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Dipropyltryptamine

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Dipropyltryptamine
Clinical data
Other namesDPT; N,N-Dipropyltryptamine
Routes of
administration		Ingestion, inhalation, intravenous or intramuscular injection
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
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. Use as a designer drug has been documented by law enforcement officials since as early as 1968.[1] However, potential therapeutic use was not investigated until the 1970s.[2] 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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A dose range of DPT of 30 to 70 mg intramuscuarly has been described.[3]

While dipropyltryptamine is chemically similar to dimethyltryptamine (DMT), its psychoactive effects are markedly different.[4]

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,[5] 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: [6][7][8][9][10][11][12]

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.[13]

DPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[3]

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.[14]

History

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DPT was first described in the scientific literature by 1959.[15][16][17]

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.[18]

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Sweden

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DPT is illegal in Sweden as of 26 January 2016.[19]

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,[20] 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.[21]

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. ^ "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.
  2. ^ 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.
  3. ^ 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. [...]
  4. ^ Pinchbeck D (2003). Breaking Open The Head. Broadway Books. ISBN 0-7679-0743-4.
  5. ^ Dupuy B (1 October 2015). "Carver County teen's death puts spotlight on ease of purchasing synthetic drugs online". Star Tribune.
  6. ^ 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.
  7. ^ "PDSP Database". UNC (in Zulu). Retrieved 11 December 2024.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ Spratley T (2004). "Analytical Profiles for Five "Designer" Tryptamines" (PDF). Microgram Journal. 3 (1–2): 55. Retrieved 9 October 2013.
  15. ^ 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.
  16. ^ 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.
  17. ^ 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.
  18. ^ "Temple of the True Inner Light". tripod.com.
  19. ^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
  20. ^ "SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." CFR. Archived from the original on 27 August 2009. Retrieved 17 December 2014.
  21. ^ Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL
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