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3,4-Dimethylmethcathinone: Difference between revisions

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{{Short description|Designer stimulant drug}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| IUPAC_name = (±)-1-(3,4-dimethylphenyl)-2-(methylamino)propan-1-one
| 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 =
| 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


<!--Pharmacokinetic data--> <!--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
| ChemSpiderID = 25630192
| 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
| 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 = IBZRXTVDTGVBIS-UHFFFAOYSA-N


==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 compound
3,4-Dimethylmethcathinone
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • (±)-1-(3,4-Dimethylphenyl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H17NO
Molar mass191.274 g·mol
3D model (JSmol)
SMILES
  • Cc1ccc(C(=O)C(C)NC)cc1C
InChI
  • InChI=1S/C12H17NO/c1-8-5-6-11(7-9(8)2)12(14)10(3)13-4/h5-7,10,13H,1-4H3
  • Key:IBZRXTVDTGVBIS-UHFFFAOYSA-N
  (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

References

  1. "EMCDDA Annual Report 2010" (PDF). Archived from the original (PDF) on 2012-03-14. Retrieved 2011-10-03.
  2. 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.
  3. 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.
  4. "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.
  5. "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.
  6. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). U.S. Department of Justice. February 2023. Retrieved 2023-03-05.
Stimulants
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
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Cholinergics
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Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
ATC code: N06B
Phenethylamines
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous
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