Chemistry:4-Chloromethcathinone
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.[1][2]
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.[3]
Neurotoxicity
Its chemical structure closely resembles para-chloromethamphetamine, raising concerns about its potential to readily induce cell death of serotonergic 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.[4]
Pharmacology
Pharmacodynamics
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 to mephedrone[3]
| Drug | Release at DAT
EC50 (nM) |
Release at NET
EC50 (nM) |
Release at SERT
EC50 (nM) |
|---|---|---|---|
| Mephedrone (4-MMC) | 103 ± 16 | 83 ± 20 | 188 ± 22 |
| 4-CMC | 91 ± 11 | 99 ± 18 | 169 ± 20 |
| Drug | Uptake Inhibition at DAT
IC50 (nM) |
Uptake Inhibition at NET
IC50 (nM) |
Uptake Inhibition at SERT
IC50 (nM) |
|---|---|---|---|
| Mephedrone (4-MMC) | 769 ± 106 | 319 ± 40 | 600 ± 99 |
| 4-CMC | 1014 ± 78 | 559 ± 57 | 542 ± 38 |
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.[5]
As of October 2015, 4-CMC is a controlled substance in China.[6]
4-CMC is considered a Schedule 1 substance in Virginia.[7]
In December 2019, the UNODC announced scheduling recommendations placing 4-CMC into Schedule II.[8]
See also
- 3-Chloromethcathinone
- 3-Methylmethcathinone
- 4-Bromomethcathinone
- 4-Chloroamphetamine
- 4-Cl-3-MMC
- 4Cl-PVP
- 4-Ethylmethcathinone
- 4-Methylmethcathinone
- Substituted cathinone
References
- ↑ "Analysis and characterization of the novel psychoactive drug 4-chloromethcathinone (clephedrone)". Forensic Science International 244: e56–e59. November 2014. doi:10.1016/j.forsciint.2014.09.007. PMID 25280452.
- ↑ "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". Forensic Science International 265: 121–124. August 2016. doi:10.1016/j.forsciint.2016.01.018. PMID 26890319.
- ↑ 3.0 3.1 3.2 3.3 "Neurochemical and Cardiovascular Effects of 4-Chloro Ring-Substituted Synthetic Cathinones in Rats". The Journal of Pharmacology and Experimental Therapeutics 385 (3): 162–170. June 2023. doi:10.1124/jpet.122.001478. PMID 36669877.
- ↑ "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". Neurotoxicity Research 38 (2): 536–551. August 2020. doi:10.1007/s12640-020-00227-8. PMID 32506339.
- ↑ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 1 June 2015. http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/juni/23-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara.
- ↑ "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. http://www.sfda.gov.cn/WS01/CL0056/130753.html.
- ↑ "18VAC110-20-322. Placement of Chemicals in Schedule I." (in English). Commonwealth of Virginia. 2 December 2015. http://law.lis.virginia.gov/admincode/title18/agency110/chapter20/section322/.
- ↑ "World Health Organization recommends 12 NPS for scheduling". WHO. December 2019. https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3.
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