Chemistry:Dipropyltryptamine

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Short description: Chemical compound

Dipropyltryptamine
Clinical data
Other namesDPT; N,N-Dipropyltryptamine
Routes of
administration		Oral, inhalation (smoking), intravenous or intramuscular injection[1]
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Pharmacokinetic data
Onset of actionInjection: 10–15 minutes[1]
Duration of action2–4 hours[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H24N2
Molar mass244.382 g·mol−1
3D model (JSmol)
Melting point174.5 to 178 °C (346.1 to 352.4 °F)
  (verify)

N,N-Dipropyltryptamine (DPT) is a psychedelic drug and entheogen belonging to the tryptamine family.[1] Use as a designer drug has been documented by law enforcement officials since as early as 1968.[2] However, potential therapeutic use was not investigated until the 1970s.[3] 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 (DMT) and diethyltryptamine (DET).

Use and effects

Dose ranges of DPT of 100 to 250 mg (but up to 500 mg) orally, 100 mg smoked, 15 to 125 mg intramuscularly, and 12 to 36 mg intravenously have been described.[1][4] Its duration is 2 to 4 hours orally but can last up to 12 hours with high doses.[1]

While DPT is chemically similar to dimethyltryptamine (DMT), its psychoactive effects have been said to be qualitatively markedly different.[5] On the other hand, others have reported similarities to DMT, for instance in terms of intensity.[1]

Side effects

Although tryptamines such as psilocybin and dimethyltryptamine (DMT) have relatively well‑characterized safety, synthetic analogues like DPT lack thorough toxicological evaluation and are mainly associated with anecdotal reports of intoxication and a few cases of fatal outcomes when used recreationally.[6] The pharmacological similarity of DPT to DMT suggests a generally low intrinsic toxicity at controlled doses but a pronounced risk of acute adverse reactions, including agitation, tachycardia, hyperthermia, and serotonergic crisis, particularly in combination with monoamine oxidase inhibitors or other serotonergic substances.[6]

A meta-analysis of tryptamine psychedelics have further demonstrated cognitive effects through serotonin 5-HT2A receptor modulation but have not identified persistent neurotoxicity.[7] The main safety concerns are acute psychophysiological and behavioral disturbances rather than long‑term organ toxicity. Overall, DPT is a potent, short‑acting serotonergic hallucinogen with limited safety data and a toxicity profile comparable to related tryptamines such as DMT and 5-MeO-DMT.[6][7]

Interactions

Pharmacology

Pharmacodynamics

DPT activities
Target Affinity (Ki, nM) Species
5-HT1A 31.8–1,641 (Ki)
274–>10,000 (EC50)
99% (Emax)		 Human
Human
Human
5-HT1B 854–8,081 (Ki)
1,210 (EC50)		 Human
Human
5-HT1D 619 Human
5-HT1E 2,338 Human
5-HT2A 3.0–2,579 (Ki)
26.1–943 (EC50)
85–97% (Emax)		 Human
Human
Human
5-HT2B 42 Human
5-HT2C 281–3,500 (Ki)
444 (EC50)
93% (Emax)		 Human
Human
Human
5-HT3 >10,000 Human
5-HT4 ND ND
5-HT5A 4,373 Human
5-HT6 4,543 Human
5-HT7 284 Human
D1 >10,000 Human
D2 9,249 Human
D3 1,361 Human
D4 2,014 Human
D5 >10,000 Human
α1A 881 Human
α1B 443 Human
α1D ND ND
α2A 458 Human
α2B 339 Human
α2C 514 Human
β1–β2 >10,000 Human
H1 125 Human
H2–H4 >10,000 Human
M1–M5 >10,000 Human
I1 340 Human
σ1 397 Human
σ2 2,917 Human
SERT 157 (Ki)
157–23,000 (IC50)
>100,000 (EC50)		 Human
Human
Rat
NET >10,000 (Ki)
2,900–3,202 (IC50)
>100,000 (EC50)		 Human
Human
Rat
DAT 1,500 (Ki)
2,218–9,100 (IC50)
>100,000 (EC50)		 Human
Human
Rat
Notes: The smaller the value, the more avidly the drug binds to the site. Refs: [8][9][10][11][12][13][14]

Studies on rodents have found that the effectiveness with which a selective 5-HT2A receptor antagonist blocks the behavioral actions of DPT strongly suggests that the 5-HT2A receptor is an important site of action for the drug, but the modulatory actions of a serotonin 5-HT1A receptor antagonist also imply a serotonin 5-HT1A receptor-mediated component to the actions of DPT.[15]

DPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[4]

Chemistry

DPT HCl Powder
DPT hydrochloride powder.

Detection

DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.[16]

Analogues

Analogues of DPT include dimethyltryptamine (DMT), diethyltryptamine (DET), diisopropyltryptamine (DiPT), diallyltryptamine (DALT), methylpropyltryptamine (MPT), ethylpropyltryptamine (EPT), propylisopropyltryptamine (PiPT), 4-HO-DPT, 5-HO-DPT, and 5-MeO-DPT, among others.

History

DPT was first described in the scientific literature by 1959.[17][18][19]

Society and culture

Religious use

DPT is used as a religious sacrament by the Temple of the True Inner Light, a New York City offshoot of the Native American Church. The Temple believes DPT and other entheogens are physical manifestations of God.[20]

Sweden

DPT is illegal in Sweden as of 26 January 2016.[21]

United Kingdom

DPT is a Class A drug in the United Kingdom, making it illegal to possess or distribute.

United States

DPT is not scheduled at the federal level in the United States,[22] but it could be considered an analog of 5-MeO-DiPT, DMT, or DET, in which case purchase, sale, or possession could be prosecuted under the Federal Analogue Act.

Florida

"DPT (N,N-Dipropyltryptamine)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[23]

Maine

DPT is a Schedule I controlled substance in the state of Maine making it illegal to buy, sell, or possess in Maine.

Research

Fragile X syndrome

DPT has been found to completely prevent audiogenic seizures in mouse models of fragile X syndrome (FXS) at a 10 mg/kg dose, with its mechanism of action appearing to be independent of serotonin and sigma σ1 receptor activation.[24] While DPT is an agonist at several serotonin receptors in vitro, its anticonvulsant effects were not blocked by selective serotonin 5-HT2A, 5-HT1A, or 5-HT1B receptor antagonists nor by a selective sigma σ1 receptor antagonist in vivo.[24] The drug's beneficial effects may be mediated by non-serotonergic pathways, possibly involving direct auditory processing modulation.[24] At higher doses, DPT switched from anticonvulsant to proconvulsant action, indicating complex interactions.[24]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  2. ↑ "Microgram Journal Volume One No. 7". Microgram Journal (U.S DOJ, Bureau of Narcotics and Dangerous Drugs) One (Seven): 23. April 1968. https://www.erowid.org/library/periodicals/microgram/microgram_1968_04_v01n07.pdf. Retrieved 5 April 2021. 
  3. ↑ "DPT as an adjunct in psychotherapy of alcoholics". International Pharmacopsychiatry 8 (1): 104–115. 1973. doi:10.1159/000467979. PMID 4150711. 
  4. ↑ 4.0 4.1 "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. May 2020. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. PMC 9191653. http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf. "Table 4 Human potency data for selected hallucinogens. [...]". 
  5. ↑ Breaking Open The Head. Broadway Books. 2003. ISBN 978-0-7679-0743-9. 
  6. ↑ 6.0 6.1 6.2 "The hallucinogenic world of tryptamines: an updated review". Archives of Toxicology 89 (8): 1151–1173. August 2015. doi:10.1007/s00204-015-1513-x. PMID 25877327. Bibcode: 2015ArTox..89.1151A. 
  7. ↑ 7.0 7.1 "The Effects of Tryptamine Psychedelics in the Brain: A meta-Analysis of Functional and Review of Molecular Imaging Studies". Frontiers in Pharmacology 12. 2021. doi:10.3389/fphar.2021.739053. PMID 34658876. 
  8. ↑ "Species differences in the pharmacology of the 5-hydroxytryptamine2 receptor: structurally specific differentiation by ergolines and tryptamines". The Journal of Pharmacology and Experimental Therapeutics 265 (3): 1272–1279. June 1993. doi:10.1016/S0022-3565(25)38269-8. PMID 8510008. https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=84934. Retrieved 11 December 2024. 
  9. ↑ "PDSP Database" (in zu). https://pdsp.unc.edu/databases/pdsp.php?testFreeRadio=testFreeRadio&testLigand=dipropyltryptamine&kiAllRadio=all&doQuery=Submit+Query. 
  10. ↑ "Psychedelics and the human receptorome". PLOS ONE 5 (2). February 2010. doi:10.1371/journal.pone.0009019. PMID 20126400. Bibcode: 2010PLoSO...5.9019R. 
  11. ↑ "The Psychedelic N,N-Dipropyltryptamine Prevents Seizures in a Mouse Model of Fragile X Syndrome via a Mechanism that Appears Independent of Serotonin and Sigma1 Receptors". ACS Pharmacology & Translational Science 6 (10): 1480–1491. October 2023. doi:10.1021/acsptsci.3c00137. PMID 37854624. 
  12. ↑ "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". The Journal of Pharmacology and Experimental Therapeutics 385 (1): 62–75. April 2023. doi:10.1124/jpet.122.001454. PMID 36669875. 
  13. ↑ "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology 231 (21): 4135–4144. October 2014. doi:10.1007/s00213-014-3557-7. PMID 24800892. 
  14. ↑ "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology 559 (2–3): 132–137. March 2007. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. 
  15. ↑ "Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents". Pharmacology, Biochemistry, and Behavior 88 (3): 358–365. January 2008. doi:10.1016/j.pbb.2007.09.007. PMID 17905422. 
  16. ↑ "Analytical Profiles for Five "Designer" Tryptamines". Microgram Journal 3 (1–2): 55. 2004. http://www.erowid.org/library/periodicals/microgram/microgram_journal_2005-1.pdf#page=54. Retrieved 2013-10-09. 
  17. ↑ "The use of the guinea-pig ileum preparation for testing the activity of substances which imitate or antagonize the actions of 5-hydroxytryptamine and tryptamine". British Journal of Pharmacology and Chemotherapy 14 (4): 553–558. December 1959. doi:10.1111/j.1476-5381.1959.tb00963.x. PMID 13796840. 
  18. ↑ "Actions of some analogues of 5-hydroxytryptamine on the isolated rat uterus and the rat fundus strip preparations". British Journal of Pharmacology and Chemotherapy 14 (2): 265–272. June 1959. doi:10.1111/j.1476-5381.1959.tb01397.x. PMID 13662587. 
  19. ↑ "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". British Journal of Pharmacology and Chemotherapy 14 (1): 87–98. March 1959. doi:10.1111/j.1476-5381.1959.tb00933.x. PMID 13651584. 
  20. ↑ "Temple of the True Inner Light". tripod.com. http://psychede.tripod.com/. 
  21. ↑ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. November 2015. http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/november/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/. 
  22. ↑ "SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.". CFR. http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm. 
  23. ↑ Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL
  24. ↑ 24.0 24.1 24.2 24.3 "The Psychedelic N,N-Dipropyltryptamine Prevents Seizures in a Mouse Model of Fragile X Syndrome via a Mechanism that Appears Independent of Serotonin and Sigma1 Receptors". ACS Pharmacology & Translational Science 6 (10): 1480–1491. October 2023. doi:10.1021/acsptsci.3c00137. PMID 37854624. 

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