MAM, also known as 2,5-dimethoxy-4-pentyloxyamphetamine or as TMA2-4-PeO, is a chemical compound 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." [...] "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." [...] "As to the preparation of MAM, the exact same sequence was used, except for the employment of n-amyl bromide. The benzaldehyde crystallized from methanol with a mp of 79–80 °C, and formed a malononitrile derivative which was bright yellow and melted at 103–104 °C. The nitrostyrene, when pure, melted at 57–58.5 °C but proved very difficult to separate from the aldehyde. The final product, 4-n-amyloxy-2,5-dimethoxyamphetamine 4-n-amyl-2,5-dimethoxyamphetamine hydrochloride (MAM) was obtained by lithium aluminum hydride reduction in ether and melted at 125–127 °C. It was assayed at up to 16 milligrams, at which level there was noted a heaviness in the chest and head at the 2-hour point, but no cardiovascular disturbance and no mydriasis. This was called an inactive level, and no higher one has yet been tried." 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), MAM produced a brief heaviness in the chest and head at a dose of 16mg orally. However, it caused no other effects, for instance psychoactive effects, cardiovascular disturbances, or pupil dilation, and was deemed inactive up to that dose level. Higher doses were not tested. As such, the properties and effects of MAM remain unknown. The chemical synthesis of MAM has been described. MAM was first described in the literature by Shulgin in PiHKAL in 1991.

See also DOx (psychedelics) MEM § Derivatives DOAM

References

External links MAM - Isomer Design