Substituted methylenedioxyphenethylamine explained

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]

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:

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

StructureChemical NameAbbreviationsOther NamesCAS number
Isosafrole 120-58-1
Safrole, Shikimol 94-59-7
Myristicin 607-91-0
MDP1P 28281-49-4
MDP2P 4676-39-5
Piperonal 120-57-0
Sesamol 533-31-3
Piperine (also chavicine) 94-62-2
Ilepcimide 23434-86-8
Paroxetine 61869-08-7
5,6-MDAI, MDAI 132741-81-2
5,6-MDMAI, MDMAI 132741-82-3
6,7-MDAT 101625-35-8
6,7-MDMAT 34620-52-5
MDBZP Piperonylpiperazine 32231-06-4
MDPPP 783241-66-7
MDPBP 784985-33-7
MDPV 687603-66-3
MDPHP 776994-64-0
MDPM 3,4-Methylenedioxyphenmetrazine[3]
Methyl (1,3-benzodioxol-5-yl)(piperidin-2-yl)acetate MDMPH 3,4-Methylenedioxymethylphenidate
MDMAR 3',4'-Methylenedioxy-4-methylaminorex 1445573-16-9
GYKI-52895 869360-93-0
EIDA 125299-84-5
3,4-isopropylidenedioxyamphetamine IDA
DFMDA 910393-51-0
6-(2-aminopropyl)-5-methoxy-1,3-benzoxathiol 4T-MMDA-2 133787-69-6
EDMA 133787-66-3
5-APDB 152624-03-8
IBF5MAP 201407-56-9
6-APDB 152623-93-3
5-APB 286834-81-9
5-MAPB 1354631-77-8
5-EAPB 1445566-01-7
5-MBPB
6-APB 286834-85-3
6-MAPB 1354631-79-0
5-APDI IAP 13396-94-6
5-MAPDI IMP 1310153-27-5
6-APT TAP 3160-20-1
NAP PAL-287 18085-03-5
MNAP Methamnetamine
1-(1-benzothiophen-5-yl)propan-2-amine 5-APBT 1368128-53-3
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-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

External links

Notes and References

  1. Book: Daniel . Trachsel . David . Lehmann . Christoph . Enzensperger . vanc . Phenethylamine: From Structure to Function . Nachtschatten Verlag AG . 2013 . 978-3-03788-700-4.
  2. https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022053696&_cid=P20-L10J3Y-27843-1 Dr. Matthias Grill, Novel Safrylamine derivates having prodrug properties. Patent WO 2022/053696
  3. Świst M, Wilamowski J, Zuba D, Kochana J, Parczewski A . 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 . May 2005 . 15749360 . 10.1016/j.forsciint.2004.06.016 .