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Dipropyltryptamine

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Dipropyltryptamine
Clinical data
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 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.

Frequent physical effects are nausea, numbness of the tongue or throat, and pupil dilation.

Pharmacology

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DPT activities
Target Affinity (Ki, nM) Species
5-HT1A 31.8–1,641 (Ki)
2,430–>10,000 (EC50Tooltip half-maximal effective concentration)		 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)
26.1–451 (EC50)
97% (EmaxTooltip maximal efficacy)		 Human
Human
Human
5-HT2B 42 Human
5-HT2C 281–3,500 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: [3][4][5][6][7][8]

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.[9]

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.[10]

Psychedelic properties

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While dipropyltryptamine is chemically similar to dimethyltryptamine (DMT), its psychoactive effects are markedly different.[11]

Side effects

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Negative side effects of human consumption of this drug may include increased heart rate, dizziness, anxiety, panic, confusion, paranoia, delusions, seizure (uncommon) and nausea. The use of dipropyltryptamine has been implicated in at least one death due to seizures,[12] although details are lacking and the drug has not officially been established as the sole cause of death.

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.[13]

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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,[14] 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.[15]

Maine

[edit]

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

Sweden

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DPT is illegal in Sweden as of 26 January 2016.[16]

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