3,4-Methylenedioxyamphetamine

3,4-Methylenedioxyamphetamine (also known as MDA and sass) is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal. MDA is rarely sought as a recreational drug compared to other amphetamines; however, it remains an important and widely used drug due to it being a primary metabolite, the product of hepatic N-dealkylation, of MDMA (ecstasy). It is also a common adulterant of illicitly produced MDMA. MDA currently has no accepted medical use. MDA is bought, sold, and used as a recreational 'love drug', due to its enhancement of mood and empathy. A recreational dose of MDA is sometimes cited as being between 100 and 160 mg. MDA produces serotonergic neurotoxic effects, thought to be activated by initial metabolism of MDA. In addition, MDA activates a response of the neuroglia, though this subsides after use. Symptoms of acute toxicity may include agitation, sweating, increased blood pressure and heart rate, dramatic increase in body temperature, convulsions, and death. Death is usually caused by cardiac effects and subsequent hemorrhaging in the brain (stroke). MDA is a substrate of the serotonin, norepinephrine, dopamine, and vesicular monoamine transporters, as well as a TAAR1 agonist, and for these reasons acts as a reuptake inhibitor and releasing agent of serotonin, norepinephrine, and dopamine (that is, it is an ()). It is also an agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors and shows affinity for the α2A-, α2B-, and α2C-adrenergic receptors and serotonin 5-HT1A and 5-HT7 receptors. The (S)-optical isomer of MDA is more potent than the (R)-optical isomer as a psychostimulant, possessing greater affinity for the three monoamine transporters.