Substituted methylenedioxyphenethylamine

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Methylenedioxyphenethylamine
(MDPEA)

The substituted methylenedioxyphenethylamines (abbreviated as MDxx) represent a diverse chemical class of compounds derived from

designer drugs, and recreational substances.[1]

The base

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-Methylenedioxyphenethylamine
MDPEA Homopiperonylamine 1484-85-1
3,4-Methylenedioxy-N-methylphenethylamine
MDMPEA Homarylamine 451-77-4
β,N-Dimethyl-3,4-methylenedioxyphenethylamine β,N-DM-MDPEA MDDMPEA 83329-26-4
4,5-Methylendioxy-3-methoxy-phenethylamine
MMDPEA Lophophine, Homomyristicylamine 23693-38-1
4,5-Methylenedioxy-3-methoxy-N-methylphenethylamine MMDMPEA
3,4-Methylenedioxy-N-(2-methoxybenzyl)phenethylamine NBOMe-MDPEA
3,4-Methylenedioxyamphetamine MDA "Sally, Sass, Sass-a-frass or Mellow Drug of America" 4764-17-4
2,3-Methylenedioxyamphetamine 2,3-MDA "Love" 23693-17-6
3,4-Methylenedioxy-N-methylamphetamine
MDMA, MDM "Molly", "Ecstasy", "Adam", etc. 42542-10-9
3,4-Methylenedioxy-N-ethylamphetamine
MDEA, MDE "Eve" 82801-81-8
3,4-Methylenedioxy-N-propylamphetamine
MDPR, MDPA 74698-36-5
3,4-Methylenedioxy-N-isopropylamphetamine
MDIP, MDIPR, MDIPA 74698-37-6
3,4-Methylenedioxy-N-butylamphetamine MDBU, MDBA 74698-38-7
3,4-Methylenedioxy-N-isobutylamphetamine MDIB, MDIBA
3,4-Methylenedioxy-N-allylamphetamine MDAL, MDAA 74698-45-6
3,4-Methylenedioxy-N-benzylamphetamine MDBZ, MDBZA 65033-29-6
3,4-Methylenedioxy-N-cyclopropylmethylamphetamine MDCPM, MDCPMA, MDCA 22698-08-4
3,4-Methylenedioxy-N-hydroxyamphetamine
MDOH, MDHA, MDH 74698-47-8
3,4-Methylenedioxy-N-(2-hydroxyethyl)amphetamine MDHOET, MDHEA 74698-43-4
3,4-Methylenedioxy-N-methoxyamphetamine
MDMEO, MDMEOA 74698-48-9
3,4-Methylenedioxy-N-(2-methoxyethyl)amphetamine MDMEOET, MDMEA 74698-44-5
3,4-Methylenedioxy-N-propargylamphetamine
MDPL, MDPLA 74698-46-7
N-(L-lysinamidyl)-3,4-methylenedioxyamphetamine Lys-MDA[2] 1391487-26-5
3,4-Methylenedioxy-2-methylamphetamine
2-Methyl-MDA 691876-73-0
4,5-Methylenedioxy-3-methylamphetamine
5-Methyl-MDA 749191-14-8
4,5-Methylenedioxy-2-methylamphetamine
6-Methyl-MDA 246861-21-2
4,5-Methylenedioxy-3-methoxy-amphetamine
MMDA 13674-05-0
4,5-Methylenedioxy-3-methoxy-N-methylamphetamine
MMDMA 172518-52-4
3,4-Methylenedioxy-N,N-dimethylamphetamine MDDM, MDDMA 74698-50-3
3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine
MDMOH, MDMHA, MDHMA FLEA 214414-88-7
3,4-Methylenedioxy-N-ethyl-N-hydroxyamphetamine MDEOH, MDEHA, MDHEA TESS, "Nextasy"
3,4-Methylenedioxy-2,5-dimethoxyamphetamine
DMMDA 15183-13-8
4,5-Methylenedioxy-2,3-dimethoxyamphetamine
DMMDA-2 15183-26-3
3,4-Methylenedioxyphentermine
MDPH 39235-63-7
3,4-Methylenedioxy-N-methylphentermine
MDMP 81262-69-3
3,4-Methylenedioxycathinone βk-MDA, MDC 80535-73-5
3,4-Methylenedioxy-N-methylcathinone
βk-MDMA, MDMC Methylone 186028-79-5
3,4-Methylenedioxy-N-ethylcathinone
βk-MDEA, MDEC Ethylone 1112937-64-0
3,4-Methylenedioxy-5-methyl-N-ethylcathinone 5-Me-βk-MDEA 5-Methylethylone 1364933-82-3
1,3-Benzodioxolylbutanamine
BDB J 42542-07-4
N-Methyl-1,3-benzodioxolylbutanamine
MBDB Methyl-J; "Eden" 135795-90-3
N-Ethyl-1,3-benzodioxolylbutanamine
EBDB Ethyl-J 167394-39-0
β-Methoxy-1,3-benzodioxolylbutanamine
BOH 73304-06-0
β-Keto-N-methyl-1,3-benzodioxolylbutanamine
βk-MBDB Butylone 802575-11-7
β-Keto-N-ethyl-1,3-benzodioxolylbutanamine
βk-EBDB Eutylone 802855-66-9
β-Keto-N,N-dimethyl-1,3-benzodioxolylbutanamine
βk-DMBDB Dibutylone 802286-83-5
1,3-Benzodioxolylpentanamine BDP K
N-Methyl-1,3-benzodioxolylpentanamine
MBDP Methyl-K 952016-78-3
N-Ethyl-1,3-benzodioxolylpentanamine
EBDP Ethyl-K 952016-47-6
2-(1,3-Benzodioxol-5-yl)-1-(propan-2-yl)-N-methylethanamine α-iPr-MDMPEA UWA-104
2-(1,3-Benzodioxol-5-yl)-1-cyclopropyl-N-methylethanamine α-cPr-MDMPEA UWA-101 1350821-24-7
2-(1,3-benzodioxol-5-yl)-N-methyl-1-phenylethanamine α-Ph-MDMPEA UWA-001
β-Keto-N-methyl-1,3-benzodioxolylpentanamine
βk-MBDP, βk-Methyl-K Pentylone 698963-77-8
β-Keto-N-ethyl-1,3-benzodioxolylpentanamine βk-EBDP Ephylone 727641-67-0

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 (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-propene
Isosafrole 120-58-1
3,4-Methylenedioxyphenyl-2-propene
Safrole, Shikimol 94-59-7
4,5-Methylenedioxyphenyl-3-methoxy-2-propene
Myristicin 607-91-0
3,4-Methylenedioxyphenyl-1-propanone
MDP1P 28281-49-4
3,4-Methylenedioxyphenyl-2-propanone
MDP2P 4676-39-5
3,4-Methylenedioxybenzaldehyde Piperonal 120-57-0
3,4-Methylenedioxyphenol Sesamol 533-31-3
5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine
Piperine (also chavicine) 94-62-2
3,4-Methylenedioxycinnamylpiperidine Ilepcimide 23434-86-8
trans-4-(4-Fluorophenyl)-3-[(3,4-methylenedioxy)phenoxy]methylpiperidine Paroxetine 61869-08-7
5,6-Methylenedioxy-2-aminoindane
5,6-MDAI, MDAI 132741-81-2
5,6-Methylenedioxy-N-methyl-2-aminoindane
5,6-MDMAI, MDMAI 132741-82-3
6,7-Methylenedioxy-2-aminotetralin
6,7-MDAT 101625-35-8
6,7-Methylenedioxy-2-methylaminotetralin 6,7-MDMAT 34620-52-5
3,4-Methylenedioxy-1-benzylpiperazine
MDBZP Piperonylpiperazine 32231-06-4
3,4-Methylenedioxy-α-pyrrolidinopropiophenone
MDPPP 783241-66-7
3',4'-Methylenedioxy-α-pyrrolidinobutiophenone MDPBP 784985-33-7
3,4-Methylenedioxy-α-pyrrolidinopentiophenone MDPV 687603-66-3
3,4-Methylenedioxy-α-pyrrolidinohexiophenone MDPHP 776994-64-0
Methylenedioxyphenmetrazine MDPM 3,4-Methylenedioxyphenmetrazine[3]
Methyl (1,3-benzodioxol-5-yl)(piperidin-2-yl)acetate MDMPH 3,4-Methylenedioxymethylphenidate
4-Methyl-5-(1,3-benzodioxol-5-yl)-4,5-dihydro-1,3-oxazol-2-amine MDMAR 3',4'-Methylenedioxy-4-methylaminorex 1445573-16-9
1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepine
GYKI-52895 869360-93-0
3,4-Ethylidenedioxyamphetamine EIDA 125299-84-5
3,4-isopropylidenedioxyamphetamine IDA
1-(2,2-Difluoro-1,3-benzodioxol-5-yl)propan-2-amine
DFMDA 910393-51-0
6-(2-aminopropyl)-5-methoxy-1,3-benzoxathiol 4T-MMDA-2 133787-69-6
1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-methylpropan-2-amine EDMA 133787-66-3
1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine 5-APDB 152624-03-8
1-(1,3-dihydro-2-benzofuran-5-yl)-N-methylpropan-2-amine IBF5MAP 201407-56-9
1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine 6-APDB 152623-93-3
1-(1-benzofuran-5-yl)propan-2-amine 5-APB 286834-81-9
N-methyl-1-(1-benzofuran-5-yl)propan-2-amine 5-MAPB 1354631-77-8
N-ethyl-1-(1-benzofuran-5-yl)propan-2-amine 5-EAPB 1445566-01-7
N-methyl-1-(1-benzofuran-5-yl)butan-2-amine 5-MBPB
1-(1-benzofuran-6-yl)propan-2-amine 6-APB 286834-85-3
N-methyl-1-(1-benzofuran-6-yl)propan-2-amine 6-MAPB 1354631-79-0
1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine 5-APDI IAP 13396-94-6
1-(2,3-dihydro-1H-inden-5-yl)-N-methylpropan-2-amine 5-MAPDI IMP 1310153-27-5
1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-2-amine 6-APT TAP 3160-20-1
1-(naphthalen-2-yl)propan-2-amine NAP PAL-287 18085-03-5
N-methyl-1-(naphthalen-2-yl)propan-2-amine MNAP Methamnetamine
1-(1-benzothiophen-5-yl)propan-2-amine 5-APBT 1368128-53-3
1-(1H-indol-5-yl)propan-2-amine 5-API 5-IT 3784-30-3
1-(1H-1,3-benzodiazol-5-yl)propan-2-amine 752145-76-9
1-(1,3-benzoxazol-5-yl)propan-2-amine 1368557-51-0
1-(1,3-benzothiazol-6-yl)propan-2-amine 1896565-11-9
1-(2,1,3-benzoxadiazol-5-yl)propan-2-amine 910413-33-1
1-{imidazo[1,2-a]pyridin-6-yl}propan-2-amine 1337128-11-6
1-(1,2,3-benzothiadiazol-5-yl)propan-2-amine 1380044-39-2
1-(quinoxalin-6-yl)propan-2-amine 910407-54-4

See also

References

External links