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Substituted methylenedioxyphenethylamine: Wikis

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Substituted methylenedioxy- phenethylamines (MDxx) make up 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, and are used as research chemicals or designer drugs and as recreational substances.

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 (MDMC; "Methylone").

Contents

Chemical Derivatives

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 "Mellow Drug of America" Phenylpropylamine
2,3-Methylenedioxyamphetamine 2,3-MDA Phenylpropylamine
3,4-Methylenedioxy-N-methylamphetamine MDMA, MDM "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 FLEA 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, MDMC 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

Additionally, there are a number of other compounds which while technically not phenethylamine derivatives, still have some structural and pharmacological similarities to the methylenedioxyphenethylamines, which 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
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-α-pyrrolidinopropiophenone MDPPP Pyrrolidinoalkylphenone
3',4'-Methylenedioxy-α-pyrrolidinobutiophenone MDPBP Pyrrolidinoalkylphenone
3,4-Methylenedioxy-α-pyrrolidinopentiophenone MDPV "Sonic", "Magic", "Monkey Dust" Pyrrolidinoalkylphenone
1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepine GYKI-52895 2,3-Benzodiazepine

See also

References

External links

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