Para-Methoxymethamphetamine

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 (ecstasy) 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).