MIPM

MIPM
Clinical data
Other names4-Isopropoxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-isopropoxyamphetamine
Routes of
administration		Unknown[1][2]
Drug classSerotonin 5-HT2 receptor agonist
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1][2]
Identifiers
  • 1-(2,5-dimethoxy-4-propan-2-yloxyphenyl)propan-2-amine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC14H23NO3
Molar mass253.342 g·mol−1
3D model (JSmol)
  • CC(C)OC1=C(C=C(C(=C1)OC)CC(C)N)OC
  • InChI=1S/C14H23NO3/c1-9(2)18-14-8-12(16-4)11(6-10(3)15)7-13(14)17-5/h7-10H,6,15H2,1-5H3
  • Key:UEUXKMHRZTVVCQ-UHFFFAOYSA-N

MIPM, also known as 4-isopropoxy-2,5-dimethoxyamphetamine, is a serotonin receptor modulator and possible psychedelic drug of the phenethylamine, amphetamine, and DOx families.[1][2][3] It is a derivative of the DOx psychedelics TMA-2 and MEM in which the 4-position substituent has been extended.[1][3] The drug is also the α-methyl or amphetamine analogue of 2C-O-4.[1][3]

Use and effects

The properties and effects of MIPM in humans do not appear to be known.[1][2]

Pharmacology

Pharmacodynamics

MIPM acts as a low-potency agonist of the serotonin 5-HT2 receptors.[3] Its affinities (Ki) were 4,400 nM for the serotonin 5-HT2A receptor and 9,030 nM for the serotonin 5-HT2C receptor, whereas its activational potencies (EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy)) were 990 nM (47%) at the serotonin 5-HT2A receptor and 180 nM (20%) at the serotonin 5-HT2B receptor.[3] Besides the serotonin 5-HT2 receptors, the drug showed little to no activity at various other assessed targets, such as the monoamine transporters.[3] It does not appear to have been tested for psychedelic-like activity in animals.[3]

Chemistry

Synthesis

The chemical synthesis of MIPM has been described.[1]

Analogues

Analogues of MIPM include TMA-2, MEM, and MPM, among others.[1][2]

History

MIPM was first described in the literature by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved).[1] He synthesized the compound, but discouraged by the reduced activity of MPM compared to TMA-2 and MEM, did not test it in humans.[1] Subsequently, MIPM was characterized in more detail by a group including Daniel Trachsel and Matthias Liechti in 2019.[3] The compound's name is said to derive from its benzene ring substituents, "methoxy isopropoxy methoxy".[3]

Society and culture

Canada

MIPM is a controlled substance in Canada under phenethylamine blanket-ban language.[4]

See also

References

  1. ^ a b c d e f g h i j Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "The extension of the 4-alkoxy-group led to the discovery of the TMA-2—MEM—MIPM—MPM—MBM series of amphetamine analogues. The 2-carbon counterparts of these would be a fascinating series to explore, I thought, if there was some encouragement to be had from a preliminary try in this field. This was a first shot in the dark, the actual trial example, and it certainly didn’t provide much encouragement. The three-carbon analogue, MIPM, was made (q.v.) but not explored, following the disappointing trials of MPM. If this area is ever re-opened, the numbering should reasonably follow the sulfur materials. The 4-ethoxy material would be 2C-O-2, the 4-n-propoxy compound 2C-O-7, and the 4-n-butoxy compound 2C-O-19. These are the exact analogues of 2C-T-2, 2C-T-7, and 2C-T-19, resp., and the 2-carbon homologues of MEM, MPM, and MBM. [...] The 4-propoxy homologue of TMA-2 and MEM is clearly less active, and this has discouraged me from putting too much more effort in this direction. Three additional materials of this pattern were prepared and either shown to be even less active, or simply were not assayed at all. These are the 4-isopropoxy isomer (MIPM), the n-butoxy homologue (MBM), and the n-amyl homologue (MAM). They scarcely warrant separate recipes as they were all made in a manner similar to this one describing MPM. For the preparation of MIPM, [...] The molecular structure had a pleasant appeal to it, with a complete reflection symmetry shown by the atoms of the amphetamine side chain and the isopropoxy side chain. But the nature of the actual product in hand had no appeal at all, and no assay was ever started."
  2. ^ a b c d e Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  3. ^ a b c d e f g h i Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019). "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines". Frontiers in Pharmacology. 10 1423. doi:10.3389/fphar.2019.01423. PMC 6893898. PMID 31849671.
  4. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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