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

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 (EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy)) 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

Canada

MMALM is a controlled substance in Canada under phenethylamine blanket-ban language.[4]

See also

References

  1. 1 2 3 4 5 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. pp. 786–787. ISBN 978-3-03788-700-4. OCLC 858805226.
  2. 1 2 3 4 Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. 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. 1 2 3 4 5 6 7 8 9 Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019). "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines". Frontiers in Pharmacology. 10 1423. doi:10.3389/fphar.2019.01423. PMC 6893898. PMID 31849671.
  4. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
source: https://en.wikipedia.org/wiki/4-Methallyloxy-2,5-dimethoxyamphetamine