Substituted methylenedioxyphenethylamine
(Redirected from Substituted methylenedioxy- phenethylamine)
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
[edit]The compounds most commonly regarded as comprising the family of MDxx derivatives include:
.svg)
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 | 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 | 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-ethylpropan-2-amine.png){kind=small} |
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
[edit]- 2Cs, DOx, 25-NB
- Substituted amphetamines
- Substituted benzofurans
- Substituted cathinones
- Substituted phenethylamines
- Substituted phenmetrazines
- Substituted tryptamines
References
[edit]- ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: From Structure to Function. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
- ^ Dr. Matthias Grill, Novel Safrylamine derivates having prodrug properties. Patent WO 2022/053696
- ^ 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.
- ^ a b c d e Mydecine (5 January 2024). "Novel short-acting psychoactive compounds of the mdma class". Google Patents. Retrieved 23 October 2024.
- ^ "1-(1,3-benzoxathiol-5-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
- ^ "1-(1,3-benzoxathiol-5-yl)-N,N-dimethylpropan-2-amine". PubChem. Retrieved 23 October 2024.
- ^ "1-(1,3-benzoxathiol-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
- ^ "1-(1-benzothiophen-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
- ^ "[1-(1-Benzothiophen-5-yl)propan-2-yl](methyl)amine". PubChem. Retrieved 23 October 2024.
- ^ a b Mydecine (13 June 2023). "Short-acting 3,4-methylenedioxymethamphetamine (mdma) analogs incorporating benzothiazole". Google Patents. Retrieved 23 October 2024.
- ^ "1-(1,3-benzothiazol-5-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
- ^ 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.
- ^ 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.
- ^ "1-(1,3-benzothiazol-6-yl)-N-methylpropan-2-amine". PubChem. Retrieved 23 October 2024.
- ^ "MYCO 002". AdisInsight. 28 November 2021. Retrieved 23 October 2024.
- ^ "Delving into the Latest Updates on MYCO-002 with Synapse". Synapse. 19 September 2024. Retrieved 23 October 2024.
- ^ 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.