Substituted methylenedioxyphenethylamine

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Substituted methylenedioxyphenethylamine

The substituted methylenedioxyphenethylamines (abbreviated as MDxx) 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 substances.[1]

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Methylenedioxyphenethylamine (MDPEA)

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 notable MDxx class substances 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 (βk-MDMA; "Methylone").

List of substituted methylenedioxyphenethylamines

Summarize
Perspective

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

More information Structure, Chemical Name ...
Structure Chemical Name Abbreviations Other Names CAS number 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, Homomyristicylamine23693-38-1
4,5-Methylenedioxy-3-methoxy-N-methylphenethylamineMMDMPEA
3,4-Methylenedioxy-N-(2-methoxybenzyl)phenethylamineNBOMe-MDPEA
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[2]
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-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,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
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
β-Methoxy-1,3-benzodioxolylbutanamineBOH73304-06-0
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-(1,3-Benzodioxol-5-yl)-1-(propan-2-yl)-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
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Summarize
Perspective

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 (i) compounds where the methylenedioxyphenyl ring is retained but the phenethyl portion is modified, or (ii) 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 (i) and (ii) 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.

More information Structure, Chemical Name ...
Structure Chemical Name Abbreviations Other Names CAS number Ref
Thumb3,4-Dimethoxyamphetamine3,4-DMA120-26-3
Thumb3,4-Dimethoxymethamphetamine3,4-DMMA33236-61-2
Thumb3,4-Methylenedioxyphenyl-1-propeneIsosafrole120-58-1
Thumb3,4-Methylenedioxyphenyl-2-propeneSafrole, Shikimol94-59-7
Thumb4,5-Methylenedioxyphenyl-3-methoxy-2-propeneMyristicin607-91-0
Thumb3,4-Methylenedioxyphenyl-1-propanoneMDP1P28281-49-4
Thumb3,4-Methylenedioxyphenyl-2-propanoneMDP2P4676-39-5
Thumb3,4-MethylenedioxybenzaldehydePiperonal120-57-0
Thumb3,4-MethylenedioxyphenolSesamol533-31-3
Thumb5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidinePiperine (also chavicine)94-62-2
Thumb3,4-MethylenedioxycinnamylpiperidineIlepcimide23434-86-8
Thumb1-(1,3-Benzodioxol-5-yl)-N-methylethanamineMDM1EAα,N-DMMDBA121734-65-4
Thumb4-(1,3-Benzodioxol-5-yl)butan-2-amineHomo-MDA, HMDA40742-32-3
Thumb4-(1,3-Benzodioxol-5-yl)-N-methylbutan-2-amineHomo-MDMA, HMDMA108248-08-4
Thumbtrans-4-(4-Fluorophenyl)-3-[(3,4-methylenedioxy)phenoxy]methylpiperidineParoxetine61869-08-7
Thumb5,6-Methylenedioxy-2-aminoindane5,6-MDAI, MDAI132741-81-2
Thumb5,6-Methylenedioxy-N-methyl-2-aminoindane5,6-MDMAI, MDMAI132741-82-3
Thumb6,7-Methylenedioxy-2-aminotetralin6,7-MDAT101625-35-8
Thumb6,7-Methylenedioxy-2-methylaminotetralin6,7-MDMAT34620-52-5
Thumb3,4-Methylenedioxy-1-benzylpiperazineMDBZPPiperonylpiperazine32231-06-4
Thumb3,4-Methylenedioxy-α-pyrrolidinopropiophenoneMDPPP783241-66-7
Thumb3',4'-Methylenedioxy-α-pyrrolidinobutiophenoneMDPBP784985-33-7
Thumb3,4-Methylenedioxy-α-pyrrolidinopentiophenoneMDPV"Monkey Dust"687603-66-3
Thumb3,4-Methylenedioxy-α-pyrrolidinohexiophenoneMDPHPAlso known as "Monkey Dust"776994-64-0
ThumbMethylenedioxyphenmetrazineMDPM3,4-Methylenedioxyphenmetrazine[3]
ThumbMethyl (1,3-benzodioxol-5-yl)(piperidin-2-yl)acetateMDMPH3,4-Methylenedioxymethylphenidate
Thumb4-Methyl-5-(1,3-benzodioxol-5-yl)-4,5-dihydro-1,3-oxazol-2-amineMDMAR3',4'-Methylenedioxy-4-methylaminorex1445573-16-9
Thumb1-(4-Aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepineGYKI-52895869360-93-0
Thumb3,4-EthylidenedioxyamphetamineEIDA125299-84-5
Thumb3,4-IsopropylidenedioxyamphetamineIDA
Thumb1-(2,2-Difluoro-1,3-benzodioxol-5-yl)propan-2-amineDFMDA910393-51-0
Thumb6-(2-Aminopropyl)-5-methoxy-1,3-benzoxathiol4T-MMDA-2133787-69-6
Thumb3,4-EthylenedioxyamphetamineEDAEDA-615033-67-7
Thumb3,4-Ethylenedioxy-N-methylamphetamineEDMA133787-66-3
Thumb1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine5-APDB152624-03-8
Thumb1-(1,3-Dihydro-2-benzofuran-5-yl)-N-methylpropan-2-amineIBF5MAP201407-56-9
Thumb1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine6-APDB152623-93-3
Thumb1-(1-Benzofuran-5-yl)propan-2-amine5-APB286834-81-9
ThumbN-Methyl-1-(1-benzofuran-5-yl)propan-2-amine5-MAPB1354631-77-8
ThumbN-Ethyl-1-(1-benzofuran-5-yl)propan-2-amine5-EAPB1445566-01-7
ThumbN-Methyl-1-(1-benzofuran-5-yl)butan-2-amine5-MBPB5-MABB
Thumb1-(1-Benzofuran-6-yl)propan-2-amine6-APB286834-85-3
ThumbN-Methyl-1-(1-benzofuran-6-yl)propan-2-amine6-MAPB1354631-79-0
Thumb6-(2-Methylaminobutyl)benzofuran6-MBPB6-MABB
Thumb1-(2,3-Dihydro-1H-inden-5-yl)propan-2-amine5-APDIIAP13396-94-6
Thumb1-(2,3-Dihydro-1H-inden-5-yl)-N-methylpropan-2-amine5-MAPDIIMP1310153-27-5
Thumb1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine6-APTTAP3160-20-1
Thumb2-(Pyrrolidin-1-yl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)pentan-1-oneTH-PVP2304915-07-7
Thumb1-(Naphthalen-2-yl)propan-2-amineNAPPAL-28718085-03-5
ThumbN-Methyl-1-(naphthalen-2-yl)propan-2-amineMNAPMethamnetamine; PAL-10461178720-66-5
ThumbN-Ethyl-1-naphthalen-2-ylpropan-2-amineENAPPAL-1045
Thumb2-(Methylamino)-1-(naphthalene-2-yl) propan-1-oneBMAPNβk-Methamnetamine; 2-Naphthylmethcathinone109453-73-8
Thumb1-(1-Benzothiophen-5-yl)propan-2-amine5-APBT1368128-53-3
Thumb1-(Benzo[b]thiophen-5-yl)-N-methylpropan-2-amine5-MAPBTMY4002613382-32-2[4][5]
Thumb1-(1-Benzothiophen-6-yl)propan-2-amine6-APBT
Thumb1-(Benzo[b]thiophen-6-yl)-N-methylpropan-2-amine6-MAPBTMY300[4][6]
Thumb1-(1H-Indol-5-yl)propan-2-amine5-API5-IT3784-30-3
Thumb1-(1H-1,3-Benzodiazol-5-yl)propan-2-amine752145-76-9
Thumb1-(1,3-Benzodiazol-5-yl)-N-methylpropan-2-amine
Thumb1-(1,3-Benzoxazol-5-yl)propan-2-amine1368557-51-0
Thumb1-(1,3-Benzothiazol-5-yl)propan-2-amine5-BZT-MDA
Thumb1-(Benzo[d]thiazol-5-yl)-N-methylpropan-2-amine5-BZT-MDMA[7][8]
Thumb1-(1,3-Benzothiazol-6-yl)propan-2-amine6-BZT-MDA1896565-11-9
Thumb1-(Benzo[d]thiazol-6-yl)-N-methylpropan-2-amine6-BZT-MDMA[7][9]
Thumb1-(Benzo[d][1,3]oxathiol-5-yl)-N-methylpropan-2-amineMY100[4][10]
Thumb1-(Benzo[d][1,3]oxathiol-5-yl)-N,N-dimethylpropan-2-amineMY101[4][11]
Thumb1-(Benzo[d][1,3]oxathiol-6-yl)-N-methylpropan-2-amineMY200[4][12]
Thumb1-(Imidazo[1,2-a]pyridin-6-yl)propan-2-amine1337128-11-6
Thumb1-(1,2,3-Benzothiadiazol-5-yl)propan-2-amine1380044-39-2
Thumb1-(Quinoxalin-6-yl)propan-2-amine910407-54-4
Thumb1-(2,1,3-Benzoxadiazol-5-yl)propan-2-amine910413-33-1
Thumb1-(2,1,3-Benzoxadiazol-5-yl)-N-methylpropan-2-amineODMA2567501-96-4
Thumb1-(2,1,3-Benzothiadiazol-5-yl)-N-methylpropan-2-amineTDMA2302389-87-1
Thumb1-(2,1,3-Benzoselenadiazol-5-yl)-N-methylpropan-2-amineSeDMA
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