Substituted methylenedioxyphenethylamines

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Substituted methylenedioxy- phenethylamines (MDxx) are a large chemical class of derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelics, and/or stimulants, as well as entheogens. These agents are used as research chemicals, designer drugs and as recreational substances.

When referring to MDMA and its counterparts, the term 'MDxx' is often used with the exception of MDPV.[citation needed]

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 mentionables 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 (bk-MDMA; "Methylone").

Chemical Derivatives[edit]

The compounds most commonly regarded as comprising the family of MDxx derivatives include:

Chemical Name Abbreviations Other Names Chemical Class
3,4-Methylenedioxyphenethylamine MDPEA Homopiperonylamine Phenylethylamine
3,4-Methylenedioxy-N-methylphenethylamine MDMPEA Homarylamine Phenylethylamine
4,5-Methylendioxy-3-methoxy-phenethylamine MMDPEA Lophophine, Homomyristicylamine Phenylethylamine
4,5-Methylenedioxy-3-methoxy-N-methylphenethylamine MMDMPEA Phenylethylamine
3,4-Methylenedioxyamphetamine MDA "Sally, Sass, Sass-a-frass or Mellow Drug of America" Phenylpropylamine
2,3-Methylenedioxyamphetamine 2,3-MDA "Love" Phenylpropylamine
3,4-Methylenedioxy-N-methylamphetamine MDMA, MDM "Molly", "Ecstasy", "Adam", etc. Phenylpropylamine
3,4-Methylenedioxy-N-ethylamphetamine MDEA, MDE "Eve" Phenylpropylamine
3,4-Methylenedioxy-N-propylamphetamine MDPR, MDPA Phenylpropylamine
3,4-Methylenedioxy-N-isopropylamphetamine MDIP, MDIPR, MDIPA Phenylpropylamine
3,4-Methylenedioxy-N-butylamphetamine MDBU, MDBA Phenylpropylamine
3,4-Methylenedioxy-N-isobutylamphetamine MDIB, MDIBA Phenylpropylamine
3,4-Methylenedioxy-N-allylamphetamine MDAL, MDAA Phenylpropylamine
3,4-Methylenedioxy-N-benzylamphetamine MDBZ, MDBZA Phenylpropylamine
3,4-Methylenedioxy-N-cyclopropylmethylamphetamine MDCPM, MDCPMA, MDCA Phenylpropylamine
3,4-Methylenedioxy-N-hydroxyamphetamine MDOH, MDHA, MDH Phenylpropylamine
3,4-Methylenedioxy-N-(2-hydroxyethyl)amphetamine MDHOET, MDHEA Phenylpropylamine
3,4-Methylenedioxy-N-methoxyamphetamine MDMEO, MDMEOA Phenylpropylamine
3,4-Methylenedioxy-N-(2-methoxyethyl)amphetamine MDMEOET, MDMEA Phenylpropylamine
3,4-Methylenedioxy-N-propargylamphetamine MDPL, MDPLA Phenylpropylamine
3,4-Methylenedioxy-2-methylamphetamine 2-Methyl-MDA Phenylpropylamine
4,5-Methylenedioxy-3-methylamphetamine 5-Methyl-MDA Phenylpropylamine
4,5-Methylenedioxy-2-methylamphetamine 6-Methyl-MDA Phenylpropylamine
4,5-Methylenedioxy-3-methoxy-amphetamine MMDA Phenylpropylamine
4,5-Methylenedioxy-3-methoxy-N-methylamphetamine MMDMA Phenylpropylamine
3,4-Methylenedioxy-N,N-dimethylamphetamine MDDM, MDDMA Phenylpropylamine
3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine MDMOH, MDMHA, MDHMA FLEA Phenylpropylamine
3,4-Methylenedioxy-N-ethyl-N-hydroxyamphetamine MDEOH, MDEHA, MDHEA TESS, "Nextasy" Phenylpropylamine
3,4-Methylenedioxy-2,5-dimethoxyamphetamine DMMDA Phenylpropylamine
4,5-Methylenedioxy-2,3-dimethoxyamphetamine DMMDA-2 Phenylpropylamine
3,4-Methylenedioxyphentermine MDPH Phenylpropylamine
3,4-Methylenedioxy-N-methylphentermine MDMP, MDMPH Phenylpropylamine
3,4-Methylenedioxycathinone bk-MDA, MDC Phenylpropylamine
3,4-Methylenedioxy-N-methylcathinone bk-MDMA Methylone Phenylpropylamine
3,4-Methylenedioxy-N-ethylcathinone bk-MDEA, MDEC Ethylone Phenylpropylamine
1,3-Benzodioxolylbutanamine BDB J Phenylbutylamine
N-Methyl-1,3-benzodioxolylbutanamine MBDB Methyl-J; "Eden" Phenylbutylamine
N-Ethyl-1,3-benzodioxolylbutanamine EBDB Ethyl-J Phenylbutylamine
β-Hydroxy-1,3-benzodioxolylbutanamine HBDB, BOH Hydroxy-J Phenylbutylamine
β-Keto-N-methyl-1,3-benzodioxolylbutanamine bk-MBDB Butylone Phenylbutylamine
β-Keto-N,N-dimethyl-1,3-benzodioxolylbutanamine bk-DMBDB Dibutylone Phenylbutylamine
1,3-Benzodioxolylpentanamine BDP K Phenylpentylamine
N-Methyl-1,3-benzodioxolylpentanamine MBDP Methyl-K Phenylpentylamine
N-Ethyl-1,3-benzodioxolylpentanamine EBDP Ethyl-K Phenylpentylamine
β-Keto-N-methyl-1,3-benzodioxolylpentanamine bk-MBDP, bk-Methyl-K Pentylone Phenylpentylamine

In addition, there are a number of other compounds that, while in the technical sense not phenethylamine derivatives, still have some structural and pharmacological similarities to the methylenedioxyphenethylamines. This makes them useful for comparison.

Chemical Name Abbreviations Other Names Chemical Class
3,4-Methylenedioxyphenyl-1-propene Isosafrole Phenylpropene
3,4-Methylenedioxyphenyl-2-propene Safrole, Shikimol Phenylpropene
4,5-Methylenedioxyphenyl-3-methoxy-2-propene Myristicin Phenylpropene
3,4-Methylenedioxyphenyl-1-propanone MDP1P Phenylpropanone
3,4-Methylenedioxyphenyl-2-propanone MDP2P Phenylpropanone
5,6-Methylenedioxy-2-aminoindane 5,6-MDAI, MDAI Aminoindane
5,6-Methylenedioxy-N-methyl-2-aminoindane 5,6-MDMAI, MDMAI Aminoindane
6,7-Methylenedioxy-2-aminotetralin 6,7-MDAT Aminotetralin
3,4-Methylenedioxybenzaldehyde Piperonal Benzaldehyde
3,4-Methylenedioxyphenol Sesamol Phenols
5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine Piperine (also chavicine) Piperidine
3,4-Methylenedioxycinnamylpiperidine Ilepcimide Piperidine
trans-4-(4-Fluorophenyl)-3-[(3,4-methylenedioxy)phenoxy]methylpiperidine Paroxetine Piperidine
3,4-Methylenedioxy-1-benzylpiperazine MDBZP Piperonylpiperazine Piperazine
3,4-Methylenedioxy-1-benzyl chloride MDBZC Piperonyl chloride Benzyl halide
3,4-Methylenedioxy-α-pyrrolidinopropiophenone MDPPP Pyrrolidinoalkylphenone
3',4'-Methylenedioxy-α-pyrrolidinobutiophenone MDPBP Pyrrolidinoalkylphenone
1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepine GYKI-52895 2,3-Benzodiazepine

See also[edit]

References[edit]

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