6-Methyl-MDA

6-Methyl-MDA
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar laws in other countries);
Identifiers
	IUPAC name 1-(6-Methyl-1,3-benzodioxol-5-yl)propan-2-amine;
CAS Number	246861-21-2;
PubChem CID	10511982;
ChemSpider	8687383 ;
ChEMBL	ChEMBL6376 ;
CompTox Dashboard (EPA)	DTXSID501029470 ;
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.246 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O1c2cc(c(cc2OC1)CC(N)C)C;
	InChI InChI=1S/C11H15NO2/c1-7-3-10-11(14-6-13-10)5-9(7)4-8(2)12/h3,5,8H,4,6,12H2,1-2H3 ; Key:HCFHWXDIZOAUTQ-UHFFFAOYSA-N ;
	(verify)

6-Methyl-3,4-methylenedioxyamphetamine (6-Methyl-MDA) is an entactogen and psychedelic drug of the amphetamine class.^[1] It was first synthesized in the late 1990s by a team including David E. Nichols at Purdue University while investigating derivatives of 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxy-N-methylamphetamine (MDMA).^[1]

6-Methyl-MDA has IC₅₀ values of 783 nM, 28,300 nM, and 4,602 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine in rat synaptosomes.^[1] In animal studies it substitutes for MBDB, MMAI, LSD, and 2,5-dimethoxy-4-iodoamphetamine (DOI), though not amphetamine, but only partially and at high doses.^[1] Thus, while several-fold less potent than its analogues 2-methyl-MDA and 5-methyl-MDA, and approximately half as potent as MDA, 6-methyl-MDA is still significantly active,^[1] and appropriate doses may be similar to or somewhat higher than those of MDMA.^{[citation needed]}

References

^ ^a ^b ^c ^d ^e Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE (March 1998). "Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry. 41 (6): 1001–5. CiteSeerX 10.1.1.688.9559. doi:10.1021/jm9705925. PMID 9526575.