para-Methoxyamphetamine

PMA
Clinical data
Other names	para-Methoxyamphetamine; p-Methoxyamphetamine; PMA; 4-Methoxyamphetamine; 4-MA; 4-MeO-A; 4-OMe-PIA
Routes of; administration	Oral
Drug class	Serotonin releasing agent; Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen; Monoamine oxidase inhibitor
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I; In general illegal unless for medical, therapeutic or scientific use.;
Pharmacokinetic data
Duration of action	"Short"
Identifiers
	IUPAC name 1-(4-methoxyphenyl)propan-2-amine;
CAS Number	64-13-1 ;
PubChem CID	31721;
DrugBank	DB01472 ;
ChemSpider	29417 ;
UNII	OVB8F8P39Q;
KEGG	C22811 ;
ChEMBL	ChEMBL278663 ;
CompTox Dashboard (EPA)	DTXSID7040578 ;
ECHA InfoCard	100.000.525
Chemical and physical data
Formula	C10H15NO
Molar mass	165.236 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC(=CC=C1CC(C)N)OC;
	InChI InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3 ; Key:NEGYEDYHPHMHGK-UHFFFAOYSA-N ;
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para-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogenic effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.

PMA has been found in tablets touted as MDMA (ecstasy) although its effects are markedly different compared to those of MDMA. The consequences of such deception have often included hospitalization and death for unwitting users. PMA is commonly synthesized from anethole, the flavor compound of anise and fennel, mainly because the starting material for MDMA, safrole, has become less available due to law enforcement action, causing illicit drug manufacturers to use anethole as an alternative.