MALM (drug)

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]

MALM

Clinical data
Other names	4-Allyloxy-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-allyloxyamphetamine
Drug class	Serotonin 5-HT2 receptor agonist
ATC code	None
Identifiers
IUPAC name 1-{2,5-dimethoxy-4-[(prop-2-en-1-yl)oxy]phenyl}propan-2-amine
Chemical and physical data
Formula	C14H21NO3
Molar mass	251.326 g·mol−1
3D model (JSmol)	Interactive image
SMILES C=CCOc1cc(OC)c(cc1OC)CC(N)C
InChI 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

Use and effects

The properties and effects of MALM in humans do not appear to be known.^[3]

Pharmacology

MALM acts as a potent agonist of the serotonin 5-HT₂ receptors.^[1][2] Its affinities (K_i) were 150 nM for the serotonin 5-HT_2A receptor and 900 nM for the serotonin 5-HT_2C receptor, whereas its activational potencies (EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy)) were 2.9 nM (89%) at the serotonin 5-HT_2A receptor and 9.5 nM (101%) at the serotonin 5-HT_2B 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]

History

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

• DOx (psychedelics)
• MEM § Derivatives
• Allylescaline
• 3C-AL