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. "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." It is a derivative of the DOx psychedelics TMA-2 and MEM in which the 4-position substituent has been extended. The drug is also the α-methyl or amphetamine analogue of 2C-O-4.
Use and effects The properties and effects of MIPM in humans do not appear to be known.
Pharmacology Pharmacodynamics MIPM acts as a low-potency agonist of the serotonin 5-HT2 receptors. Its affinities (Ki) were 4,400nM for the serotonin 5-HT2A receptor and 9,030nM for the serotonin 5-HT2C receptor, whereas its activational potencies ( ()) were 990nM (47%) at the serotonin 5-HT2A receptor and 180nM (20%) at the serotonin 5-HT2B receptor. Besides the serotonin 5-HT2 receptors, the drug showed little to no activity at various other assessed targets, such as the monoamine transporters. It does not appear to have been tested for psychedelic-like activity in animals.
Chemistry Synthesis The chemical synthesis of MIPM has been described.
Analogues Analogues of MIPM include TMA-2, MEM, and MPM, among others.
History MIPM was first described in the literature by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved). He synthesized the compound, but discouraged by the reduced activity of MPM compared to TMA-2 and MEM, did not test it in humans. Subsequently, MIPM was characterized in more detail by a group including Daniel Trachsel and Matthias Liechti in 2019. The compound's name is said to derive from its benzene ring substituents, "methoxy isopropoxy methoxy".
Society and culture Legal status Canada MIPM is a controlled substance in Canada under phenethylamine blanket-ban language.
See also DOx (psychedelics) MEM § Derivatives Isoproscaline 2C-T-4
References
External links MIPM - Isomer Design