MMALM
Pharmaceutical compound
From Wikipedia, the free encyclopedia
MMALM, also known as 4-methallyloxy-2,5-dimethoxyamphetamine, is a serotonin receptor modulator 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][3] The drug is also the α-methyl or amphetamine analogue of 2C-O-3.[1][3]
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| Clinical data | |
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| Other names | 4-Methallyloxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-methallyloxyamphetamine |
| Drug class | Serotonin 5-HT2 receptor agonist |
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| Identifiers | |
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| Chemical and physical data | |
| Formula | C15H23NO3 |
| Molar mass | 265.353 g·mol−1 |
| 3D model (JSmol) | |
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Use and effects
The properties and effects of MMALM in humans do not appear to be known.[1]
Pharmacology
Pharmacodynamics
MMALM acts as a potent agonist of the serotonin 5-HT2 receptors.[2][3] Its affinities (Ki) were 61 nM for the serotonin 5-HT2A receptor and 290 nM for the serotonin 5-HT2C receptor, whereas its activational potencies (EC50 (Emax)) were 1.5 nM (95%) at the serotonin 5-HT2A receptor and 29 nM (90%) at the serotonin 5-HT2B receptor.[2][3] Besides the serotonin 5-HT2 receptors, the drug showed little to no activity at various other assessed targets, such as the monoamine transporters.[3] It does not appear to have been tested for psychedelic-like activity in animals.[3]
History
MMALM was first described in the scientific literature by Daniel Trachsel in 2013.[1] Subsequently, it was characterized in more detail by a group including Trachsel and Matthias Liechti in 2019.[2][3] The compound's name is said to derive from its benzene ring substituents, "methoxy methallyloxy methoxy".[3]
Society and culture
Legal status
Canada
MMALM is a controlled substance in Canada under phenethylamine blanket-ban language.[4]