4-Chloromethcathinone
{{Short description|Simulant drug of the cathinone class}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = 1-(4-chlorophenyl)-2-(methylamino)-1-propanone
| image = 4-Chloromethcathinone.svg
| tradename =
| pregnancy_category =
| legal_BR = F2
| legal_DE = Anlage I
| legal_UK = Class B
| legal_UN = P II
| legal_status = Illegal in China and Sweden
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref =
| CAS_number = 1225843-86-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PTAYYYZMMT
| ATC_prefix =
| ATC_suffix =
| PubChem = 82100418
| KEGG = C22721
| ChemSpiderID_Ref =
| ChemSpiderID = 25630416
| DTXSID = DTXSID201014163
| C = 10
| H = 12
| Cl = 1
| N = 1
| O = 1
| melting_point = 198
| smiles = ClC1=CC=C(C(C(C)NC)=O)C=C1
| StdInChI_Ref =
| StdInChI = 1S/C10H12ClNO/c1-7(12-2)10(13)8-3-5-9(11)6-4-8/h3-7,12H,1-2H3
| StdInChIKey_Ref =
| StdInChIKey = UEJBEYOXRNGPEI-UHFFFAOYSA-N
}}
4-Chloromethcathinone (also known as 4-CMC and clephedrone) is a stimulant drug of the cathinone class that has been sold online as a designer drug.{{cite journal | vauthors = Taschwer M, Weiß JA, Kunert O, Schmid MG | title = Analysis and characterization of the novel psychoactive drug 4-chloromethcathinone (clephedrone) | journal = Forensic Science International | volume = 244 | pages = e56–e59 | date = November 2014 | pmid = 25280452 | doi = 10.1016/j.forsciint.2014.09.007 }}{{cite journal | vauthors = Klavž J, Gorenjak M, Marinšek M | title = Suicide attempt with a mix of synthetic cannabinoids and synthetic cathinones: Case report of non-fatal intoxication with AB-CHMINACA, AB-FUBINACA, alpha-PHP, alpha-PVP and 4-CMC | journal = Forensic Science International | volume = 265 | pages = 121–124 | date = August 2016 | pmid = 26890319 | doi = 10.1016/j.forsciint.2016.01.018 }}
4-CMC produces similar effects to mephedrone, and has been sold as an alternative in countries where mephedrone was scheduled.
Adverse effects
= Short-term =
4-CMC produces similar side effects to mephedrone, including: increased blood pressure, tachycardia, hyperthermia, and anxiety.{{cite journal | vauthors = Chojnacki MR, Thorndike EB, Partilla JS, Rice KC, Schindler CW, Baumann MH | title = Neurochemical and Cardiovascular Effects of 4-Chloro Ring-Substituted Synthetic Cathinones in Rats | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 385 | issue = 3 | pages = 162–170 | date = June 2023 | pmid = 36669877 | pmc = 10201577 | doi = 10.1124/jpet.122.001478 }}
= Neurotoxicity =
Its chemical structure closely resembles para-chloromethamphetamine, raising concerns about its potential to readily induce cell death of serotoninergic neurons. However, no neurotoxicity of this kind has been found to occur, but studies involving mice do indicate that it is neurotoxic through other mechanisms, similarly to other cathinones. 4-CMC is cytotoxic and induces oxidative stress, more so than 4-MMC.{{cite journal |vauthors=Wojcieszak J, Kuczyńska K, Zawilska JB |date=August 2020 |title=Four Synthetic Cathinones: 3-Chloromethcathinone, 4-Chloromethcathinone, 4-Fluoro-α-Pyrrolidinopentiophenone, and 4-Methoxy-α-Pyrrolidinopentiophenone Produce Changes in the Spontaneous Locomotor Activity and Motor Performance in Mice with Varied Profiles |journal=Neurotoxicity Research |volume=38 |issue=2 |pages=536–551 |doi=10.1007/s12640-020-00227-8 |pmc=7334283 |pmid=32506339}}
Pharmacology
= Pharmacodynamics =
Similar to mephedrone, 4-CMC mainly acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), and partially as a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI) with similar potency.
Legality
4-CMC is an Anlage I controlled drug in Germany.
Sweden's public health agency suggested classifying 4-Chloromethcathinone (klefedron) as illegal narcotic on June 1, 2015.{{cite web |url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/juni/23-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara |title=23 nya ämnen kan klassas som narkotika eller hälsofarlig vara | trans-title = 23 new substances can be classified as narcotic drugs or substances dangerous to health | work = Folkhälsomyndigheten | trans-work = The Public Health Authority |date=1 June 2015 |access-date=5 September 2015 |language=Swedish}}
As of October 2015, 4-CMC is a controlled substance in China.{{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 | trans-title = Notice on Issuing the Measures for the Listing and Control of Non-Medicinal Narcotic Drugs and Psychotropic Substances | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | 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 }}
4-CMC is considered a Schedule 1 substance in Virginia.{{cite web | url=http://law.lis.virginia.gov/admincode/title18/agency110/chapter20/section322/ | title=18VAC110-20-322. Placement of Chemicals in Schedule I. | publisher=Commonwealth of Virginia | date=2 December 2015 | language=English | access-date= 11 March 2016}}
In December 2019, the UNODC announced scheduling recommendations placing 4-CMC into Schedule II.{{cite web |url= https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3 |date = December 2019 | work = WHO | title = World Health Organization recommends 12 NPS for scheduling }}
See also
References
{{reflist}}
{{Stimulants}}
{{Phenethylamines}}
{{DEFAULTSORT:Chloromethcathinone, 4-}}