Dipropyltryptamine

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.

DPT HCl Powder

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
IUPAC name
  • 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)
SMILES
  • CCCN(CCC)CCC1=CNC2=C1C=CC=C2
InChI
  • 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 Y
  • Key:BOOQTIHIKDDPRW-UHFFFAOYSA-N Y
  (verify)

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

Pharmacology

Studies on rodents have found that the effectiveness with which a selective 5-HT2A receptor antagonist blocks the behavioral actions of this compound strongly suggest 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.[3]

Chemistry

DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.[4]

Psychedelic properties

While dipropyltryptamine is chemically similar to [dimethyltryptamine-en] (DMT), its psychoactive effects are markedly different.[5]

Side effects

Negative side effects of human consumption of this drug can include increased heart rate, dizziness, anxiety, confusion, paranoia, seizure and nausea. The use of dipropyltryptamine has been implicated in at least one death as a result of seizures.[6]

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.[7]

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,[8] 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.[9]

Maine

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

Sweden

DPT is illegal in Sweden as of 26 January 2016.[10]

References
  1. "Microgram Journal Volume One No. 7" (PDF). Microgram Journal. U.S DOJ, Bureau of Narcotics and Dangerous Drugs. One (Seven): 23. April 1968 [1968]. Retrieved 5 April 2021.{{cite journal}}: CS1 maint: url-status (link)
  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. 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.
  4. Spratley T (2004). "Analytical Profiles for Five "Designer" Tryptamines" (PDF). Microgram Journal. 3 (1–2): 55. Retrieved 9 October 2013.
  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. "Temple of the True Inner Light". tripod.com.
  8. "SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." CFR. Archived from the original on 27 August 2009. Retrieved 17 December 2014.
  9. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
  10. "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
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