Para-Methoxy-N-methylamphetamine

para-Methoxy-N-methylamphetamine

Legal status
Legal status	CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Analogue to a Schedule I/II drug
Identifiers
IUPAC name 1-(4-Methoxyphenyl)-N-methylpropan-2-amine
CAS Number	22331-70-0 Y
PubChem CID	90766
ChemSpider	81951
UNII	037U5SR9KL
ECHA InfoCard	100.020.242
Chemical and physical data
Formula	C11H17NO
Molar mass	179.259 g/mol
3D model (Jmol)	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

para-Methoxy-N-methylamphetamine (also known as PMMA, Red Mitsubishi), chemically known as methyl-MA, 4-methoxy-N-methylamphetamine, 4-MMA) or (4-PMDA, as listed to its original physical name.) is a stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). PMMA is the 4-methoxy analog 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.

Its effects in humans are reputedly similar to those of PMA, but slightly more empathogenic in nature. It has a reduced tendency to produce severe hyperthermia at low dosages, but at higher dosages side effects and risk of death becomes 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). Shulgin reported that PMMA produces an increase in blood pressure and in heart rate, at doses above 100 mg, but causes no psychoactive effects at these levels.