Substituted methylenedioxyphenethylamine

Methylenedioxyphenethylamine (MDPEA)

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 notable MDxx class substances 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 Ref
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 1391487-26-5 [2]
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

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. In addition to the (i) and (ii) compounds, MDxx compounds are closely related to the other two main phenylethylamine classes, those being substituted amphetamines and substituted cathinones. Like amphetamines and cathinones, MDxx compounds derive most if not all of their stimulant effects from the phenylethylamine core, in fact most MDxx compounds can also be grouped with cathinones and or amphetamines due to having similar functional groups, but in most cases any compound with a methylenedioxy group attached will be grouped as an MDxx compound due to the unique hallucinogenic and empathogenic/entactogenic effects that are not present in most other amphetamines and present to a lesser extent in most cathinones.

Structure Chemical Name Abbreviations Other Names CAS number Ref
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 "Monkey Dust" 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 (PAL-1046) 1178720-66-5
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
1-(1,3-Benzodiazol-5-yl)-N-methylpropan-2-amine
1-(2,1,3-Benzoxadiazol-5-yl)-N-methylpropan-2-amine ODMA 2567501-96-4
1-(2,1,3-Benzothiadiazol-5-yl)-N-methylpropan-2-amine TDMA 2302389-87-1
1-(2,1,3-Benzoselenadiazol-5-yl)-N-methylpropan-2-amine SeDMA
1-(Benzo[d][1,3]oxathiol-5-yl)-N-methylpropan-2-amine MY100 [4][5]
1-(Benzo[d][1,3]oxathiol-5-yl)-N,N-dimethylpropan-2-amine MY101 [4][6]
1-(Benzo[d][1,3]oxathiol-6-yl)-N-methylpropan-2-amine MY200 [4][7]
1-(Benzo[b]thiophen-6-yl)-N-methylpropan-2-amine MY300 [4][8]
1-(Benzo[b]thiophen-5-yl)-N-methylpropan-2-amine 5-MAPBT MY400 2613382-32-2 [4][9]
1-(Benzo[d]thiazol-5-yl)-N-methylpropan-2-amine 5-BZT-MDMA MYCO-006? [10][11][12][13]
1-(Benzo[d]thiazol-6-yl)-N-methylpropan-2-amine 6-BZT-MDMA MYCO-007? [10][14][12][13]
? MYCO-002 [15][16][17]

See also

References

  1. ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: From Structure to Function. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  2. ^ Dr. Matthias Grill, Novel Safrylamine derivates having prodrug properties. Patent WO 2022/053696
  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.
  4. ^ a b c d e Mydecine (5 January 2024). "Novel short-acting psychoactive compounds of the mdma class". Google Patents. Retrieved 23 October 2024.
  5. ^ "1-(1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
  6. ^ "1-(1,3-benzoxathiol-5-yl)-N,N-dimethylpropan-2-amine". PubChem. Retrieved 23 October 2024.
  7. ^ "1-(1,3-benzoxathiol-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
  8. ^ "1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
  9. ^ "[1-(1-Benzothiophen-5-yl)propan-2-yl](methyl)amine". PubChem. Retrieved 23 October 2024.
  10. ^ a b Mydecine (13 June 2023). "Short-acting 3,4-methylenedioxymethamphetamine (mdma) analogs incorporating benzothiazole". Google Patents. Retrieved 23 October 2024.
  11. ^ "1-(1,3-benzothiazol-5-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
  12. ^ a b "2309151616480990.pdf" (PDF). Retrieved 23 October 2024. MYCO - 006 and 007 represent families of molecules that are based on MDMA molecules. MYCO -006 and MYCO – 007 have been developed in order to reduce the overall acute experience time of Generation 1 MDMA by increasing the metabolism properties of the drug.
  13. ^ a b Mydecine Innovations Group (19 July 2022). "Mydecine Files Full Patent Application Covering MYCO-006 Family of Novel Short-Acting MDMA Analogs". GlobeNewswire News Room. Retrieved 23 October 2024. Mydecine [...] announced it has successfully synthesized multiple short-acting MDMA analogs. This family of analogs have been specifically designed by experts at Mydecine to have a shorter half life than traditional MDMA. The Company has named this family of novel molecules MYCO-006 and have applied for patent coverage with the World Intellectual Property Organization.
  14. ^ "1-(1,3-benzothiazol-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
  15. ^ "MYCO 002". AdisInsight. 28 November 2021. Retrieved 23 October 2024.
  16. ^ "Delving into the Latest Updates on MYCO-002 with Synapse". Synapse. 19 September 2024. Retrieved 23 October 2024.
  17. ^ Mydecine Innovations Group (7 April 2021). "Mydecine Announces Four Lead Novel Drug Candidates and Prepares for Pre-IND Meetings with the FDA and Health Canada To Prepare For Human Clinical". GlobeNewswire News Room. Retrieved 23 October 2024. MYCO - 002 is an entactogenic compound that has been created with the goal of reducing harm and improving the safety profile vs. traditional MDMA.

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