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MALM (drug)

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MALM
Clinical data
Other names4-Allyloxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-allyloxyamphetamine
Drug classSerotonin 5-HT2 receptor agonist
ATC code
  • None
Identifiers
  • 1-{2,5-dimethoxy-4-[(prop-2-en-1-yl)oxy]phenyl}propan-2-amine
Chemical and physical data
FormulaC14H21NO3
Molar mass251.326 g·mol−1
3D model (JSmol)
  • C=CCOc1cc(OC)c(cc1OC)CC(N)C
  • InChI=1S/C14H21NO3/c1-5-6-18-14-9-12(16-3)11(7-10(2)15)8-13(14)17-4/h5,8-10H,1,6-7,15H2,2-4H3
  • Key:VBAQDLWNBQBWPR-UHFFFAOYSA-N

MALM, also known as 4-allyloxy-2,5-dimethoxyamphetamine, is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.[1][2] It is a derivative of the DOx psychedelics TMA-2 and MEM in which the 4-position substituent has been extended.[2] The drug is also the α-methyl or amphetamine analogue of 2C-O-16.[2]

Pharmacology

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MALM acts as a potent agonist of the serotonin 5-HT2 receptors.[1][2] Its affinities (Ki) were 150 nM for the serotonin 5-HT2A receptor and 900 nM for the serotonin 5-HT2C receptor, whereas its activational potencies (EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy)) were 2.9 nM (89%) at the serotonin 5-HT2A receptor and 9.5 nM (101%) at the serotonin 5-HT2B receptor.[1][2] Besides the serotonin 5-HT2 receptors, the drug showed little to no activity at various other assessed targets, such as the monoamine transporters.[2] It does not appear to have been tested for psychedelic-like activity in animals.[2] Similarly, the properties and effects of MALM in humans do not appear to be known.[3]

History

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MALM was first described in the scientific literature by Daniel Trachsel in 2013.[3] Subsequently, it was characterized in more detail by a group including Trachsel and Matthias Liechti in 2019.[1][2] The compound's name is said to derive from its benzene ring substituents, "methoxy allyloxy methoxy".[2]

See also

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References

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  1. ^ 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
  2. ^ 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.
  3. ^ a b 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.
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