Substituted methylenedioxyphenethylamine

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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]

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[edit]

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

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

Related compounds[edit]

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
Isosafrole acsv.svg 3,4-Methylenedioxyphenyl-1-propene Isosafrole 120-58-1
Safrole-Line-Structure.png 3,4-Methylenedioxyphenyl-2-propene Safrole, Shikimol 94-59-7
Myristicin.svg 4,5-Methylenedioxyphenyl-3-methoxy-2-propene Myristicin 607-91-0
Methylenedioxypropiophenone.svg 3,4-Methylenedioxyphenyl-1-propanone MDP1P 28281-49-4
MDP2P.svg 3,4-Methylenedioxyphenyl-2-propanone MDP2P 4676-39-5
Piperonal structure.png 3,4-Methylenedioxybenzaldehyde Piperonal 120-57-0
Sesamol.png 3,4-Methylenedioxyphenol Sesamol 533-31-3
Piperin.svg 5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine Piperine (also chavicine) 94-62-2
Ilepcimide.png 3,4-Methylenedioxycinnamylpiperidine Ilepcimide 23434-86-8
Paroxetine-2D-skeletal.svg trans-4-(4-Fluorophenyl)-3-[(3,4-methylenedioxy)phenoxy]methylpiperidine Paroxetine 61869-08-7
MDAI.svg 5,6-Methylenedioxy-2-aminoindane 5,6-MDAI, MDAI 132741-81-2
MDMAI.svg 5,6-Methylenedioxy-N-methyl-2-aminoindane 5,6-MDMAI, MDMAI 132741-82-3
6,7-Methylenedioxy-2-aminotetralin2.png 6,7-Methylenedioxy-2-aminotetralin 6,7-MDAT 101625-35-8
MDMAT-structure.png 6,7-Methylenedioxy-2-methylaminotetralin 6,7-MDMAT 34620-52-5
MDBZP.svg 3,4-Methylenedioxy-1-benzylpiperazine MDBZP Piperonylpiperazine 32231-06-4
MDPPP.svg 3,4-Methylenedioxy-α-pyrrolidinopropiophenone MDPPP 783241-66-7
3',4'-Methylenedioxy-α-pyrrolidinobutiophenone.svg 3',4'-Methylenedioxy-α-pyrrolidinobutiophenone MDPBP 784985-33-7
MDPV.svg 3,4-Methylenedioxy-α-pyrrolidinopentiophenone MDPV 687603-66-3
MDPHP.svg 3,4-Methylenedioxy-α-pyrrolidinohexiophenone MDPHP 776994-64-0
MDPHMZ structure.png 3-methyl-2-(3,4-methylenedioxyphenyl)morpholine MDPM 3,4-Methylenedioxyphenmetrazine[2]
Methylenedioxymethylphenidate structure.png Methyl (1,3-benzodioxol-5-yl)(piperidin-2-yl)acetate MDMPH 3,4-Methylenedioxymethylphenidate
MD4MAR structure.png 4-Methyl-5-(1,3-benzodioxol-5-yl)-4,5-dihydro-1,3-oxazol-2-amine MD-4-MAR 3',4'-Methylenedioxy-4-methylaminorex 1445573-16-9
GYKI 52895.svg 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-2,3-benzodiazepine GYKI-52895 869360-93-0
EDA.svg 3,4-Ethylidenedioxyamphetamine EIDA 125299-84-5
IDA.svg 3,4-isopropylidenedioxyamphetamine IDA
DFMDA.svg 1-(2,2-Difluoro-1,3-benzodioxol-5-yl)propan-2-amine DFMDA 910393-51-0
4T-MMDA-2 structure.png 6-(2-aminopropyl)-5-methoxy-1,3-benzoxathiol 4T-MMDA-2 133787-69-6
EDMA.png 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-methylpropan-2-amine EDMA 133787-66-3
3-desoxy-MDA.svg 1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine 5-APDB 152624-03-8
IBF5MAP structure.png 1-(1,3-dihydro-2-benzofuran-5-yl)-N-methylpropan-2-amine IBF5MAP 201407-56-9
4-desoxy-MDA.svg 1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine 6-APDB 152623-93-3
5-APB.svg 1-(1-benzofuran-5-yl)propan-2-amine 5-APB 286834-81-9
5-MAPB.svg N-methyl-1-(1-benzofuran-5-yl)propan-2-amine 5-MAPB 1354631-77-8
1-(benzofuran-5-yl)-N-ethylpropan-2-amine.png N-ethyl-1-(1-benzofuran-5-yl)propan-2-amine 5-EAPB 1445566-01-7
5-MBPB structure.png N-methyl-1-(1-benzofuran-5-yl)butan-2-amine 5-MBPB
6-APB.svg 1-(1-benzofuran-6-yl)propan-2-amine 6-APB 286834-85-3
6-MAPB structure.png N-methyl-1-(1-benzofuran-6-yl)propan-2-amine 6-MAPB 1354631-79-0
Indanylaminopropane.svg 1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine 5-APDI IAP 13396-94-6
5-MAPDI structure.png 1-(2,3-dihydro-1H-inden-5-yl)-N-methylpropan-2-amine 5-MAPDI IMP 1310153-27-5
Tetralinylaminopropane.svg 1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-2-amine 6-APT TAP 3160-20-1
Naphthylisopropylamine.svg 1-(naphthalen-2-yl)propan-2-amine NAP PAL-287 18085-03-5
Methamnetamine structure.png N-methyl-1-(naphthalen-2-yl)propan-2-amine MNAP Methamnetamine
5-APBTP structure.png 1-(1-benzothiophen-5-yl)propan-2-amine 5-APBT 1368128-53-3
5-IT structure.png 1-(1H-indol-5-yl)propan-2-amine 5-API 5-IT 3784-30-3
5-APBDZ structure.png 1-(1H-1,3-benzodiazol-5-yl)propan-2-amine 752145-76-9
5-APBOX structure.png 1-(1,3-benzoxazol-5-yl)propan-2-amine 1368557-51-0
6-APBTZ structure.png 1-(1,3-benzothiazol-6-yl)propan-2-amine 1896565-11-9
5-APBXDZ structure.png 1-(2,1,3-benzoxadiazol-5-yl)propan-2-amine 910413-33-1
6-APIPY structure.png 1-{imidazo[1,2-a]pyridin-6-yl}propan-2-amine 1337128-11-6
5-APBTDZ structure.png 1-(1,2,3-benzothiadiazol-5-yl)propan-2-amine 1380044-39-2
6-APQOX structure.png 1-(quinoxalin-6-yl)propan-2-amine 910407-54-4

See also[edit]

References[edit]

  1. ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  2. ^ 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.

External links[edit]