5-MeO-DPT

Last updated

5-MeO-DPT
5-MeO-DPT.svg
5-MeO-DPT.png
Clinical data
Other names5-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
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of action 12 minutes–<1 hour [1]
Duration of action 2–4 hours [1]
Identifiers
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
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)
  • CCCN(CCC)CCc2c[nH]c1ccc(cc12)OC
  • InChI=1S/C17H26N2O/c1-4-9-19(10-5-2)11-8-14-13-18-17-7-6-15(20-3)12-16(14)17/h6-7,12-13,18H,4-5,8-11H2,1-3H3 Yes check.svgY
  • Key:PNHPVNBKLQWBKH-UHFFFAOYSA-N Yes check.svgY
   (verify)

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]

Contents

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
TargetAffinity (Ki, nM)
5-HT1A 4–149 (Ki)
5–476 (EC50 Tooltip half-maximal effective concentration)
43–95% (Emax Tooltip maximal efficacy)
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 Tooltip Serotonin transporter1,031–1,070 (Ki)
910 ( IC50 )
NET Tooltip Norepinephrine transporter>10,000 (IC50)
DAT Tooltip Dopamine transporter16,998 (IC50)
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes:a = Stimulation of IP1 Tooltip inositol phosphate 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

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. [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

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]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. 1 2 https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2010
  7. ↑ 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.
  8. 1 2 3 4 5 6 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
  9. 1 2 3 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.
  10. 1 2 3 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.
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ 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.
  15. ↑ 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.
  16. ↑ "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). U.S. Department of Justice. February 2023. Retrieved 5 March 2023.
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