Methallylescaline

Methallylescaline, abbreviated as MAL and also known as 4-methylallyloxy-3,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug.^[1] It is the 4-methyl analog of allylescaline. MAL was first synthesized by Alexander Shulgin. It has been sold as a designer drug.^[3][4]

Methallylescaline

Clinical data
Other names	MAL; 4-Methylallyloxy-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-methylallyloxyphenethylamine
Routes of administration	Oral[1]
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[2]
Pharmacokinetic data
Duration of action	12–16 hours[1]
Identifiers
IUPAC name 2-{3,5-Dimethoxy-4-[(2-methylprop-2-en-1-yl)oxy]phenyl}ethan-1-amine
CAS Number	207740-41-8 Y
PubChem CID	44350127
ChemSpider	21106346 Y
UNII	CVN0S9V910
ChEMBL	ChEMBL126803 Y
CompTox Dashboard (EPA)	DTXSID20658380
Chemical and physical data
Formula	C14H21NO3
Molar mass	251.326 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(=C)COc1c(cc(cc1OC)CCN)OC
InChI InChI=1S/C14H21NO3/c1-10(2)9-18-14-12(16-3)7-11(5-6-15)8-13(14)17-4/h7-8H,1,5-6,9,15H2,2-4H3 Y Key:FOXJFBFFGULACD-UHFFFAOYSA-N Y
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Use and effects

In his book PiHKAL, Shulgin lists the dose range of methallylescaline as 40 to 65 mg and its duration as 12 to 16 hours.^[1] It has been said to have an unusually steep dose–response curve, such that a small increase in dose can result in an unexpectedly large increase in effects.^[5] The effects of MAL are comparable to that of other mescaline analogues, although with a longer duration.^[1]

Pharmacology

Methallylescaline acts as a potent agonist of the serotonin 5-HT_2A receptor.^[6] It also interacts with certain other targets.^[6]

Society and culture

Legal status

Sweden

Methallylescaline is illegal in Sweden as of 26 January 2016.^[7]

United States

Methallylescaline is not directly scheduled under the Controlled Substances Act. However, due to its structural similarities with mescaline, it could potentially be prosecuted under the Federal Analogue Act if sold for human consumption.

See also

• Substituted mescaline analogue
• 2C-T-3
• 2C-T-13
• 3C-MAL