4-MeO-MiPT
Chemical compound
From Wikipedia, the free encyclopedia
4-MeO-MiPT, also known as 4-methoxy-N-methyl-N-isopropyltryptamine, is a lesser-known psychedelic drug of the tryptamine and 4-methoxytryptamine families.[1] It is the 4-methoxy analogue of MiPT and the O-methyl ether of 4-HO-MiPT.[1] The drug is taken orally.[1]
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| Other names | 4-OMe-MiPT; 4-Methoxy-N-methyl-N-isopropyltryptamine |
| Routes of administration | Oral[1] |
| Drug class | Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Serotonin reuptake inhibitor |
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| Onset of action | 20–40 minutes[1] |
| Duration of action | 4–6 hours[1][2] |
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| Chemical and physical data | |
| Formula | C15H22N2O |
| Molar mass | 246.354 g·mol−1 |
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| Melting point | 80 to 81 °C (176 to 178 °F) |
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It acts as a serotonin reuptake inhibitor and as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[3][4] The drug produces psychedelic-like effects in animals.[4]
4-MeO-MiPT was first described by David Repke and Alexander Shulgin and colleagues in 1985.[5] It was subsequently further described by Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known And Loved).[1] The drug was reported as a novel designer drug by 2016.[6][2] Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-MeO-MiPT.[1][3]
Use and effects
Alexander Shulgin found the effective dose of 4-MeO-MiPT to be 20 to 30 mg (or ~0.4 mg/kg body weight of subject) orally; the onset between ingestion and the first noticeable effects was 20 to 40 minutes, with a listed duration of 4 to 6 hours.[1][5][2] The effects were significantly milder than those of 4-HO-MiPT, with 4-MeO-MiPT producing erotic-enhancing effects, and few of the visuals common with tryptamines.[1][2] Online anecdotal reports describe 4-MeO-MiPT as producing mild psychedelic effects with little body load.[2]
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 347–731 (Ki) 1,072–1,490 (EC50) 97–99% (Emax) |
| 5-HT1B | >10,000 |
| 5-HT1D | 441 |
| 5-HT1E | >10,000 |
| 5-HT2A | 178–470 (Ki) 5.6–376a (EC50) 63–90% (Emax) |
| 5-HT2B | 48 (Ki) 16.8–53 (EC50) 66–75% (Emax) |
| 5-HT2C | 510–810 (Ki) 23–120a (EC50) 77–96% (Emax) |
| 5-HT3 | >10,000 |
| 5-HT5A | >10,000 |
| 5-HT6 | 1,004 |
| 5-HT7 | >10,000 |
| α2A | 240 |
| α2B | 1,806 |
| α2C | 552 |
| H1 | >10,000 |
| σ1 | 1,037 |
| σ2 | 843 |
| SERT | 38–41 (Ki) 53–57 (IC50) |
| NET, DAT | >10,000 |
| Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes: a = Stimulation of IP1 formation. Sources: [3][4] | |
4-MeO-MiPT acts as a serotonin reuptake inhibitor (SRI) and non-selective serotonin receptor agonist, including of the serotonin 5-HT1A, 5-HT2A, 5-HT2B, 5-HT2C receptors.[3][4][7] The substance additionally displayed sub micromolar affinities at α2A, α2C and σ2 receptors.[7]
Increased extracellular concentrations of serotonin, resulting from SERT blockade, similarly may compete at the serotonin 5-HT2A receptor, altering or blunting effects mediated by this receptor, which could potentially explain anecdotal reports of subjective effects being dose-dependently milder than that of 4-HO-MiPT or 5-MeO-MiPT.[1][3][7] This profile makes 4-MeO-MiPT a potential candidate for elucidating the role of SERT blockade in the mechanisms underlying serotonergic psychedelic action.[3][4][7]
The drug induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[4][7] Its potency for inducing the head-twitch response in mice is similar to that of 4-HO-MiPT and 4-AcO-MiPT, but the efficacy for doing so is markedly lower: 34 head twitches versus around 77–80 head twitches per 30 minutes for the aforementioned compounds.[4][7]
Chemistry
4-MeO-MiPT is synthetic derivative of the substituted tryptamine and 4-methoxytryptamine families.[1][3] It is the 4-methoxy analogue of N-methyl-N-isopropyltryptamine (MiPT) and the O-methyl ether of 4-HO-MiPT.[1][3]
Synthesis
The chemical synthesis of 4-MeO-MiPT has been described.[1][5]
Analogues
Analogues of 4-MeO-MiPT include N-methyl-N-isopropyltryptamine (MiPT), 4-methoxytryptamine (4-MeO-T), 4-MeO-DiPT, 4-MeO-DMT, 4-HO-MiPT, 4-AcO-MiPT, 5-MeO-MiPT, 5-MeO-DMT, and psilocin (4-HO-DMT), among others.[1][3]
History
4-MeO-MiPT was first described in the scientific literature by David Repke and Alexander Shulgin and colleagues in 1985.[5] Subsequently, it was described in greater detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known Loved) as entry #39.[1] The pharmacology of 4-MeO-MiPT was studied and described in the 2020s.[3][4] It was reported as a novel designer drug by at least 2016.[6][2]
Society and culture
Legal status
Canada
4-MeO-MiPT is not an explicitly nor implicitly controlled substance in Canada as of 2025.[8]
United States
4-MeO-MiPT is not an explicitly controlled substance in the United States.[9] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.