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 ñ-methyl or amphetamine analogue of 2C-O-4.
The properties and effects of MIPM in humans do not appear to be known.
MIPM acts as a low-potency agonist of the serotonin 5-HT<sub>2</sub> receptors. Its affinities (K<sub>i</sub>) were 4,400nM for the serotonin 5-HT<sub>2A</sub> receptor and 9,030nM for the serotonin 5-HT<sub>2C</sub> receptor, whereas its activational potencies ( ()) were 990nM (47%) at the serotonin 5-HT<sub>2A</sub> receptor and 180nM (20%) at the serotonin 5-HT<sub>2B</sub> receptor. Besides the serotonin 5-HT<sub>2</sub> 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.
The chemical synthesis of MIPM has been described.
Analogues of MIPM include TMA-2, MEM, and MPM, among others.
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".
MIPM is a controlled substance in Canada under phenethylamine blanket-ban language.