2,3-Methylenedioxymethamphetamine

ORTHO-MDMA, also known as 2,3-methylenedioxymethamphetamine (2,3-MDMA), is a positional isomer of the recreational drug 3,4-MDMA (commonly known as Ecstasy or Molly).^[1] It is a monoamine transporter (MAT) substrate and inhibitor similarly to 3,4-MDMA.^[2] However, while showing similar potency at the norepinephrine transporter (NET), 2,3-MDMA is less potent at the serotonin transporter (SERT).^[2] 2,3-MDMA has not been encountered as a recreational or designer drug.^[2]

2,3-Methylenedioxymethamphetamine

Clinical data
Other names	2,3-MDMA; 2,3-Methylenedioxy-N-methylamphetamine; ORTHO-MDMA
ATC code	None
Identifiers
IUPAC name 1-(1,3-Benzodioxol-4-yl)-N-methylpropan-2-amine
CAS Number	168967-99-5
PubChem CID	95162631
ChemSpider	23255735
UNII	QNH0322FHX
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.246 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=C2C(=CC=C1)OCO2)NC
InChI InChI=1S/C11H15NO2/c1-8(12-2)6-9-4-3-5-10-11(9)14-7-13-10/h3-5,8,12H,6-7H2,1-2H3/t8-/m0/s1 Y Key:RTZIIFGBTSUSEL-QMMMGPOBSA-N Y

See also

• 2,3-Methylenedioxyamphetamine (2,3-MDA)
• 1-Naphthylmethcathinone (AMAPN)