para-Methoxymethamphetamine

PMMA
Clinical data
Other names	PMMA; p-Methoxymethamphetamine; para-Methoxy-N-methylamphetamine; 4-Methoxy-N-methylamphetamine; 4-MMA; Methyl-MA; 4-PMDA
Routes of; administration	Oral
Drug class	Serotonin–norepinephrine releasing agent; Monoamine oxidase inhibitor
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule 1;
Pharmacokinetic data
Onset of action	≤1 hour
Duration of action	"Short"
Identifiers
	IUPAC name 1-(4-Methoxyphenyl)-N-methylpropan-2-amine;
CAS Number	22331-70-0 ;
PubChem CID	90766;
ChemSpider	81951;
UNII	037U5SR9KL;
KEGG	C22810 ;
CompTox Dashboard (EPA)	DTXSID30874251 ;
ECHA InfoCard	100.040.818
Chemical and physical data
Formula	C11H17NO
Molar mass	179.263 g·mol−1
3D model (JSmol)	Interactive image; Interactive image;
	SMILES CC(CC1=CC=C(C=C1)OC)NC; ; C1=CC(=CC=C1CC(C)NC)OC;
	InChI InChI=1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3; Key:UGFMBZYKVQSQFX-UHFFFAOYSA-N;
	(verify)

para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy analogue of methamphetamine.

Little is known about the pharmacological properties, metabolism, and toxicity of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.

PMMA is a serotonin–norepinephrine releasing agent (SNRA) as well as potent monoamine oxidase inhibitor (MAOI). It has a reduced tendency to produce severe hyperthermia at low doses compared to PMA, but at higher doses, side effects and risk of death become similar to those of PMA.

The synthesis and effects of PMMA were described by American experimental chemist Alexander Shulgin in his book PiHKAL, where it is referred to by the name "methyl-MA", as the N-methylated form of 4-MA (PMA).