Substituted methylenedioxyphenethylamine
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
- 2Cs, DOx, 25-NB
- Substituted amphetamines
- Substituted benzofurans
- Substituted cathinones
- Substituted phenethylamines
- Substituted phenmetrazines
- Substituted tryptamines