Revision as of 06:04, 4 October 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKey← Previous edit | Latest revision as of 02:16, 12 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix | ||
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{{Short description|Designer stimulant drug}} | |||
{{Drugbox | {{Drugbox | ||
| Verifiedfields = changed | |||
⚫ | | IUPAC_name = (±)-1-(3,4- |
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| verifiedrevid = 453845081 | |||
| image = 34DMMC_structure.png | |||
⚫ | | IUPAC_name = (±)-1-(3,4-Dimethylphenyl)-2-(methylamino)propan-1-one | ||
| image = 3,4-DMMC.svg | |||
| image_class = skin-invert-image | |||
<!--Clinical data--> | <!--Clinical data-->| tradename = | ||
| |
| pregnancy_category = | ||
| legal_UK = Class B | |||
| pregnancy_category = | |||
| legal_US = Schedule I | |||
| legal_status = | |||
| legal_DE = Anlage II | |||
| routes_of_administration = | | routes_of_administration = <!--Pharmacokinetic data--> | ||
⚫ | | bioavailability = | ||
⚫ | | protein_bound = | ||
⚫ | | metabolism = | ||
⚫ | | elimination_half-life = | ||
⚫ | | excretion = <!--Identifiers--> | ||
| CAS_number_Ref = {{cascite|changed|CAS}} | |||
⚫ | | CAS_number = 1082110-00-6 | ||
| UNII_Ref = {{fdacite|changed|FDA}} | |||
| UNII = C4EW58DTW5 | |||
⚫ | | ATC_prefix = none | ||
⚫ | | ATC_suffix = | ||
⚫ | | PubChem = 52988261 | ||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
⚫ | | ChemSpiderID = 25630192 | ||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
⚫ | | StdInChI = 1S/C12H17NO/c1-8-5-6-11(7-9(8)2)12(14)10(3)13-4/h5-7,10,13H,1-4H3 | ||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | |||
⚫ | | StdInChIKey = IBZRXTVDTGVBIS-UHFFFAOYSA-N | ||
<!-- |
<!--Chemical data-->| C = 12 | ||
| H = 17 | |||
⚫ | | bioavailability |
||
| N = 1 | |||
⚫ | | protein_bound |
||
| O = 1 | |||
⚫ | | metabolism |
||
⚫ | | smiles = Cc1ccc(C(=O)C(C)NC)cc1C | ||
⚫ | | elimination_half-life = |
||
⚫ | }} | ||
| excretion = | |||
'''3,4-Dimethylmethcathinone''' ('''3,4-DMMC''') is a ] drug first reported in 2010 as a ] analogue of ], apparently produced in response to the banning of mephedrone, following its widespread abuse in many countries in Europe and around the world.<ref>{{Cite web |url=http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf |title=EMCDDA Annual Report 2010 |access-date=2011-10-03 |archive-date=2012-03-14 |archive-url=https://web.archive.org/web/20120314043454/http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf |url-status=dead }}</ref> 3,4-DMMC has been seized as a designer drug in ].<ref>{{cite journal | vauthors = Locos O, Reynolds D | title = The characterization of 3,4-dimethylmethcathinone (3,4-DMMC) | journal = Journal of Forensic Sciences | volume = 57 | issue = 5 | pages = 1303–6 | date = September 2012 | pmid = 22564211 | doi = 10.1111/j.1556-4029.2012.02142.x | s2cid = 205770717 }}</ref> ''In vitro'', 3,4-DMMC was shown to be a ] substrate that potently inhibits norepinephrine and serotonin reuptake, and to a lesser extent dopamine reuptake.<ref name="pmid28755886">{{cite journal |vauthors=Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME | title = Pharmacological profile of mephedrone analogs and related new psychoactive substances | journal = Neuropharmacology | volume = 15 | issue = 134 | pages = 4–12 | year = 2018 | pmid = 28755886 | doi=10.1016/j.neuropharm.2017.07.026| s2cid = 28786127 | url = https://edoc.unibas.ch/57357/1/20170920120908_59c23e44b5f0e.pdf }}</ref> | |||
⚫ | <!--Identifiers--> | ||
⚫ | | CAS_number = | ||
⚫ | | ATC_prefix = none | ||
⚫ | | ATC_suffix |
||
⚫ | | PubChem = 52988261 |
||
⚫ | | |
||
| InChI = 1/C12H17NO/c1-8-5-6-11(7-9(8)2)12(14)10(3)13-4/h5-7,10,13H,1-4H3 | |||
| InChIKey = IBZRXTVDTGVBIS-UHFFFAOYAD | |||
⚫ | | |
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⚫ | | |
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==Legal Status== | |||
<!--Chemical data--> | |||
| C=12 | H=17 | N=1 | O=1 | |||
| molecular_weight = 191.269 g/mol | |||
⚫ | | smiles = Cc1ccc(C(=O)C(C)NC)cc1C | ||
⚫ | }} | ||
As of October 2015 3,4-DMMC is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref> | |||
'''3,4-Dimethylmethcathinone''' ('''3,4-DMMC''') is a ] drug first reported in 2010 as a ] analogue of ], apparently produced in response to the banning of mephedrone, following its widespread abuse in many countries in Europe and around the world.<ref></ref> | |||
3,4-DMMC is banned in the Czech Republic.<ref>{{cite web | url=http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | title=Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.) | publisher=Ministerstvo zdravotnictví | language=cs | access-date=2016-02-06 | archive-date=2016-03-09 | archive-url=https://web.archive.org/web/20160309174659/http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | url-status=dead }}</ref> | |||
⚫ | ==See also== | ||
In the United States 3,4-DMMC is considered a ] controlled substance as a positional isomer of ] (4-MEC).<ref>{{cite web |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf |title=Lists of: Scheduling Actions Controlled Substances Regulated Chemicals|publisher=U.S. Department of Justice|date=February 2023 | |||
|access-date=2023-03-05}}</ref> | |||
⚫ | == See also == | ||
* ] | |||
* ] | |||
* ] | * ] | ||
* ] | * ] | ||
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== References == | == References == | ||
{{Reflist}} | {{Reflist}} | ||
{{Stimulants}} | {{Stimulants}} | ||
{{Phenethylamines}} | |||
{{DEFAULTSORT:Dimethylmethcathinone, 3,4-}} | |||
] | ] | ||
] | |||
] | |||
{{nervous-system-drug-stub}} |
Latest revision as of 02:16, 12 January 2025
Designer stimulant drug Pharmaceutical compoundClinical data | |
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Chemical and physical data | |
Formula | C12H17NO |
Molar mass | 191.274 g·mol |
3D model (JSmol) | |
SMILES
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InChI
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(what is this?) (verify) |
3,4-Dimethylmethcathinone (3,4-DMMC) is a stimulant drug first reported in 2010 as a designer drug analogue of mephedrone, apparently produced in response to the banning of mephedrone, following its widespread abuse in many countries in Europe and around the world. 3,4-DMMC has been seized as a designer drug in Australia. In vitro, 3,4-DMMC was shown to be a monoamine transporter substrate that potently inhibits norepinephrine and serotonin reuptake, and to a lesser extent dopamine reuptake.
Legal Status
As of October 2015 3,4-DMMC is a controlled substance in China.
3,4-DMMC is banned in the Czech Republic.
In the United States 3,4-DMMC is considered a Schedule I controlled substance as a positional isomer of 4-Methylethcathinone (4-MEC).
See also
- Serotonin–norepinephrine–dopamine reuptake inhibitor
- Serotonin–norepinephrine reuptake inhibitor
- Substituted cathinone
- Indanylaminopropane
- Methylone
- Xylopropamine
References
- "EMCDDA Annual Report 2010" (PDF). Archived from the original (PDF) on 2012-03-14. Retrieved 2011-10-03.
- Locos O, Reynolds D (September 2012). "The characterization of 3,4-dimethylmethcathinone (3,4-DMMC)". Journal of Forensic Sciences. 57 (5): 1303–6. doi:10.1111/j.1556-4029.2012.02142.x. PMID 22564211. S2CID 205770717.
- Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME (2018). "Pharmacological profile of mephedrone analogs and related new psychoactive substances" (PDF). Neuropharmacology. 15 (134): 4–12. doi:10.1016/j.neuropharm.2017.07.026. PMID 28755886. S2CID 28786127.
- "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
- "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví. Archived from the original (PDF) on 2016-03-09. Retrieved 2016-02-06.
- "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). U.S. Department of Justice. February 2023. Retrieved 2023-03-05.