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. 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 4,400 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. 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


