MBM, also known as 2,5-dimethoxy-4-butoxyamphetamine or as TMA2-4-BuO, is a serotonin receptor modulator 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." [...] "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." [...] "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 MBM, the starting phenol was alkylated to 2-n-butoxy-1,4-dimethoxybenzene in methanolic KOH with n-butyl bromide. The benzaldehyde melted at 79.5–81 °C from methanol, and formed a malononitrile derivative that had a melting point of 134.5–135 °C. The nitrostyrene from the aldehyde and nitroethane in acetic acid crystallized from methanol with a mp of 71–72 °C. Lithium aluminum hydride reduction in ether gave the ether-insoluble chloroform-soluble product 4-n-butoxy-2,5-dimethoxyamphetamine hydrochloride (MBM) with a melting point of 128–130 °C. This product met all tests for structural integrity, and assays were started. At levels of up to 12.0 milligrams, there were no effects noted." It is a derivative of the DOx psychedelics TMA-2 and MEM in which the 4-position substituent has been extended. According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), MBM produced no effects at doses of up to 12mg orally. Higher doses were not tested. As such, the properties and effects of MBM remain unknown. The drug is a potent full agonist of the serotonin 5-HT2A and 5-HT2C receptors ( () = 26.9nM (114%) and 57.4nM (93%), respectively). Conversely, it is inactive as an agonist of the serotonin 5-HT2B and 5-HT1A receptors. The chemical synthesis of MBM has been described. MBM was first described in the literature by Shulgin in PiHKAL in 1991.

See also DOx (psychedelics) MEM § Derivatives Buscaline

References

External links MBM - Isomer Design