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MMALM
Clinical data
Other names4-Methallyloxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-methallyloxyamphetamine
Drug classSerotonin 5-HT2 receptor agonist
ATC code
  • None
Identifiers
  • 1-{2,5-dimethoxy-4-[(2-methylprop-2-en-1-yl)oxy]phenyl}propan-2-amine
Chemical and physical data
FormulaC15H23NO3
Molar mass265.353 g·mol−1
3D model (JSmol)
  • COc1cc(CC(N)C)c(cc1OCC(=C)C)OC
  • InChI=1S/C15H23NO3/c1-10(2)9-19-15-8-13(17-4)12(6-11(3)16)7-14(15)18-5/h7-8,11H,1,6,9,16H2,2-5H3
  • Key:FKOOHEYOIKURNB-UHFFFAOYSA-N

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]

Pharmacology

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

History

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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

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References

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  1. ^ a b c d e 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. ^ a b c d 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. ^ a b c d e f g h i 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.
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