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Dipropyltryptamine

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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
  • N-[2-(1H-indol-3-yl)]ethyl-N-propylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
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)
  • CCCN(CCC)CCC1=CNC2=C1C=CC=C2
  • InChI=1S/C16H24N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h5-8,13,17H,3-4,9-12H2,1-2H3 checkY
  • Key:BOOQTIHIKDDPRW-UHFFFAOYSA-N checkY
  (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 and diethyltryptamine.

Use and effects

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Doses 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 markedly different.[5] On the other hand, others have reported similarities to DMT, for instance in terms of intensity.[1]

Side effects

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Side effects of DET may include nausea, numbness of the tongue or throat, pupil dilation, increased heart rate, dizziness, anxiety, panic, confusion, paranoia, delusions, and seizures (uncommon).[citation needed]

The use of DPT has been implicated in at least one death due to seizures,[6] although details are lacking and the drug has not officially been established as the sole cause of death.

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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DPT activities
Target Affinity (Ki, nM) Species
5-HT1A 31.8–1,641 (Ki)
274–>10,000 (EC50Tooltip half-maximal effective concentration)
99% (EmaxTooltip maximal efficacy)		 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
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
SERTTooltip Serotonin transporter 157 (Ki)
157–23,000 (IC50Tooltip half-maximal inhibitory concentration)
>100,000 (EC50)		 Human
Human
Rat
NETTooltip Norepinephrine transporter >10,000 (Ki)
2,900–3,202 (IC50)
>100,000 (EC50)		 Human
Human
Rat
DATTooltip Dopamine transporter 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: [7][8][9][10][11][12][13]

Studies on rodents have found that the effectiveness with which a selective 5-HT2A receptor antagonist blocks the behavioral actions of this compound strongly suggests that the 5-HT2A receptor is an important site of action for DPT, but the modulatory actions of a 5-HT1A receptor antagonist also imply a 5-HT1A-mediated component to the actions of DPT.[14]

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

Chemistry

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DPT HCl Powder
DPT HCl Powder

DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.[15]

History

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DPT was first described in the scientific literature by 1959.[16][17][18]

Society and culture

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Religious use

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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.[19]

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Sweden

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DPT is illegal in Sweden as of 26 January 2016.[20]

United Kingdom

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

United States

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DPT is not scheduled at the federal level in the United States,[21] 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
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"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.[22]

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

References

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  1. ^ a b c d e f g Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  2. ^ "Microgram Journal Volume One No. 7" (PDF). Microgram Journal. One (Seven). U.S DOJ, Bureau of Narcotics and Dangerous Drugs: 23. April 1968 [1968]. Retrieved 5 April 2021.
  3. ^ Grof S, Soskin RA, Richards WA, Kurland AA (1973). "DPT as an adjunct in psychotherapy of alcoholics". International Pharmacopsychiatry. 8 (1): 104–15. doi:10.1159/000467979. PMID 4150711.
  4. ^ a b 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. Table 4 Human potency data for selected hallucinogens. [...]
  5. ^ Pinchbeck D (2003). Breaking Open The Head. Broadway Books. ISBN 0-7679-0743-4.
  6. ^ Dupuy B (1 October 2015). "Carver County teen's death puts spotlight on ease of purchasing synthetic drugs online". Star Tribune.
  7. ^ Liu, Tiqing (1993). "BindingDB BDBM84934 N-dipropyltryptamine, 1-Isopropyl-5-hydroxy N::N-dipropyltryptamine, 5-Hydroxy-N". The Journal of Pharmacology and Experimental Therapeutics. 265 (3): 1272–1279. PMID 8510008. Retrieved 11 December 2024.
  8. ^ "PDSP Database". UNC (in Zulu). Retrieved 11 December 2024.
  9. ^ 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.
  10. ^ Tyagi R, Saraf TS, Canal CE (October 2023). "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 Pharmacol Transl Sci. 6 (10): 1480–1491. doi:10.1021/acsptsci.3c00137. PMC 10580393. PMID 37854624.
  11. ^ Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter" (PDF). J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
  12. ^ Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.
  13. ^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  14. ^ Fantegrossi WE, Reissig CJ, Katz EB, Yarosh HL, Rice KC, Winter JC (January 2008). "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): 358–65. doi:10.1016/j.pbb.2007.09.007. PMC 2322878. PMID 17905422.
  15. ^ Spratley T (2004). "Analytical Profiles for Five "Designer" Tryptamines" (PDF). Microgram Journal. 3 (1–2): 55. Retrieved 9 October 2013.
  16. ^ Barlow RB, Khan I (December 1959). "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". Br J Pharmacol Chemother. 14 (4): 553–8. doi:10.1111/j.1476-5381.1959.tb00963.x. PMC 1481908. PMID 13796840.
  17. ^ Barlow RB, Khan I (June 1959). "Actions of some analogues of 5-hydroxytryptamine on the isolated rat uterus and the rat fundus strip preparations". Br J Pharmacol Chemother. 14 (2): 265–272. doi:10.1111/j.1476-5381.1959.tb01397.x. PMC 1481803. PMID 13662587.
  18. ^ Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". Br J Pharmacol Chemother. 14 (1): 87–98. doi:10.1111/j.1476-5381.1959.tb00933.x. PMC 1481817. PMID 13651584.
  19. ^ "Temple of the True Inner Light". tripod.com.
  20. ^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
  21. ^ "SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." CFR. Archived from the original on 27 August 2009. Retrieved 17 December 2014.
  22. ^ Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL
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