Substituted methylenedioxyphenethylamine


Substituted methylenedioxy- phenethylamines 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.
The base compound of the MDxx class is 3,4-methylenedioxyphenethylamine, and the prototypical agent of this class is 3,4-methylenedioxy-N-methylamphetamine. Other mentionables include 3,4-methylenedioxyamphetamine, 3,4-methylenedioxy-N-ethylamphetamine, N-methyl-1,3-benzodioxolylbutanamine, and 3,4-methylenedioxy-N-methylcathinone.

List of substituted methylenedioxyphenethylamines

The compounds most commonly regarded as comprising the family of MDxx derivatives include:
StructureChemical NameAbbreviationsOther NamesCAS number
3,4-MethylenedioxyphenethylamineMDPEAHomopiperonylamine1484-85-1
3,4-Methylenedioxy-N-methylphenethylamineMDMPEAHomarylamine451-77-4
4,5-Methylendioxy-3-methoxy-phenethylamineMMDPEALophophine, Homomyristicylamine23693-38-1
4,5-Methylenedioxy-3-methoxy-N-methylphenethylamineMMDMPEA
3,4-Methylenedioxy-N-phenethylamineNBOMe-MDPEA
3,4-MethylenedioxyamphetamineMDA"Sally, Sass, Sass-a-frass or Mellow Drug of America"4764-17-4
2,3-Methylenedioxyamphetamine2,3-MDA"Love"23693-17-6
3,4-Methylenedioxy-N-methylamphetamineMDMA, MDM"Molly", "Ecstasy", "Adam", etc.42542-10-9
3,4-Methylenedioxy-N-ethylamphetamineMDEA, MDE"Eve"82801-81-8
3,4-Methylenedioxy-N-propylamphetamineMDPR, MDPA74698-36-5
3,4-Methylenedioxy-N-isopropylamphetamineMDIP, MDIPR, MDIPA74698-37-6
3,4-Methylenedioxy-N-butylamphetamineMDBU, MDBA74698-38-7
3,4-Methylenedioxy-N-isobutylamphetamineMDIB, MDIBA
3,4-Methylenedioxy-N-allylamphetamineMDAL, MDAA74698-45-6
3,4-Methylenedioxy-N-benzylamphetamineMDBZ, MDBZA65033-29-6
3,4-Methylenedioxy-N-cyclopropylmethylamphetamineMDCPM, MDCPMA, MDCA22698-08-4
3,4-Methylenedioxy-N-hydroxyamphetamineMDOH, MDHA, MDH74698-47-8
3,4-Methylenedioxy-N-amphetamineMDHOET, MDHEA74698-43-4
3,4-Methylenedioxy-N-methoxyamphetamineMDMEO, MDMEOA74698-48-9
3,4-Methylenedioxy-N-amphetamineMDMEOET, MDMEA74698-44-5
3,4-Methylenedioxy-N-propargylamphetamineMDPL, MDPLA74698-46-7
3,4-Methylenedioxy-2-methylamphetamine2-Methyl-MDA691876-73-0
4,5-Methylenedioxy-3-methylamphetamine5-Methyl-MDA749191-14-8
4,5-Methylenedioxy-2-methylamphetamine6-Methyl-MDA246861-21-2
4,5-Methylenedioxy-3-methoxy-amphetamineMMDA13674-05-0
4,5-Methylenedioxy-3-methoxy-N-methylamphetamineMMDMA172518-52-4
3,4-Methylenedioxy-N,N-dimethylamphetamineMDDM, MDDMA74698-50-3
3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamineMDMOH, MDMHA, MDHMAFLEA214414-88-7
3,4-Methylenedioxy-N-ethyl-N-hydroxyamphetamineMDEOH, MDEHA, MDHEATESS, "Nextasy"
3,4-Methylenedioxy-2,5-dimethoxyamphetamineDMMDA15183-13-8
4,5-Methylenedioxy-2,3-dimethoxyamphetamineDMMDA-215183-26-3
3,4-MethylenedioxyphentermineMDPH39235-63-7
3,4-Methylenedioxy-N-methylphentermineMDMP81262-69-3
3,4-Methylenedioxycathinoneβk-MDA, MDC80535-73-5
3,4-Methylenedioxy-N-methylcathinoneβk-MDMAMethylone186028-79-5
3,4-Methylenedioxy-N-ethylcathinoneβk-MDEA, MDECEthylone1112937-64-0
3,4-Methylenedioxy-5-methyl-N-ethylcathinone5-Me-βk-MDEA5-Methylethylone1364933-82-3
1,3-BenzodioxolylbutanamineBDBJ42542-07-4
N-Methyl-1,3-benzodioxolylbutanamineMBDBMethyl-J; "Eden"135795-90-3
N-Ethyl-1,3-benzodioxolylbutanamineEBDBEthyl-J167394-39-0
β-Hydroxy-1,3-benzodioxolylbutanamineHBDB, BOH73304-06-0
β-Keto-N-methyl-1,3-benzodioxolylbutanamineβk-MBDBButylone802575-11-7
β-Keto-N,N-dimethyl-1,3-benzodioxolylbutanamineβk-DMBDBDibutylone802286-83-5
1,3-BenzodioxolylpentanamineBDPK
N-Methyl-1,3-benzodioxolylpentanamineMBDPMethyl-K952016-78-3
N-Ethyl-1,3-benzodioxolylpentanamineEBDPEthyl-K952016-47-6
2--1--N-methylethanamineα-iPr-MDMPEAUWA-104
2--1-cyclopropyl-N-methylethanamineα-cPr-MDMPEAUWA-1011350821-24-7
2--N-methyl-1-phenylethanamineα-Ph-MDMPEAUWA-001
β-Keto-N-methyl-1,3-benzodioxolylpentanamineβk-MBDP, βk-Methyl-KPentylone698963-77-8
β-Keto-N-ethyl-1,3-benzodioxolylpentanamineβk-EBDPEphylone727641-67-0

Related compounds

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 compounds where the methylenedioxyphenyl ring is retained but the phenethyl portion is modified, or 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.
StructureChemical NameAbbreviationsOther NamesCAS number
3,4-Methylenedioxyphenyl-1-propeneIsosafrole120-58-1
3,4-Methylenedioxyphenyl-2-propeneSafrole, Shikimol94-59-7
4,5-Methylenedioxyphenyl-3-methoxy-2-propeneMyristicin607-91-0
3,4-Methylenedioxyphenyl-1-propanoneMDP1P28281-49-4
3,4-Methylenedioxyphenyl-2-propanoneMDP2P4676-39-5
3,4-MethylenedioxybenzaldehydePiperonal120-57-0
3,4-MethylenedioxyphenolSesamol533-31-3
5--2,4-pentadienoyl-2-piperidinePiperine 94-62-2
3,4-MethylenedioxycinnamylpiperidineIlepcimide23434-86-8
Paroxetine|trans-4--3-methylpiperidineParoxetine61869-08-7
5,6-Methylenedioxy-2-aminoindane5,6-MDAI, MDAI132741-81-2
5,6-Methylenedioxy-N-methyl-2-aminoindane5,6-MDMAI, MDMAI132741-82-3
6,7-Methylenedioxy-2-aminotetralin6,7-MDAT101625-35-8
6,7-Methylenedioxy-2-methylaminotetralin6,7-MDMAT34620-52-5
3,4-Methylenedioxy-1-benzylpiperazineMDBZPPiperonylpiperazine32231-06-4
3,4-Methylenedioxy-α-pyrrolidinopropiophenoneMDPPP783241-66-7
3',4'-Methylenedioxy-α-pyrrolidinobutiophenoneMDPBP784985-33-7
3,4-Methylenedioxy-α-pyrrolidinopentiophenoneMDPV687603-66-3
3,4-Methylenedioxy-α-pyrrolidinohexiophenoneMDPHP776994-64-0
3-methyl-2-morpholineMDPM3,4-Methylenedioxyphenmetrazine
Methyl acetateMDMPH3,4-Methylenedioxymethylphenidate
4-Methyl-5--4,5-dihydro-1,3-oxazol-2-amineMD-4-MAR3',4'-Methylenedioxy-4-methylaminorex1445573-16-9
1--4-methyl-7,8-methylenedioxy-2,3-benzodiazepineGYKI-52895869360-93-0
3,4-EthylidenedioxyamphetamineEIDA125299-84-5
3,4-isopropylidenedioxyamphetamineIDA
1-propan-2-amineDFMDA910393-51-0
6--5-methoxy-1,3-benzoxathiol4T-MMDA-2133787-69-6
1--N-methylpropan-2-amineEDMA133787-66-3
1-propan-2-amine5-APDB152624-03-8
1--N-methylpropan-2-amineIBF5MAP201407-56-9
1-propan-2-amine6-APDB152623-93-3
1-propan-2-amine5-APB286834-81-9
N-methyl-1-propan-2-amine5-MAPB1354631-77-8
N-ethyl-1-propan-2-amine5-EAPB1445566-01-7
N-methyl-1-butan-2-amine5-MBPB
1-propan-2-amine6-APB286834-85-3
N-methyl-1-propan-2-amine6-MAPB1354631-79-0
1-propan-2-amine5-APDIIAP13396-94-6
1--N-methylpropan-2-amine5-MAPDIIMP1310153-27-5
1-propan-2-amine6-APTTAP3160-20-1
1-propan-2-amineNAPPAL-28718085-03-5
N-methyl-1-propan-2-amineMNAPMethamnetamine
1-propan-2-amine5-APBT1368128-53-3
1-propan-2-amine5-API5-IT3784-30-3
1-propan-2-amine752145-76-9
1-propan-2-amine1368557-51-0
1-propan-2-amine1896565-11-9
1-propan-2-amine910413-33-1
1-propan-2-amine1337128-11-6
1-propan-2-amine1380044-39-2
1-propan-2-amine910407-54-4