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5-MeO-DPT
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| Clinical data | |
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| Other names | 5-Methoxy-N,N-dipropyltryptamine; O-Methyl-N,N-dipropylserotonin; O-Me-DiPS |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor modulator; Serotonin 5-HT1A receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Pharmacokinetic data | |
| Onset of action | 12 minutes–<1 hour[1] |
| Duration of action | 2–4 hours[1] |
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| Chemical and physical data | |
| Formula | C17H26N2O |
| Molar mass | 274.408 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 193 to 194 °C (379 to 381 °F) |
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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
[edit]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
[edit]Pharmacology
[edit]Pharmacodynamics
[edit]| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 4–149 (Ki) 5–476 (EC50) 43–95% (Emax) |
| 5-HT1B | 1,800–>10,000 |
| 5-HT2A | 7–655 (Ki) 6–684a (EC50) 81a–101% (Emax) |
| 5-HT2B | 33 |
| 5-HT2C | 1,086–1,290 (Ki) 810a (EC50) 96%a (Emax) |
| 5-HT3 | >10,000 |
| 5-HT5A | >10,000 |
| 5-HT6 | 427 |
| 5-HT7 | 84 |
| KOR | 1,211 |
| SERT | 1,031–1,070 (Ki) 910 (IC50) |
| NET | >10,000 (IC50) |
| DAT | 16,998 (IC50) |
| Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes: a = Stimulation of IP1 formation. Sources: [8][9][10] [11] | |
5-MeO-DPT is a potent and high-efficacy agonist of the serotonin 5-HT2A and 5-HT1A receptors.[8][9][10][12] 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.[13]
Chemistry
[edit]Synthesis
[edit]The chemical synthesis of 5-MeO-DPT has been described.[1]
Analogues
[edit]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
[edit]5-MeO-DPT was first described in the scientific literature by Richard Glennon and colleagues by 1979.[14][15] 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
[edit]Legal status
[edit]United States
[edit]In the United States, 5-MeO-DPT is considered a Schedule I controlled substance as a positional isomer of 5-MeO-DiPT.[16]
See also
[edit]References
[edit]- ^ a b c d e f g h i j k l m n o p q r s t u v w Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
- ^ Glennon RA, Young R, Rosecrans JA, Kallman MJ (1980). "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities". Psychopharmacology. 68 (2): 155–8. doi:10.1007/BF00432133. PMID 6776558. S2CID 1674481.
- ^ Nakamoto A, Namera A, Nishida M, Yashiki M, Kuramoto T, Kimura K (June 2007). "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. doi:10.1007/s11419-006-0018-y. S2CID 9906203.
- ^ Nakazono Y, Tsujikawa K, Kuwayama K, Kanamori T, Iwata YT, Miyamoto K, Kasuya F, Inoue H (January 2014). "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. doi:10.1007/s11419-013-0208-3. S2CID 25134125.
- ^ Pham DN, Chadeayne AR, Golen JA, Manke DR (May 2021). "5-Meth-oxy-N,N-di-n-propyl-tryptamine (5-MeO-DPT): freebase and fumarate". Acta Crystallographica Section E. 77 (Pt 5): 522–526. Bibcode:2021AcCrE..77..522P. doi:10.1107/S2056989021003753. PMC 8100262. PMID 34026257.
- ^ a b https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2010
- ^ Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
- ^ a b c d e f 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.
[5-MeO-DPT:] Comfortable at low doses, oscillating good and bad sounds, negative side dominated as buzz continues
- ^ a b c Glennon RA, Titeler M, Lyon RA, Slusher RM (April 1988). "N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin". J Med Chem. 31 (4): 867–870. doi:10.1021/jm00399a031. PMID 2965244.
- ^ a b c 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". J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
- ^ Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID 39636099.
- ^ Warren AL, Lankri D, Cunningham MJ, Serrano IC, Parise LF, Kruegel AC, Duggan P, Zilberg G, Capper MJ, Havel V, Russo SJ, Sames D, Wacker D (June 2024). "Structural pharmacology and therapeutic potential of 5-methoxytryptamines". Nature. 630 (8015): 237–246. doi:10.1038/s41586-024-07403-2. PMC 11152992. PMID 38720072.
- ^ Glennon RA, Young R, Rosecrans JA, Kallman MJ (1980). "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities". Psychopharmacology (Berl). 68 (2): 155–158. doi:10.1007/BF00432133. PMID 6776558.
- ^ Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues". J Med Chem. 22 (4): 428–432. doi:10.1021/jm00190a014. PMID 430481.
- ^ Glennon RA, Rosecrans JA (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neurosci Biobehav Rev. 6 (4): 489–497. doi:10.1016/0149-7634(82)90030-6. PMID 6757811.
- ^ "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). U.S. Department of Justice. February 2023. Retrieved 5 March 2023.