Substituted methylenedioxyphenethylamines

Substituted methylenedioxyphenethylamines

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.

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

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").

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
3,4-Methylenedioxyamphetamine MDA "Mellow Drug of America" Phenylpropylamine
2,3-Methylenedioxyamphetamine 2,3-MDA "Love" 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-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 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
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

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
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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