2,5-Dimethoxy-4-ethoxyamphetamine

MEM
Clinical data
Other names	2,5-Dimethoxy-4-ethoxyamphetamine; 4-Ethoxy-2,5-dimethoxyamphetamine; MEM; TMA2-4-EtO
Routes of; administration	Oral
Drug class	Serotonin receptor agonist; Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	CA: Schedule I; UK: Class B;
Pharmacokinetic data
Duration of action	10–14 hours
Identifiers
	IUPAC name 1-[(4-ethoxy-2,5-dimethoxy)phenyl]propan-2-amine;
CAS Number	16128-88-4 ;
PubChem CID	542053;
ChemSpider	472023 ;
UNII	3I0ORO8174;
ChEMBL	ChEMBL8225 ;
CompTox Dashboard (EPA)	DTXSID00337348 ;
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c1cc(OC)c(cc1OC)CC(N)C)CC;
	InChI InChI=1S/C13H21NO3/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 ; Key:ITZLAXJQDMGDEO-UHFFFAOYSA-N ;
	(verify)

MEM, also known as 2,5-dimethoxy-4-ethoxyamphetamine or as TMA2-4-EtO, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 4 position has been replaced with an ethoxy group. The drug was first described in the scientific literature by Alexander Shulgin by 1968.