5-Methyl-MDA

5-Methyl-3,4-methylenedioxyamphetamine (5-Methyl-MDA) is an entactogen and psychedelic designer drug of the amphetamine class. It is a ring-methylated homologue of MDA and a structural isomer of MDMA.^[1]

5-Methyl-MDA

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class A US: Analogue to a Schedule I/II drug (possibly, if human consumption intent can be proven)
Identifiers
IUPAC name 1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number	749191-14-8 N 204916-89-2 (HCl)
PubChem CID	10012829
ChemSpider	8188403 Y
UNII	10R3PP3FVM
ChEMBL	ChEMBL6330 Y
CompTox Dashboard (EPA)	DTXSID101024547
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.246 g·mol−1
3D model (JSmol)	Interactive image
SMILES O2COc1c2cc(CC(N)C)cc1C
InChI InChI=1S/C11H15NO2/c1-7-3-9(4-8(2)12)5-10-11(7)14-6-13-10/h3,5,8H,4,6,12H2,1-2H3 Y Key:OLENSVFSNAULML-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Effects and research

Drug discrimination studies showed that 5-methyl-MDA substitutes for MDA, MMAI, and LSD, but not amphetamine, suggesting that it produces a mix of entactogen and hallucinogenic effects without any stimulant effects.^{[citation needed]}

5-Methyl-MDA acts as a selective serotonin releasing agent (SSRA) with IC₅₀ values of 107nM, 11,600nM, and 1,494nM for serotonin, dopamine, and norepinephrine efflux.^[1] It is over 5 times more potent than MDA in vitro assays, with a suitable active dose possibly in vivo being around 15–25 mg.^[1] Subsequent testing in vivo, however, has found that it is not as potent as once thought and is active at at least 100 mg. 2-Methyl-MDA is also much more potent than MDA, but is not quite as potent as 5-methyl-MDA.^[1] 6-methyl-MDMA (also known as Madam-6) is mostly inactive, likely due to steric hindrance.^[1][2]

Recent research has used data on 2-methyl-MDA and 5-methyl-MDA to help guide computer modeling of the serotonin transporter complex.^[3]

Legal status

5-Methyl-MDA is not scheduled by the United Nations' Convention on Psychotropic Substances.^[4]

United States

5-Methyl-MDA is not scheduled at the federal level in the United States,^[5] but it is possible that 5-Methyl-MDA could legally be considered an analog of MDA, in which case, sales or possession could potentially be prosecuted under the Federal Analogue Act.^[6]