Chemistry:MMALM

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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]

Use and effects

The properties and effects of MMALM in humans do not appear to be known.[1]

Pharmacology

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]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 786–787. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  2. ↑ 2.0 2.1 2.2 2.3 "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews 124 (1): 124–163. January 2024. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. "When an α-methyl group was introduced to the aminoalkyl chain of compounds 2C-O-3 (63) and 2C-O-16 (76), leading to compounds MMALM (86) and MALM (87), the binding affinity and functional activity were not significantly influenced (86, Ki = 61 nM ([3 H]-ketanserin), EC50= 1.5 nM (95%); 87, Ki = 150 nM, EC50= 2.9 nM (89%)) (Figure 11B).171". 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8 "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines". Frontiers in Pharmacology 10. 2019. doi:10.3389/fphar.2019.01423. PMID 31849671. 




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