4-MeO-MiPT

Last updated

4-MeO-MiPT
4-MeO-MiPT.svg
4-MeO-MiPT 3D.png
Clinical data
Other names4-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
ATC code
  • None
Pharmacokinetic data
Onset of action 20–40 minutes [1]
Duration of action 4–6 hours [1]
Identifiers
  • N-[2-(4-methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H22N2O
Molar mass 246.354 g·mol−1
3D model (JSmol)
Melting point 80 to 81 °C (176 to 178 °F)
  • CC(N(CCC1=CNC2=C1C(OC)=CC=C2)C)C
  • InChI=InChI=1S/C15H22N2O/c1-11(2)17(3)9-8-12-10-16-13-6-5-7-14(18-4)15(12)13/h5-7,10-11,16H,8-9H2,1-4H3
  • Key:BJIWLHLNPTWSGD-UHFFFAOYSA-N Yes check.svgY
   (verify)

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]

Contents

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] 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] 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]

Interactions

Pharmacology

Pharmacodynamics

4-MeO-MiPT activities
TargetAffinity (Ki, nM)
5-HT1A 347–731 (Ki)
1,490 (EC50 Tooltip half-maximal effective concentration)
99% (Emax Tooltip maximal efficacy)
5-HT2A 178 (Ki)
376a (EC50)
63% (Emax)
5-HT2C 510 (Ki)
120a (EC50)
82%a (Emax)
SERT 38 (Ki)
53–57 ( 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: [2] [3]

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]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. http://www.erowid.org/library/books_online/tihkal/tihkal39.shtml
  2. 1 2 3 4 5 6 7 8 9 10 11 Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". The Journal of Pharmacology and Experimental Therapeutics. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC   10029822 . PMID   36669875.
  3. 1 2 3 4 5 6 7 8 9 Glatfelter G, Walther D, Partilla J, Chadeayne AR, Manke DR, Baumann MH (2024-06-01). "Pharmacological profiles and psychedelic-like effects of 4-hydroxy-, 4-acetoxy-, and 4-methoxy-N- methyl- N- isopropyltryptamine" . The Journal of Pharmacology and Experimental Therapeutics. 389: 281. doi:10.1124/jpet.281.923160. ISSN   0022-3565.
  4. 1 2 3 4 Repke DB, Grotjahn DB, Shulgin AT (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". Journal of Medicinal Chemistry. 28 (7): 892–896. doi:10.1021/jm00145a007. PMID   4009612.
  5. 1 2 Taschwer M, Ebner E, Schmid M (2016). "Test purchase of new synthetic tryptamines via the Internet: Identity check by GC-MS and separation by HPLC" (PDF). Journal of Applied Pharmaceutical Science: 028–034. doi: 10.7324/JAPS.2016.600105 . ISSN   2231-3354 . Retrieved 24 October 2025.
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