The substituted methylenedioxyphenethylamines (abbreviated as MDxx) represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational drugs.

The base compound of the MDxx class is 3,4-methylenedioxyphenethylamine (MDPEA), and the prototypical agent of this class is 3,4-methylenedioxy-N-methylamphetamine (MDMA; "ecstasy"). Other notable MDxx class substances include 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxy-N-ethylamphetamine (MDEA; "Eve"), N-methyl-1,3-benzodioxolylbutanamine (MBDB; "Eden"), and 3,4-methylenedioxy-N-methylcathinone (βk-MDMA; "Methylone"). There are also cyclized phenethylamine MDxx compounds, such as MDAI, MDAT, MDPV, MDPM, and MDMAR.

Use and effects

+ Compound Chemical name Dose Duration MDPEA 3,4-Methylenedioxyphenethylamine >300 mg Unknown Lophophine (MMDPEA; 2C-MMDA) 3-Methoxy-4,5-methylenedioxyphenethylamine ≥150–250 mg Unknown 2C-MMDA-2 (2C-2; MMDPEA-2) 2-Methoxy-4,5-methylenedioxyphenethylamine >2.6 mg Unknown 2C-MMDA-3a (2C-3a; MMDPEA-3a) 2-Methoxy-3,4-methylenedioxyphenethylamine ≥40–120 mg Unknown 2C-MMDA-3b (2C-3b; MMDPEA-3b) 4-Methoxy-2,3-methylenedioxyphenethylamine Unknown Unknown 2C-MMDA-4 (MMDPEA-4) 5-Methoxy-2,3-methylenedioxyphenethylamine Unknown Unknown MDMPEA 3,4-Methylenedioxy-N-methylphenethylamine >30 mg Unknown MDPEA-NBOMe N-(2-Methoxybenzyl)-3,4-methylenedioxyphenethylamine Unknown Unknown Lophophine-NBOMe N-(2-Methoxybenzyl)-3-methoxy-4,5-methylenedioxyphenethylamine Unknown Unknown 2C2-NBOMe N-(2-Methoxybenzyl)-2-methoxy-4,5-methylenedioxyphenethylamine Unknown Unknown BOHH (β-hydroxy-MDPEA) 3,4-Methylenedioxy-β-hydroxyphenethylamine >100 mg Unknown BOH (β-methoxy-MDPEA) 3,4-Methylenedioxy-β-methoxyphenethylamine 80–120 mg 6–8 hours MDA 3,4-Methylenedioxyamphetamine 80–160 mg (20–200 mg+) 4–8 hours (S)-MDA (S)-3,4-Methylenedioxyamphetamine 160–225 mg 3 hours (R)-MDA (R)-3,4-Methylenedioxyamphetamine 70–200 mg 4–8 hours ORTHO-MDA (2,3-MDA) 2,3-Methylenedioxyamphetamine 50 mg "All night" ORTHO-MDMA (2,3-MDMA) 2,3-Methylenedioxy-N-methylamphetamine Unknown Unknown 2-Methyl-MDA 2-Methyl-3,4-methylenedioxyamphetamine ≥40–100 mg 12–20 hours 5-Methyl-MDA 5-Methyl-3,4-methylenedioxyamphetamine Unknown Unknown 6-Methyl-MDA 6-Methyl-3,4-methylenedioxyamphetamine 160 mg 8 hours MMDA (5-methoxy-MDA) 3-Methoxy-4,5-methylenedioxyamphetamine 100–250 mg "Moderate" MMDA-2 (6-methoxy-MDA) 2-Methoxy-4,5-methylenedioxyamphetamine 25–50 mg 8–12 hours MMDA-3a (2-methoxy-MDA) 2-Methoxy-3,4-methylenedioxyamphetamine 20–80 mg 10–16 hours MMDA-3b 4-Methoxy-2,3-methylenedioxyamphetamine ≥60–80 mg Unknown MMDA-4 5-Methoxy-2,3-methylenedioxyamphetamine Unknown Unknown MMDA-5 6-Methoxy-2,3-methylenedioxyamphetamine ≥30 mg Unknown DMMDA (2,5-dimethoxy-MDA) 2,5-Dimethoxy-3,4-methylenedioxyamphetamine 30–75 mg 6–8 hours DMMDA-2 (5,6-dimethoxy-MDA) 2,3-Dimethoxy-4,5-methylenedioxyamphetamine ~50 mg Unknown DMMDA-3 4,5-Dimethoxy-2,3-methylenedioxyamphetamine Unknown Unknown DMMDA-4 (2,6-dimethoxy-MDA) 2,6-Dimethoxy-3,4-methylenedioxyamphetamine Unknown Unknown DMMDA-5 4,6-Dimethoxy-2,3-methylenedioxyamphetamine Unknown Unknown DMMDA-6 2,3-Dimethoxy-5,6-methylenedioxyamphetamine Unknown Unknown EMDA-2 (6-ethoxy-MDA) 2-Ethoxy-4,5-methylenedioxyamphetamine 135–185 mg 10–12 hours 6-Chloro-MDA 2-Chloro-4,5-methylenedioxyamphetamine 160 mg 8 hours 6-Bromo-MDA 2-Bromo-4,5-methylenedioxyamphetamine >350 mg Unknown 2T-MMDA-3a 2-Methylthio-3,4-methylenedioxyamphetamine >12 mg Unknown EIDA (EDA; 7-methyl-MDA) 3,4-Ethylidenedioxyamphetamine >150 mg Unknown IDA (7,7-dimethyl-MDA) 3,4-Isopropylidenedioxyamphetamine Unknown Unknown DFMDA (7,7-difluoro-MDA) 3,4-(Difluoromethylenedioxy)amphetamine ≥250 mg Unknown MDMA (Ecstasy; Molly; Adam) 3,4-Methylenedioxy-N-methylamphetamine 80–150 mg (25–200 mg+) 3–6 hours (S)-MDMA (S)-3,4-Methylenedioxy-N-methylamphetamine 60–125 mg 5 hours (R)-MDMA (R)-3,4-Methylenedioxy-N-methylamphetamine 250–300 mg 4–5 hours MDEA (MDE; Eve) 3,4-Methylenedioxy-N-ethylamphetamine 100–200 mg (30–225 mg+) 3–5 hours MDPR 3,4-Methylenedioxy-N-propylamphetamine >200 mg Unknown MDIP 3,4-Methylenedioxy-N-isopropylamphetamine >250–350 mg Unknown MDBU 3,4-Methylenedioxy-N-butylamphetamine >40 mg Unknown MDCPM 3,4-Methylenedioxy-N-cyclopropylmethylamphetamine >10 mg Unknown MDAL 3,4-Methylenedioxy-N-allylamphetamine >180 mg Unknown MDPL 3,4-Methylenedioxy-N-propargylamphetamine >150–200 mg Unknown MDBZ 3,4-Methylenedioxy-N-benzylamphetamine >150 mg Unknown MDOH 3,4-Methylenedioxy-N-hydroxyamphetamine 100–160 mg 3–6 hours MDMEO (MDME) 3,4-Methylenedioxy-N-methoxyamphetamine >180 mg Unknown MDHOET 3,4-Methylenedioxy-N-(β-hydroxyethyl)amphetamine >50 mg Unknown MDMEOET 3,4-Methylenedioxy-N-(β-methoxyethyl)amphetamine >180 mg Unknown MDTFEA (MDTFE) 3,4-Methylenedioxy-N-(2,2,2-trifluoroethyl)amphetamine >500 mg Unknown MDDM (MDDMA) 3,4-Methylenedioxy-N,N-dimethylamphetamine >150 mg Unknown FLEA (MDMOH, MDHMA) 3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine 100–160 mg 4–8 hours Lys-MDA N-(L-Lysinamidyl)-3,4-methylenedioxyamphetamine ~164 mg ~6 hours Lys-MDMA N-(L-Lysinamidyl)-3,4-methylenedioxy-N-methylamphetamine Inactiveb Inactiveb N-t-BOC-MDMA N-tert-Butoxycarbonyl-3,4-methylenedioxy-N-methylamphetamine Unknown Unknown MADAM-6 (6-methyl-MDMA) 2-Methyl-4,5-methylenedioxy-N-methylamphetamine >280 mg Unknown MMDMA (5-methoxy-MDMA) 3-Methoxy-4,5-methylenedioxy-N-methylamphetamine Unknown Unknown Methyl-MMDA-2 (6-methoxy-MDMA) 2-Methoxy-4,5-methylenedioxy-N-methylamphetamine >70 mg Unknown DFMDMA (7,7-difluoro-MDMA) 3,4-(Difluoromethylenedioxy)-N-methylamphetamine >120 mg Unknown BDB (J) 3,4-Methylenedioxy-α-ethylphenethylamine 150–230 mg 4–8 hours MBDB (methyl-J; Eden) 3,4-Methylenedioxy-N-methyl-α-ethylphenethylamine 180–210 mg (150–250 mg+) 4–6 hours Ethyl-J (EBDB) 3,4-Methylenedioxy-N-ethyl-α-ethylphenethylamine >90 mg "Short" BDP (K) 3,4-Methylenedioxy-α-propylphenethylamine Unknown Unknown Methyl-K (MBDP) 3,4-Methylenedioxy-N-methyl-α-propylphenethylamine >100 mg Unknown Ethyl-K (EBDP) 3,4-Methylenedioxy-N-ethyl-α-propylphenethylamine >40 mg Unknown MPAP (propyl-K; PDBP) 3,4-methylenedioxy-N-propyl-α-propylphenethylamine Unknown Unknown MDPH 3,4-Methylenedioxy-α,α-dimethylphenethylamine 160–240 mg 3–5 hours MDMP (MDMPH) 3,4-Methylenedioxy-N-methyl-α,α-dimethylphenethylamine >110 mg ~6 hours 3C-BOH (β-methoxy-MDA) 3,4-Methylenedioxy-β-methoxyamphetamine 40–70 mg 3–6 hours MDC (βk-MDA) 3,4-Methylenedioxy-β-ketoamphetamine Unknown Unknown Methylone (βk-MDMA) 3,4-Methylenedioxy-N-methyl-β-ketoamphetamine 100–250 mg (60–325 mg+) 2–5 hours Ethylone (βk-MDEA) 3,4-Methylenedioxy-N-ethyl-β-ketoamphetamine 150–250 mg (80–400 mg) 2–6 hours Dimethylone (βk-MDDMA) 3,4-Methylenedioxy-N,N-dimethyl-β-ketoamphetamine Unknown Unknown Butylone (βk-MBDB) 3,4-Methylenedioxy-N-methyl-α-ethyl-β-ketophenethylamine 100–250 mg (20–250 mg) 2–5 hours Eutylone (βk-EBDB) 3,4-Methylenedioxy-N-ethyl-α-ethyl-β-ketophenethylamine Unknown Unknown Putylone (βk-PBDB) 3,4-Methylenedioxy-N-propyl-α-ethyl-β-ketophenethylamine Unknown Unknown Dibutylone (βk-DMBDB) 3,4-Methylenedioxy-N,N-dimethyl-α-ethyl-β-ketophenethylamine Unknown Unknown Pentylone (βk-MBDP) 3,4-Methylenedioxy-N-methyl-α-propyl-β-ketophenethylamine 30 mg (10–80 mg) Unknown Ephylone (βk-EBDP) 3,4-Methylenedioxy-N-ethyl-α-propyl-β-ketophenethylamine Unknown Unknown Dipentylone (βk-DMBDP) 3,4-Methylenedioxy-N,N-dimethyl-α-propyl-β-ketophenethylamine Unknown Unknown Isohexylone 3,4-Methylenedioxy-N-methyl-α-isobutyl-β-ketophenethylamine Unknown Unknown N-Ethylhexylone 3,4-Methylenedioxy-N-ethyl-α-butyl-β-ketophenethylamine Unknown Unknown N-Ethylheptylone 3,4-Methylenedioxy-N-ethyl-α-pentyl-β-ketophenethylamine Unknown Unknown 5-Methoxymethylone (βk-MMDMA) 3,4-Methylenedioxy-5-methoxy-N-methyl-β-ketoamphetamine Unknown Unknown 5-Methylethylone 3,4-Methylenedioxy-5-methyl-N-ethyl-β-ketoamphetamine Unknown Unknown Benzylone 3,4-Methylenedioxy-N-benzyl-β-ketoamphetamine Unknown Unknown MDPPP 3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)propanophenone Unknown Unknown MDPBP 3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)butanophenone Unknown Unknown MDPV (MD-α-PVP; Monkey Dust) 3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)valerophenone 5–10 mg (2–25 mg+) 3–5 hours MDPHP 3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)hexanophenone Unknown Unknown MDPEP 3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)heptanophenone Unknown Unknown MDPM 3-Methyl-3′,4′-methylenedioxy-2-phenylmorpholine Unknown Unknown MDMAR Unknown Unknown MDAI (MDA-AI) 5,6-Methylenedioxy-2-aminoindane 100–200 mg (20–300 mg+) 2–5 hours MDMAI (MDMA-AI) 5,6-Methylenedioxy-N-methyl-2-aminoindane Unknown Unknown MDAT (MDA-AT) 6,7-Methylenedioxy-2-aminotetralin Unknown Unknown MDMAT (MDMA-AT) 6,7-Methylenedioxy-N-methyl-2-aminotetralin Unknown Unknown Footnotes: a = Methylenedioxyphenethylamines (MDxx compounds) variably act as psychedelics, entactogens, and/or stimulants. Examples of psychedelics include lophophine, MDA, MMDA, and MMDA-2; examples of entactogens include MDA, MDMA, MBDB, methylone, and MDAI; and examples of stimulants include ORTHO-MDA, MDPV, MDPM, and MDMAR. b = Lys-MDMA, unlike lys-MDA, is inactive, because it does not hydrolyze into and hence act as a prodrug of MDMA. Refs: Individual:

Interactions

List of substituted methylenedioxyphenethylamines