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.[1][2][3] It is a derivative of the DOx psychedelics TMA-2 and MEM in which the 4-position substituent has been extended.[1][2][3] 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 16 mg orally.[1][2][3] However, it caused no other effects, for instance psychoactive effects, cardiovascular disturbances, or pupil dilation, and was deemed inactive up to that dose level.[1][2][3] Higher doses were not tested.[1][2][3] As such, the properties and effects of MAM remain unknown.[1][2][3] The chemical synthesis of MAM has been described.[1] MAM was first described in the literature by Shulgin in PiHKAL in 1991.[1][2]
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| Other names | 4-Pentyloxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-pentyloxyamphetamine; 4-Amyloxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-amyloxyamphetamine; TMA2-4-PeO |
| Routes of administration | Oral[1][2][3] |
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| Duration of action | Unknown[1][2][3] |
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| Formula | C16H27NO3 |
| Molar mass | 281.396 g·mol−1 |
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See also
editReferences
edit- 1 2 3 4 5 6 7 8 9 10 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "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."
- 1 2 3 4 5 6 7 8 9 Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
- 1 2 3 4 5 6 7 8 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.