Substituted methylenedioxyphenethylamine


The substituted methylenedioxyphenethylamines represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational drugs.
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 notable MDxx class substances include 3,4-methylenedioxyamphetamine, 3,4-methylenedioxy-N-ethylamphetamine, N-methyl-1,3-benzodioxolylbutanamine, and 3,4-methylenedioxy-N-methylcathinone. There are also cyclized phenethylamine MDxx compounds, such as MDAI, MDAT, MDPV, MDPM, and MDMAR.

Use and effects

Interactions

List of substituted methylenedioxyphenethylamines

StructureChemical NameAbbreviationsOther NamesCAS #Ref
3,4-MethylenedioxyphenethylamineMDPEAHomopiperonylamine1484-85-1
3,4-Methylenedioxy-N-methylphenethylamineMDMPEAHomarylamine451-77-4
β,N-Dimethyl-3,4-methylenedioxyphenethylamineβ,N-DM-MDPEAMDDMPEA83329-26-4
4,5-Methylendioxy-3-methoxy-phenethylamineMMDPEALophophine, Homomyristicylamine, 2C-MMDA, 5-Methoxy-MDPEA23693-38-1
4,5-Methylenedioxy-3-methoxy-N-methylphenethylamineMMDMPEAN-Methyllophophine
2-Methoxy-4,5-methylenedioxyphenethylamine2C-MMDA-2MMDPEA-2; 6-Methoxy-MDPEA497096-69-2
2-Methoxy-3,4-methylenedioxyphenethylamine2C-MMDA-3aMMDPEA-3a; 2-Methoxy-MDPEA2220-19-1
3,4-Methylenedioxy-N-phenethylamineNBOMe-MDPEAMDPEA-NBOMe
3-Methoxy-4,5-methylenedioxy-N-phenethylamineLophophine-NBOMeMMDPEA-NBOMe; 5-Methoxy-MDPEA-NBOMe
N-(2-Methoxybenzyl)-2-methoxy-4,5-methylenedioxyphenethylamine2C2-NBOMe2C-MMDA-2-NBOMe; NBOMe-MMDPEA-2; 6-Methoxy-MDPEA-NBOMe
3,4-MethylenedioxyamphetamineMDA"Sally, Sass, Sass-a-frass or Mellow Drug of America"4764-17-4
2,3-Methylenedioxyamphetamine2,3-MDAORTHO-MDA23693-17-6
2,3-Methylenedioxymethamphetamine2,3-MDMAORTHO-MDMA168967-99-5
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-(2-hydroxyethyl)amphetamineMDHOET, MDHEA74698-43-4
3,4-Methylenedioxy-N-methoxyamphetamineMDMEO, MDMEOA74698-48-9
3,4-Methylenedioxy-N-(2-methoxyethyl)amphetamineMDMEOET, MDMEA74698-44-5
3,4-Methylenedioxy-N-propargylamphetamineMDPL, MDPLA74698-46-7
N-(L-Lysinamidyl)-3,4-methylenedioxyamphetamineLys-MDA1391487-26-5
N-(L-Lysinamidyl)-3,4-methylenedioxy-N-methylamphetamineLys-MDMA2763054-67-5
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-amphetamineMMDA5-Methoxy-MDA13674-05-0
4,5-Methylenedioxy-3-methoxy-N-methylamphetamineMMDMAN-Methyl-MMDA; 5-Methoxy-MDMA172518-52-4
2-Methoxy-4,5-methylenedioxyamphetamineMMDA-26-Methoxy-MDA23693-18-7
2-Ethoxy-4,5-methylenedioxyamphetamineEDMA-2
3,4-Methylenedioxy-N,''N-dimethylamphetamineMDDM, MDDMA74698-50-3
3,4-Methylenedioxy-N'',N,''N-trimethylamphetamineMDTMA
3,4-Methylenedioxy-N''-methyl-N-hydroxyamphetamineMDMOH, MDMHA, MDHMAFLEA214414-88-7
3,4-Methylenedioxy-N-ethyl-N-hydroxyamphetamineMDEOH, MDEHA, MDHEA866417-59-6
3,4-Methylenedioxy-2,5-dimethoxyamphetamineDMMDA15183-13-8
4,5-Methylenedioxy-2,3-dimethoxyamphetamineDMMDA-215183-26-3
2-Chloro-4,5-methylenedioxyamphetamine6-Chloro-MDA2-Cl-4,5-MDA46319-44-2
2-Chloro-4,5-methylenedioxy-N-methylamphetamine6-Chloro-MDMA2-Cl-4,5-MDMA319920-71-3
2-Bromo-4,5-methylenedioxyamphetamine6-Bromo-MDA2-Br-4,5-MDA151920-03-5
2-Bromo-4,5-methylenedioxy-N-methylamphetamine6-Bromo-MDMA2-Br-4,5-MDMA2170110-34-4
3,4-MethylenedioxyphentermineMDPH39235-63-7
3,4-Methylenedioxy-N-methylphentermineMDMP81262-69-3
3,4-Methylenedioxycathinoneβk-MDA, MDC80535-73-5
3,4-Methylenedioxy-N-methylcathinoneβk-MDMA, MDMCMethylone186028-79-5
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
3,4-Methylenedioxy-β-methoxyphenethylamineBOHβ-MeO-MDPEA73304-06-0
3,4-Methylenedioxy-β-methoxyamphetamine3C-BOHβ-MeO-MDA?
β-Keto-N-methyl-1,3-benzodioxolylbutanamineβk-MBDBButylone802575-11-7
β-Keto-N-ethyl-1,3-benzodioxolylbutanamineβk-EBDBEutylone802855-66-9
β-Keto-N,''N-dimethyl-1,3-benzodioxolylbutanamineβk-DMBDBDibutylone802286-83-5
1,3-BenzodioxolylpentanamineBDPK220491-69
N''-Methyl-1,3-benzodioxolylpentanamineMBDPMethyl-K952016-78-3
N-Ethyl-1,3-benzodioxolylpentanamineEBDPEthyl-K952016-47-6
1-(3,4-Methylenedioxyphenyl)-2-propylaminopentaneMPAPPBDP
2--1--N-methylethanamineα-iPr-MDMPEAUWA-104
2-(1,3-Benzodioxol-5-yl)-1-cyclopropyl-N-methylethanamineα-cPr-MDMPEAUWA-1011350821-24-7
2-(1,3-Benzodioxol-5-yl)-N-methyl-1-phenylethanamineα-Ph-MDMPEAUWA-0011350821-28-1
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. In addition to the and compounds, MDxx compounds are closely related to the other two main phenylethylamine classes, those being substituted amphetamines and substituted cathinones. Like amphetamines and cathinones, MDxx compounds derive most if not all of their stimulant effects from the phenylethylamine core, in fact most MDxx compounds can also be grouped with cathinones and or amphetamines due to having similar functional groups, but in most cases any compound with a methylenedioxy group attached will be grouped as an MDxx compound due to the unique hallucinogenic and empathogenic/entactogenic effects that are not present in most other amphetamines and present to a lesser extent in most cathinones.
StructureChemical NameAbbreviationsOther NamesCAS #Ref
3,4-Dimethoxyamphetamine3,4-DMA120-26-3
3,4-Dimethoxymethamphetamine3,4-DMMA33236-61-2
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-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidinePiperine 94-62-2
3,4-MethylenedioxycinnamylpiperidineIlepcimide23434-86-8
3,4-methylenedioxy-α,N-dimethylbenzylamineMDM1EAα,N-DMMDBA121734-65-4
3,4-methylenedioxy-α-ethylbenzylamineALPHA127292-42-6
3,4-methylenedioxy-α-ethyl-N-methylbenzylamineM-ALPHA127292-43-7
4-(1,3-Benzodioxol-5-yl)butan-2-amineHomo-MDA, HMDA40742-32-3
4-(1,3-Benzodioxol-5-yl)-N-methylbutan-2-amineHomo-MDMA, HMDMA108248-08-4
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-pyrrolidinopentiophenoneMDPV"Monkey Dust"687603-66-3
3,4-Methylenedioxy-α-pyrrolidinohexiophenoneMDPHPAlso known as "Monkey Dust"776994-64-0
MethylenedioxyphenmetrazineMDPM3,4-Methylenedioxyphenmetrazine
Methyl acetateMDMPH3,4-Methylenedioxymethylphenidate
4-Methyl-5-(1,3-benzodioxol-5-yl)-4,5-dihydro-1,3-oxazol-2-amineMDMAR3',4'-Methylenedioxy-4-methylaminorex1445573-16-9
1-(4-Aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepineGYKI-52895869360-93-0
3,4-EthylidenedioxyamphetamineEIDA125299-84-5
3,4-IsopropylidenedioxyamphetamineIDA
1-(2,2-Difluoro-1,3-benzodioxol-5-yl)propan-2-amineDFMDA910393-51-0
3,4-EthylenedioxyamphetamineEDAEDA-615033-67-7
3,4-Ethylenedioxy-N-methylamphetamineEDMA133787-66-3
3-Methoxy-4,5-ethylenedioxyamphetamineMEDA5-Methoxy-EDA23693-25-6
3-Methoxy-4,5-trimethylenedioxyamphetamineMTDA5-Methoxy-TDA
1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine5-APDB152624-03-8
1-(1,3-Dihydro-2-benzofuran-5-yl)-N-methylpropan-2-amineIBF5MAP201407-56-9
1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine6-APDB152623-93-3
1-(1-Benzofuran-5-yl)propan-2-amine5-APB286834-81-9
N-Methyl-1-(1-benzofuran-5-yl)propan-2-amine5-MAPB1354631-77-8
N-Ethyl-1-(1-benzofuran-5-yl)propan-2-amine5-EAPB1445566-01-7
N-Methyl-1-(1-benzofuran-5-yl)butan-2-amine5-MBPB5-MABB
1-(1-Benzofuran-6-yl)propan-2-amine6-APB286834-85-3
N-Methyl-1-(1-benzofuran-6-yl)propan-2-amine6-MAPB1354631-79-0
6-(2-Methylaminobutyl)benzofuran6-MBPB6-MABB
1-(2,3-Dihydro-1H-inden-5-yl)propan-2-amine5-APDIIAP13396-94-6
1-(2,3-Dihydro-1H-inden-5-yl)-N-methylpropan-2-amine5-MAPDIIMP1310153-27-5
1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine6-APTTAP3160-20-1
2-(Pyrrolidin-1-yl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)pentan-1-oneTH-PVP2304915-07-7
1-(Naphthalen-2-yl)propan-2-amineNAPPAL-28718085-03-5
N-Methyl-1-(naphthalen-2-yl)propan-2-amineMNAPMethamnetamine; PAL-10461178720-66-5
N-Ethyl-1-naphthalen-2-ylpropan-2-amineENAPPAL-1045
2-(Methylamino)-1-(naphthalene-2-yl) propan-1-oneBMAPNβk-Methamnetamine; 2-Naphthylmethcathinone109453-73-8
1-(1-Benzothiophen-5-yl)propan-2-amine5-APBT1368128-53-3
5-MAPBT|1--N-methylpropan-2-amine5-MAPBTMY4002613382-32-2
1-(1-Benzothiophen-6-yl)propan-2-amine6-APBT
6-MAPBT|1--N-methylpropan-2-amine6-MAPBTMY300
1-(1-Benzothiophen-5-yl)-2-(methylamino)propan-1-oneBK-5-MAPBT2106849-09-4
1-(1H-Indol-5-yl)propan-2-amine5-API5-IT3784-30-3
1-propan-2-amine752145-76-9
1--N-methylpropan-2-amine
1-propan-2-amine1368557-51-0
1-propan-2-amine5-BZT-MDA
1--N-methylpropan-2-amine5-BZT-MDMA
1-propan-2-amine6-BZT-MDA1896565-11-9
1--N-methylpropan-2-amine6-BZT-MDMA
1-propan-2-amineSDA; 3T-MDA
1--N-methylpropan-2-amineSDMA; 3T-MDMAMY100
1--N,''N-dimethylpropan-2-amineMY101
1--N''-methylpropan-2-amineMY200
6-(2-Aminopropyl)-5-methoxy-1,3-benzoxathiol4T-MMDA-2133787-69-6
1-propan-2-amine1337128-11-6
1-propan-2-amine1380044-39-2
1-propan-2-amine910407-54-4
1-propan-2-amine910413-33-1
1-(2,1,3-Benzoxadiazol-5-yl)-N-methylpropan-2-amineODMA2567501-96-4
1-(2,1,3-Benzothiadiazol-5-yl)-N-methylpropan-2-amineTDMA2302389-87-1
1-(2,1,3-Benzoselenadiazol-5-yl)-N-methylpropan-2-amineSeDMA