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3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as sass, is an empathogen-entactogen, stimulant, 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).
MDMA produces 3,4-methylenedioxyamphetamine (MDA) as a minor active metabolite. [116] Peak levels of MDA are about 5 to 10% of those of MDMA and total exposure to MDA is almost 10% of that of MDMA with oral MDMA administration. [116] [180] As a result, MDA may contribute to some extent to the effects of MDMA.
3,4-Dihydroxymethamphetamine (HHMA, 3,4-DHMA), or 3,4-dihydroxy-N-methylamphetamine, also known as α-methylepinine or α,N-dimethyldopamine, is the major metabolite of 3,4-methylenedioxy-N-methylamphetamine (MDMA). [1] [2] [3] It is formed from MDMA by O-demethylation via cytochrome P450 enzymes including CYP2D6 as well as CYP1A2 and CYP3A4.
[2] [3] It has since been used to treat a range of disorders from asthma to ADHD and illicitly for recreational purposes. Amphetamine-type stimulants contain chemical groups including unsubstituted phenyl ring , a methyl group at the alpha-position, and primary amino group, which accounts for its psychostimulant activities.
MMDA (3-methoxy-4,5-methylenedioxyamphetamine; 5-methoxy-MDA) is a psychedelic and entactogen drug of the amphetamine class. It is an analogue of lophophine, MDA, and MDMA. MMDA was described by Alexander Shulgin in his book PiHKAL. Shulgin lists the dosage range of MMDA as 100–250 mg.
3,4-Methylenedioxy-N-ethylamphetamine (MDEA; also called MDE and colloquially, Eve) is an empathogenic psychoactive drug. MDEA is a substituted amphetamine and a substituted methylenedioxyphenethylamine. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor. [1] Possession of MDEA is illegal in most ...
3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH, N-hydroxytenamphetamine) is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. [1] It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of MDHMA. MDOH was first synthesized and assayed by Alexander Shulgin. [2]
These can be broadly divided into (i) compounds where the methylenedioxyphenyl ring is retained but the phenethyl portion is modified, or (ii) compounds which retain the 3,4-cyclised amphetamine core common to the MDxx compounds, but have the 1,3-benzodioxole ring replaced by related heterocycles.