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5-MeO-DPT
Psychedelic drug
Psychedelic drug
| Field | Value | |||
|---|---|---|---|---|
| Verifiedfields | verified | |||
| Watchedfields | verified | |||
| verifiedrevid | 477224958 | |||
| image | 5-MeO-DPT.svg | |||
| image_class | skin-invert-image | |||
| width | 220px | |||
| image2 | 5-MeO-DPT.png | |||
| image_class2 | bg-transparent | |||
| width2 | 220px | |||
| routes_of_administration | Oral | |||
| class | Serotonin receptor modulator; Serotonin [5-HT1A receptor](5-ht1a-receptor) agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen | |||
| ATC_prefix | None | |||
| legal_DE | NpSG | |||
| legal_UK | Class A | |||
| legal_US | Schedule I (isomer of 5-MeO-DIPT) | |||
| onset | 12 minutes– | |||
| duration_of_action | 2–4 hours | |||
| CAS_number_Ref | ||||
| CAS_number | 69496-75-9 | |||
| PubChem | 14011047 | |||
| ChemSpiderID_Ref | ||||
| ChemSpiderID | 14106484 | |||
| ChEMBL_Ref | ||||
| ChEMBL | 169328 | |||
| UNII_Ref | ||||
| UNII | AYW60P516B | |||
| synonyms | 5-Methoxy-*N*,*N*-dipropyltryptamine; *O*-Methyl-*N*,*N*-dipropylserotonin; *O*-Me-DiPS | |||
| IUPAC_name | *N*-[2-(5-methoxy-1*H*-indol-3-yl)ethyl]-*N*-propylpropan-1-amine | |||
| C | 17 | H=26 | N=2 | O=1 |
| SMILES | CCCN(CCC)CCc2c[nH]c1ccc(cc12)OC | |||
| StdInChI_Ref | ||||
| StdInChI | 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 | |||
| StdInChIKey_Ref | ||||
| StdInChIKey | PNHPVNBKLQWBKH-UHFFFAOYSA-N | |||
| melting_point | 193 | |||
| melting_high | 194 |
| elimination_half-life =
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. It is taken orally. The drug has been encountered as a novel designer drug.
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). 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 8.4mg orally, with 4mg producing only threshold effects and doses of 6 to 8.4mg being more meaningfully active. In a subsequent literature review however, Shulgin gave an explicitly defined dose range of 6 to 10mg orally. Its onset was described as being 12minutes to within 1hour and its duration was 2 to 4hours.
According to Shulgin, 5-MeO-DPT's actions are ambiguous and not totally positive. 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. The effects of 5-MeO-DPT were only vaguely described. The 4mg dose produced only threshold effects described as "something". At the 6mg dose, the effects included possible eroticism, not too much lightheadedness, and comfortableness, with a plus-two rating on the Shulgin Rating Scale. On the other hand, at the 8.4mg 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". However, per Shulgin, while these effects alternated, the unpleasant negative effects overall outweighed the positive and desired effects. There were no apparent cardiovascular effects at this dose. Shulgin stated that he had "better things to do with my time" and did not further explore 5-MeO-DPT or evaluate higher doses.
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. 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. However, while 5-MeO-DET-like side effects were not described, Shulgin nonetheless deemed 5-MeO-DPT an unpromising compound.
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| [5-HT1A](5-ht1a-receptor) | 4–149 (Ki) |
| 2.7–476 () | |
| 43–106% () | |
| [5-HT1B](5-ht1b-receptor) | 1,800–10,000 |
| [5-HT1D](5-ht1d-receptor) | 99 |
| [5-HT1E](5-ht1e-receptor) | 10,000 |
| [5-HT2A](5-ht2a-receptor) | 7–655 (Ki) |
| 6–684a (EC50) | |
| 81a–101% (Emax) | |
| [5-HT2B](5-ht2b-receptor) | 33 (Ki) |
| 14–29 (EC50) | |
| 93–98% (Emax) | |
| [5-HT2C](5-ht2c-receptor) | 1,086–1,290 (Ki) |
| 810a–1,799 (EC50) | |
| 81–112% (Emax) | |
| [5-HT3](5-ht3-receptor) | 10,000 |
| [5-HT5A](5-ht5a-receptor) | 10,000 |
| [5-HT6](5-ht6-receptor) | 427 |
| [5-HT7](5-ht7-receptor) | 84 |
| KOR | 1,211 |
| σ1 | 279 |
| σ2 | 491 |
| 1,031–1,284 (Ki) | |
| 910 (IC50) | |
| 10,000 (IC50) | |
| 16,998 (IC50) | |
| **Notes:** The smaller the value, the more avidly the drug interacts with the site. **Footnotes:** a = Stimulation of formation. **Sources:** |
5-MeO-DPT is a potent and high-efficacy agonist of the serotonin 5-HT2A and 5-HT1A receptors. Additionally, the drug has been found to act as a weak serotonin reuptake inhibitor and serotonin 5-HT2C receptor agonist with lower potency.
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. 5-MeO-DPT also substitutes for 5-MeO-DMT in rodent drug discrimination tests.
Chemistry
Synthesis
The chemical synthesis of 5-MeO-DPT has been described.
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.
History
5-MeO-DPT was first described in the scientific literature by Richard Glennon and colleagues by 1979. It was described in greater detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). The drug was encountered as a novel designer drug in Europe in 2010.
Society and culture
Legal status
Canada
5-MeO-DPT is not a controlled substance in Canada as of 2025.
United States
In the United States, 5-MeO-DPT is considered a Schedule I controlled substance as a positional isomer of 5-MeO-DiPT.{{cite web |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf|title=Lists of: Scheduling Actions Controlled Substances Regulated Chemicals|publisher=U.S. Department of Justice|date=February 2023 |access-date=5 March 2023}}
References
References
- {{CiteTiHKAL
- (1980). "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities". Psychopharmacology.
- (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.
- (January 2014). "Simultaneous determination of tryptamine analogues in designer drugs using gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry.". Forensic Toxicology.
- (May 2021). "5-Meth-oxy-N,N-di-n-propyl-tryptamine (5-MeO-DPT): freebase and fumarate". Acta Crystallographica Section E.
- (2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
- (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.
- (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.
- (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci.
- (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl).
- (June 2024). "Structural pharmacology and therapeutic potential of 5-methoxytryptamines". Nature.
- (1980). "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities". Psychopharmacology (Berl).
- (April 1979). "Serotonin receptor binding affinities of tryptamine analogues". J Med Chem.
- (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neurosci Biobehav Rev.
- https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2010
- "Controlled Drugs and Substances Act".
- [[Drug Enforcement Administration]]. (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances".
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