleman AJ, Forster MJ, Cheng K, Rice KC, Gatch MB (January 2015). "The role of 5-HT2A, 5-HT 2C and mGlu2 receptors in the behavioral effects of tryptamine hallucinogens N,N-dimethyltryptamine and N,N-diisopropyltryptamine in rats and mice". Psychopharmacology (Berl). 232 (1): 275–284. doi:10.1007/s00213-014-3658-3. PMC   4282596 . PMID   24985890. DiPT bound with moderate affinity to the 5-HT2C receptor (Ki= 290 ± 110 nM; Hill coefficient = −0.72 ± 0.05) and was a full agonist in the IP-1 formation assay (EC50 = 2380 ± 340 nM), producing 107.4 ± 2.5% of the maximal 5-HT effect.
  7. 1 2 Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID   26791601.
  8. ↑ Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167: 107933. doi:10.1016/j.neuropharm.2019.107933. PMC   9191653 . PMID   31917152.
  9. ↑ "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.
  10. ↑ "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.
  11. ↑ "Chapter 893 - Drug Abuse Prevention and Control". Florida Statutes.
  12. ↑ "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 15 May 2019. Archived from the original on 20 October 2021. Retrieved 11 November 2019.
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