Substituted ethylenedioxyphenethylamine

The substituted ethylenedioxyphenethylamines (EDxx) are a small group of psychoactive drugs of the phenethylamine family related to the substituted methylenedioxyphenethylamines (MDxx).^[1][2][3] They include the amphetamines 3,4-ethylenedioxyamphetamine (EDA), 3,4-ethylenedioxy-N-methylamphetamine (EDMA; "MDMC"), and 3-methoxy-4,5-ethylenedioxyamphetamine (MEDA; 5-methoxy-EDA) and the cathinone 3,4-ethylenedioxymethcathinone (EDMC), among others.^[1][2][3]

EDxx compounds have been found act as monoamine releasing agents, including of serotonin, norepinephrine, and/or dopamine.^{[4][5][6][7][8]} However, they showed reduced potency in these assays compared to their MDxx counterparts like MDMA, MMDA (5-methoxy-MDA), and methylone (MDMC).^{[4][5][6][7][8]} Some, such as EDMA, have been assessed and variably found to produce psychoactive effects in humans.^[1][2] These effects have included paresthesia, nystagmus, sedation, hypnagogic imagery, and/or mild visual effects.^[1] However, at assessed doses, there were no entactogenic or stimulant effects and no or only mild hallucinogenic effects at best, which led to conclusions that they were essentially inactive.^[1][2][3]

EDxx compounds were tested by Alexander Shulgin and described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1][2][3] They were first described in the scientific literature by Shulgin by 1964.^[9][10][11]