5-MeO-DPT
Psychedelic drug
From Wikipedia, the free encyclopedia
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]
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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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| Formula | C17H26N2O |
| Molar mass | 274.408 g·mol−1 |
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| Melting point | 193 to 194 °C (379 to 381 °F) |
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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
| 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) |
| 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
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
Legal status
Canada
5-MeO-DPT is not a controlled substance in Canada as of 2025.[16]
United States
In the United States, 5-MeO-DPT is considered a Schedule I controlled substance as a positional isomer of 5-MeO-DiPT.[17][18]