Chemistry:5-MeO-DPT

From HandWiki

5-MeO-DPT, also known as 5-methoxy-N,N-dipropyltryptamine, as well as O-methyl-N,N-dipropylserotonin (O-Me-DiPS), is a psychedelic drug of the tryptamine family related to 5-MeO-DMT.[1][2][3][4][5] It is taken orally.[1] The drug has been encountered as a novel designer drug.[6]

Use and effects

Alexander Shulgin included 5-MeO-DPT in a subsection in the 5-MeO-DET entry of his book TiHKAL (Tryptamines I Have Known and Loved).[1] He did not explicitly provide a dose range or duration for 5-MeO-DPT, but did report having tried it at doses of 4 to 8.4 mg orally, with 4 mg producing only threshold effects and doses of 6 to 8.4 mg being more meaningfully active.[1] In a subsequent literature review however, Shulgin gave an explicitly defined dose range of 6 to 10 mg orally.[7] Its onset was described as being 12 minutes to within 1 hour and its duration was 2 to 4 hours.[1]

According to Shulgin, 5-MeO-DPT's actions are ambiguous and not totally positive.[1] This led to him tucking discussion of the drug away in the 5-MeO-DET entry of TiHKAL as opposed to giving 5-MeO-DPT its own entry in the book.[1] The effects of 5-MeO-DPT were only vaguely described.[1] The 4 mg dose produced only threshold effects described as "something".[1] At the 6 mg dose, the effects included possible eroticism, not too much lightheadedness, and comfortableness, with a plus-two rating on the Shulgin Rating Scale.[1][8] On the other hand, at the 8.4 mg dose, there were 5-MeO-DMT-like "head noises" or "bells" described as "bad" and an underlying 5-MeO-DMT-like "turn on" described as "good".[1][8] However, per Shulgin, while these effects alternated, the unpleasant negative effects overall outweighed the positive and desired effects.[1][8] There were no apparent cardiovascular effects at this dose.[1] Shulgin stated that he had "better things to do with my time" and did not further explore 5-MeO-DPT or evaluate higher doses.[1]

5-MeO-DPT's lower homologue 5-MeO-DET was found to produce unique and strong side effects such as lightheadedness, dizziness, and vertigo at low doses which precluded it from being tolerated or used at hallucinogenic doses.[1] Shulgin synthesized and tested 5-MeO-DPT in the hopes that the vertigo-related side effects of 5-MeO-DET would be reduced or eliminated while the hallucinogenic and other desired effects such as sexual enhancement would be preserved.[1] However, while 5-MeO-DET-like side effects were not described, Shulgin nonetheless deemed 5-MeO-DPT an unpromising compound.[1]

Interactions

Pharmacology

Pharmacodynamics

5-MeO-DPT activities
Target Affinity (Ki, nM)
5-HT1A 4–149 (Ki)
2.7–476 (EC50)
43–106% (Emax)
5-HT1B 1,800–>10,000
5-HT1D 99
5-HT1E >10,000
5-HT2A 7–655 (Ki)
6–684a (EC50)
81a–101% (Emax)
5-HT2B 33 (Ki)
14–29 (EC50)
93–98% (Emax)
5-HT2C 1,086–1,290 (Ki)
810a–1,799 (EC50)
81–112% (Emax)
5-HT3 >10,000
5-HT5A >10,000
5-HT6 427
5-HT7 84
KOR 1,211
σ1 279
σ2 491
SERT 1,031–1,284 (Ki)
910 (IC50)
NET >10,000 (IC50)
DAT 16,998 (IC50)

5-MeO-DPT is a potent and high-efficacy agonist of the serotonin 5-HT2A and 5-HT1A receptors.[8][9][10][11] Additionally, the drug has been found to act as a weak serotonin reuptake inhibitor and serotonin 5-HT2C receptor agonist with lower potency.[8][10]

The drug fully substitutes for the serotonin 5-HT2 receptor agonist and serotonergic psychedelic DOM in rodent drug discrimination tests and partially substitutes for the serotonin 5-HT1A receptor agonist 8-OH-DPAT in these tests followed by behavioral disruption at higher doses.[9] 5-MeO-DPT also substitutes for 5-MeO-DMT in rodent drug discrimination tests.[12]

Chemistry

Synthesis

The chemical synthesis of 5-MeO-DPT has been described.[1]

Analogues

Analogues of 5-MeO-DPT include dipropyltryptamine (DPT), 4-HO-DPT (deprocin), 4-AcO-DPT (depracetin), 5-HO-DPT, 5-MeO-DMT, 5-MeO-DET, 5-MeO-DALT, 5-MeO-DBT, 5-MeO-DiPT, 5-MeO-MPT, and 5-MeO-EPT, among others.[1]

History

5-MeO-DPT was first described in the scientific literature by Richard Glennon and colleagues by 1979.[13][14] It was described in greater detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a novel designer drug in Europe in 2010.[6]

Society and culture

Canada

5-MeO-DPT is not a controlled substance in Canada as of 2025.[15]

United States

In the United States, 5-MeO-DPT is considered a Schedule I controlled substance as a positional isomer of 5-MeO-DiPT.[16][17]

See also

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 1.14 1.15 1.16 1.17 1.18 1.19 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  2. ↑ "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities". Psychopharmacology 68 (2): 155–8. 1980. doi:10.1007/BF00432133. PMID 6776558. 
  3. ↑ "Identification and quantitative determination of 5-methoxy-N, N-di-n-propyltryptamine in urine by isotope dilution gas chromatography-mass spectrometry.". Forensic Toxicology 25 (1): 1–7. June 2007. doi:10.1007/s11419-006-0018-y. 
  4. ↑ "Simultaneous determination of tryptamine analogues in designer drugs using gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry.". Forensic Toxicology 32 (1): 154–61. January 2014. doi:10.1007/s11419-013-0208-3. 
  5. ↑ "5-Meth-oxy-N,N-di-n-propyl-tryptamine (5-MeO-DPT): freebase and fumarate". Acta Crystallographica Section E 77 (Pt 5): 522–526. May 2021. doi:10.1107/S2056989021003753. PMID 34026257. Bibcode: 2021AcCrE..77..522P. 
  6. ↑ 6.0 6.1 https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2010
  7. ↑ "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. 
  8. ↑ 8.0 8.1 8.2 8.3 8.4 "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl) 231 (21): 4135–4144. October 2014. doi:10.1007/s00213-014-3557-7. PMID 24800892. "[5-MeO-DPT:] Comfortable at low doses, oscillating good and bad sounds, negative side dominated as buzz continues". 
  9. ↑ 9.0 9.1 Cite error: Invalid <ref> tag; no text was provided for refs named GlennonTitelerLyon1988
  10. ↑ 10.0 10.1 Cite error: Invalid <ref> tag; no text was provided for refs named KozellEshlemanSwanson2023
  11. ↑ "Structural pharmacology and therapeutic potential of 5-methoxytryptamines". Nature 630 (8015): 237–246. June 2024. doi:10.1038/s41586-024-07403-2. PMID 38720072. 
  12. ↑ "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities". Psychopharmacology (Berl) 68 (2): 155–158. 1980. doi:10.1007/BF00432133. PMID 6776558. 
  13. ↑ "Serotonin receptor binding affinities of tryptamine analogues". J Med Chem 22 (4): 428–432. April 1979. doi:10.1021/jm00190a014. PMID 430481. 
  14. ↑ "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neurosci Biobehav Rev 6 (4): 489–497. 1982. doi:10.1016/0149-7634(82)90030-6. PMID 6757811. 
  15. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  16. ↑ "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals". U.S. Department of Justice. February 2023. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf. 
  17. ↑ Drug Enforcement Administration (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances". https://www.federalregister.gov/documents/2007/12/03/E7-23413/definition-of-positional-isomer-as-it-pertains-to-the-control-of-schedule-i-controlled-substances. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:5-MeO-DPT&oldid=4246336"