Chemistry:4-MeO-MiPT
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]
It acts as a serotonin reuptake inhibitor and as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[2][3] The drug produces psychedelic-like effects in animals.[3]
4-MeO-MiPT was first described by David Repke and Alexander Shulgin and colleagues in 1985.[4] 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.[5][6] Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-MeO-MiPT.[1][2]
Use and effects
Shulgin found the effective dose 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][4][6] 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][6] Online anecdotal reports describe 4-MeO-MiPT as producing mild psychedelic effects with little body load.[6]
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 347–731 (Ki) 1,490 (EC50) 99% (Emax) |
| 5-HT2A | 178 (Ki) 376a (EC50) 63% (Emax) |
| 5-HT2C | 510 (Ki) 120a (EC50) 82%a (Emax) |
| SERT | 38 (Ki) 53–57 (IC50) |
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-HT2C receptors.[2][3] Affinities towards receptors outside of the serotonin receptor family have not yet been assessed.[2][3]
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][2] This profile makes 4-MeO-MiPT a potential candidate for elucidating the role of SERT blockade in the mechanisms underlying serotonergic psychedelic action.[2][3]
The drug induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[3] 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 80 head twitches per 30 minutes for the aforementioned compounds.[3]
Chemistry
4-MeO-MiPT is synthetic derivative of the substituted tryptamine and 4-methoxytryptamine families.[1][2] It is the 4-methoxy analogue of N-methyl-N-isopropyltryptamine (MiPT) and the O-methyl ether of 4-HO-MiPT.[1][2]
Synthesis
The chemical synthesis of 4-MeO-MiPT has been described.[1][4]
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][2]
History
4-MeO-MiPT was first described in the scientific literature by David Repke and Alexander Shulgin and colleagues in 1985.[4] 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.[2][3] It was reported as a novel designer drug by at least 2016.[5][6]
Society and culture
Legal status
Canada
4-MeO-MiPT is not an explicitly nor implicitly controlled substance in Canada as of 2025.[7]
United States
4-MeO-MiPT is not an explicitly controlled substance in the United States.[8] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.
See also
References
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. http://www.erowid.org/library/books_online/tihkal/tihkal39.shtml
- ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 Cite error: Invalid
<ref>tag; no text was provided for refs namedKozell_2023 - ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 Cite error: Invalid
<ref>tag; no text was provided for refs namedGlatfelter_2024 - ↑ 4.0 4.1 4.2 4.3 "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". Journal of Medicinal Chemistry 28 (7): 892–896. July 1985. doi:10.1021/jm00145a007. PMID 4009612.
- ↑ 5.0 5.1 "Test purchase of new synthetic tryptamines via the Internet: Identity check by GC-MS and separation by HPLC". Journal of Applied Pharmaceutical Science: 028–034. 2016. doi:10.7324/JAPS.2016.600105. ISSN 2231-3354. https://www.japsonline.com/admin/php/uploads/1744_pdf.pdf. Retrieved 24 October 2025.
- ↑ 6.0 6.1 6.2 6.3 6.4 "4-MeO-MIPT (4-MeOMiPT)" (in ru). https://aipsin.com/newsubstance/334/.
- ↑ "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html.
- ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf
External links
- 4-MeO-MiPT - Isomer Design
- 4-MeO-MiPT - TiHKAL - Erowid
- 4-MeO-MiPT - TiHKAL - Isomer Design
- The Big & Dandy 4-MeO-MiPT Thread - Bluelight
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