Dipropyltryptamine

Last updated

Dipropyltryptamine
DPT.svg
DPT-3d-sticks.png
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
Formula C16H24N2
Molar mass 244.382 g·mol−1
3D model (JSmol)
Melting point 174.5 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 Yes check.svgY
  • Key:BOOQTIHIKDDPRW-UHFFFAOYSA-N Yes check.svgY
   (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.

Contents

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

Pharmacology

DPT activities
Target Affinity (Ki, nM)Species
5-HT1A 31.8–1,641 (Ki)
2,430–>10,000 (EC50 Tooltip half-maximal effective concentration)		Human
Human
5-HT1B 854–8,081 (Ki)
1,210 (EC50)		Human
Human
5-HT1D 619Human
5-HT1E 2,338Human
5-HT2A 3.0–2,579 (Ki)
26.1–451 (EC50)
97% (Emax Tooltip maximal efficacy)		Human
Human
Human
5-HT2B 42Human
5-HT2C 281–3,500Human
5-HT3 >10,000Human
5-HT4 NDND
5-HT5A 4,373Human
5-HT6 4,543Human
5-HT7 284Human
D1 >10,000Human
D2 9,249Human
D3 1,361Human
D4 2,014Human
D5 >10,000Human
α1A 881Human
α1B 443Human
α1D NDND
α2A 458Human
α2B 339Human
α2C 514Human
β1–β2 >10,000Human
H1 125Human
H2–H4 >10,000Human
M1–M5 >10,000Human
I1 340Human
σ1 397Human
σ2 2,917Human
SERT Tooltip Serotonin transporter157 (Ki)
157–23,000 (IC50 Tooltip half-maximal inhibitory concentration)
>100,000 (EC50)		Human
Human
Rat
NET Tooltip Norepinephrine transporter>10,000 (Ki)
2,900–3,202 (IC50)
>100,000 (EC50)		Human
Human
Rat
DAT Tooltip Dopamine transporter1,500 (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

DPT HCl Powder N,N-Dipropyltryptamine.jpg
DPT HCl Powder

DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow. [10]

Psychedelic properties

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

Side effects

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.

Interactions

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. [13]

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, [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

"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

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. [16]

References

  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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