Substituted methylenedioxyphenethylamine

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.

Methylenedioxyphenethylamine (MDPEA)

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").

List of substituted methylenedioxyphenethylamines

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

Chemical Name Abbreviations Other Names Chemical Class
3,4-MethylenedioxyphenethylamineMDPEAHomopiperonylaminePhenylethylamine
3,4-Methylenedioxy-N-methylphenethylamineMDMPEAHomarylaminePhenylethylamine
4,5-Methylendioxy-3-methoxy-phenethylamineMMDPEALophophine, HomomyristicylaminePhenylethylamine
4,5-Methylenedioxy-3-methoxy-N-methylphenethylamineMMDMPEAPhenylethylamine
3,4-MethylenedioxyamphetamineMDA"Sally, Sass, Sass-a-frass or Mellow Drug of America"Phenylpropylamine
2,3-Methylenedioxyamphetamine2,3-MDA"Love"Phenylpropylamine
3,4-Methylenedioxy-N-methylamphetamineMDMA, MDM"Molly", "Ecstasy", "Adam", etc.Phenylpropylamine
3,4-Methylenedioxy-N-ethylamphetamineMDEA, MDE"Eve"Phenylpropylamine
3,4-Methylenedioxy-N-propylamphetamineMDPR, MDPAPhenylpropylamine
3,4-Methylenedioxy-N-isopropylamphetamineMDIP, MDIPR, MDIPAPhenylpropylamine
3,4-Methylenedioxy-N-butylamphetamineMDBU, MDBAPhenylpropylamine
3,4-Methylenedioxy-N-isobutylamphetamineMDIB, MDIBAPhenylpropylamine
3,4-Methylenedioxy-N-allylamphetamineMDAL, MDAAPhenylpropylamine
3,4-Methylenedioxy-N-benzylamphetamineMDBZ, MDBZAPhenylpropylamine
3,4-Methylenedioxy-N-cyclopropylmethylamphetamineMDCPM, MDCPMA, MDCAPhenylpropylamine
3,4-Methylenedioxy-N-hydroxyamphetamineMDOH, MDHA, MDHPhenylpropylamine
3,4-Methylenedioxy-N-(2-hydroxyethyl)amphetamineMDHOET, MDHEAPhenylpropylamine
3,4-Methylenedioxy-N-methoxyamphetamineMDMEO, MDMEOAPhenylpropylamine
3,4-Methylenedioxy-N-(2-methoxyethyl)amphetamineMDMEOET, MDMEAPhenylpropylamine
3,4-Methylenedioxy-N-propargylamphetamineMDPL, MDPLAPhenylpropylamine
3,4-Methylenedioxy-2-methylamphetamine2-Methyl-MDAPhenylpropylamine
4,5-Methylenedioxy-3-methylamphetamine5-Methyl-MDAPhenylpropylamine
4,5-Methylenedioxy-2-methylamphetamine6-Methyl-MDAPhenylpropylamine
4,5-Methylenedioxy-3-methoxy-amphetamineMMDAPhenylpropylamine
4,5-Methylenedioxy-3-methoxy-N-methylamphetamineMMDMAPhenylpropylamine
3,4-Methylenedioxy-N,N-dimethylamphetamineMDDM, MDDMAPhenylpropylamine
3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamineMDMOH, MDMHA, MDHMAFLEAPhenylpropylamine
3,4-Methylenedioxy-N-ethyl-N-hydroxyamphetamineMDEOH, MDEHA, MDHEATESS, "Nextasy"Phenylpropylamine
3,4-Methylenedioxy-2,5-dimethoxyamphetamineDMMDAPhenylpropylamine
4,5-Methylenedioxy-2,3-dimethoxyamphetamineDMMDA-2Phenylpropylamine
3,4-MethylenedioxyphentermineMDPHPhenylpropylamine
3,4-Methylenedioxy-N-methylphentermineMDMP, MDMPHPhenylpropylamine
3,4-Methylenedioxycathinonebk-MDA, MDCPhenylpropylamine
3,4-Methylenedioxy-N-methylcathinonebk-MDMAMethylonePhenylpropylamine
3,4-Methylenedioxy-N-ethylcathinonebk-MDEA, MDECEthylonePhenylpropylamine
1,3-BenzodioxolylbutanamineBDBJPhenylbutylamine
N-Methyl-1,3-benzodioxolylbutanamineMBDBMethyl-J; "Eden"Phenylbutylamine
N-Ethyl-1,3-benzodioxolylbutanamineEBDBEthyl-JPhenylbutylamine
β-Hydroxy-1,3-benzodioxolylbutanamineHBDB, BOHHydroxy-JPhenylbutylamine
β-Keto-N-methyl-1,3-benzodioxolylbutanaminebk-MBDBButylonePhenylbutylamine
β-Keto-N,N-dimethyl-1,3-benzodioxolylbutanaminebk-DMBDBDibutylonePhenylbutylamine
1,3-BenzodioxolylpentanamineBDPKPhenylpentylamine
N-Methyl-1,3-benzodioxolylpentanamineMBDPMethyl-KPhenylpentylamine
N-Ethyl-1,3-benzodioxolylpentanamineEBDPEthyl-KPhenylpentylamine
β-Keto-N-methyl-1,3-benzodioxolylpentanaminebk-MBDP, bk-Methyl-KPentylonePhenylpentylamine

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-propeneIsosafrolePhenylpropene
3,4-Methylenedioxyphenyl-2-propeneSafrole, ShikimolPhenylpropene
4,5-Methylenedioxyphenyl-3-methoxy-2-propeneMyristicinPhenylpropene
3,4-Methylenedioxyphenyl-1-propanoneMDP1PPhenylpropanone
3,4-Methylenedioxyphenyl-2-propanoneMDP2PPhenylpropanone
5,6-Methylenedioxy-2-aminoindane5,6-MDAI, MDAIAminoindane
5,6-Methylenedioxy-N-methyl-2-aminoindane5,6-MDMAI, MDMAIAminoindane
6,7-Methylenedioxy-2-aminotetralin6,7-MDATAminotetralin
3,4-MethylenedioxybenzaldehydePiperonalBenzaldehyde
3,4-MethylenedioxyphenolSesamolPhenols
5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidinePiperine (also chavicine)Piperidine
3,4-MethylenedioxycinnamylpiperidineIlepcimidePiperidine
trans-4-(4-Fluorophenyl)-3-[(3,4-methylenedioxy)phenoxy]methylpiperidineParoxetinePiperidine
3,4-Methylenedioxy-1-benzylpiperazineMDBZPPiperonylpiperazinePiperazine
3,4-Methylenedioxy-1-benzyl chlorideMDBZCPiperonyl chlorideBenzyl halide
3,4-Methylenedioxy-α-pyrrolidinopropiophenoneMDPPPPyrrolidinoalkylphenone
3',4'-Methylenedioxy-α-pyrrolidinobutiophenoneMDPBPPyrrolidinoalkylphenone
1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepineGYKI-528952,3-Benzodiazepine

See also
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