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.[1]

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 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 (βk-MDMA; "Methylone").

List of substituted methylenedioxyphenethylamines

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

Structure Chemical Name Abbreviations Other Names CAS number
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-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-(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-MDA[2]1391487-26-5
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-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-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-BenzodioxolylpentanamineBDPK
N-Methyl-1,3-benzodioxolylpentanamineMBDPMethyl-K952016-78-3
N-Ethyl-1,3-benzodioxolylpentanamineEBDPEthyl-K952016-47-6
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-001
β-Keto-N-methyl-1,3-benzodioxolylpentanamineβk-MBDP, βk-Methyl-KPentylone698963-77-8
β-Keto-N-ethyl-1,3-benzodioxolylpentanamineβk-EBDPEphylone727641-67-0

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.

Structure Chemical Name Abbreviations Other Names CAS 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-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidinePiperine (also chavicine)94-62-2
3,4-MethylenedioxycinnamylpiperidineIlepcimide23434-86-8
trans-4-(4-Fluorophenyl)-3-[(3,4-methylenedioxy)phenoxy]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
MethylenedioxyphenmetrazineMDPM3,4-Methylenedioxyphenmetrazine[3]
Methyl (1,3-benzodioxol-5-yl)(piperidin-2-yl)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
6-(2-aminopropyl)-5-methoxy-1,3-benzoxathiol4T-MMDA-2133787-69-6
1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-methylpropan-2-amineEDMA133787-66-3
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-MBPB
1-(1-benzofuran-6-yl)propan-2-amine6-APB286834-85-3
N-methyl-1-(1-benzofuran-6-yl)propan-2-amine6-MAPB1354631-79-0
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
1-(naphthalen-2-yl)propan-2-amineNAPPAL-28718085-03-5
N-methyl-1-(naphthalen-2-yl)propan-2-amineMNAPMethamnetamine
1-(1-benzothiophen-5-yl)propan-2-amine5-APBT1368128-53-3
1-(1H-indol-5-yl)propan-2-amine5-API5-IT3784-30-3
1-(1H-1,3-benzodiazol-5-yl)propan-2-amine752145-76-9
1-(1,3-benzoxazol-5-yl)propan-2-amine1368557-51-0
1-(1,3-benzothiazol-6-yl)propan-2-amine1896565-11-9
1-(2,1,3-benzoxadiazol-5-yl)propan-2-amine910413-33-1
1-{imidazo[1,2-a]pyridin-6-yl}propan-2-amine1337128-11-6
1-(1,2,3-benzothiadiazol-5-yl)propan-2-amine1380044-39-2
1-(quinoxalin-6-yl)propan-2-amine910407-54-4

See also

References
  1. Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  2. Liechti ME, et al. Mdma prodrugs to assist psychotherapy. Patent WO 2022/106947
  3. Świst M, Wilamowski J, Zuba D, Kochana J, Parczewski A (May 2005). "Determination of synthesis route of 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P) based on impurity profiles of MDMA". Forensic Science International. 149 (2–3): 181–92. doi:10.1016/j.forsciint.2004.06.016. PMID 15749360.
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