Thesubstituted methylenedioxyphenethylamines (abbreviated asMDxx) represent a diverse chemical class of compounds derived fromphenethylamines. This category encompasses numerouspsychoactive substances withentactogenic,psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application asresearch chemicals,designer drugs, and recreational substances.[1]
The basecompound of the MDxx class is3,4-methylenedioxyphenethylamine (MDPEA), and the prototypical agent of this class is3,4-methylenedioxy-N-methylamphetamine (MDMA; "ecstasy"). Other notable MDxx class substances include3,4-methylenedioxyamphetamine (MDA),3,4-methylenedioxy-N-ethylamphetamine (MDEA; "Eve"),N-methyl-1,3-benzodioxolylbutanamine (MBDB; "Eden"), and3,4-methylenedioxy-N-methylcathinone (βk-MDMA; "Methylone"). There are alsocyclized phenethylamines MDxx compounds, such asMDAI,MDAT,MDPV,MDPM, andMDMAR.
| 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 | |
| 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 | 3′,4′-Methylenedioxy-4-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine | 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 aspsychedelics,entactogens, and/orstimulants. Examples of psychedelics includelophophine,MDA,MMDA, andMMDA-2; examples of entactogens includeMDA,MDMA,MBDB,methylone, andMDAI; and examples of stimulants includeORTHO-MDA,MDPV,MDPM, andMDMAR.b =Lys-MDMA, unlikelys-MDA, is inactive, because it does nothydrolyze into and hence act as aprodrug of MDMA.Refs:[2][1][3][4][5][6][7][8][9][10][11]Individual:[12][13][14][15][16][17][18][19] | ||||
In addition, there are a number of other compounds that have some structural and pharmacological similarities to the methylenedioxyphenethylamines, and are useful for comparison. 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. In addition to the (i) and (ii) compounds, MDxx compounds are closely related to the other two main phenylethylamine classes, those beingsubstituted amphetamines andsubstituted cathinones. Like amphetamines and cathinones, MDxx compounds derive most if not all of their stimulant effects from thephenylethylamine core, in fact most MDxx compounds can also be grouped with cathinones and or amphetamines due to having similar functional groups, but in most cases any compound with amethylenedioxy group attached will be grouped as an MDxx compound due to the unique hallucinogenic and empathogenic/entactogenic effects that are not present in most other amphetamines and present to a lesser extent in most cathinones.
Doses range from 70–300 mg; typical doses appear to be 150–200 mg of active ingredient (equivalent to half of a 300 mg capsule or a whole 200 mg capsule). A 'low' dose of 70–80 mg produces subtle but noticeable effects; a strong dose is considered to be 250–300 mg. Redosing often occurs; typically a 'booster' of 100–150 mg is administered after the initial positive effects have worn off (Drugs-Forum, 2009a; Bluelight, 2010a; Herbalhighs, 2012a; Partyvibe, 2012).
Table 2 Dosage, Onset, and Duration of Action of Psychostimulatory NPS [...] Compound: Mephedrone. Doses: [...] 150–250 mg orally [...] Duration: 2–4 h [...] Compound: MDPV. [...] Doses: 3–15 mg (typically 5–10 mg). [...] Duration: [...] up to 7 h (oral) [...] Compound: MDAI. [...] Doses: 70–300 mg. [...]
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