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ECHA InfoCard | 100.257.446 |
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Formula | C10H12ClNO |
Molar mass | 197.66 g·mol−1 |
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Melting point | 198 °C (388 °F) |
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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.
4-CMC produces similar side effects to mephedrone, including: increased blood pressure, tachycardia, hyperthermia, and anxiety. [3]
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, but studies involving mice do indicate that it is neurotoxic through other mechanisms. 4-CMC is cytotoxic and induces oxidative stress. [4]
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. [3]
Drug | Release at DAT EC50 (nM) | Release at NET EC50 (nM) | Release at SERT EC50 (nM) |
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Mephedrone | 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 | 769 ± 106 | 319 ± 40 | 600 ± 99 |
4-CMC | 1014 ± 78 | 559 ± 57 | 542 ± 38 |
Clephedrone 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]
Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families. It is the β-keto analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.
Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.
Methedrone is a recreational drug of the cathinone chemical class. Chemically, methedrone is closely related to para-methoxymethamphetamine (PMMA), methylone and mephedrone. Methedrone received media attention in 2009 after the death of two young Swedish men. In both cases toxicology analysis showed methedrone was the only drug present in both men during the time of their overdose and subsequent deaths.
Mephedrone, also known as 4-methylmethcathinone, 4-MMC, and 4-methylephedrone, is a synthetic stimulant drug belonging to the amphetamine and cathinone classes. It is commonly referred to by slang names such as drone, M-CAT, White Magic, meow meow, and bubble. Chemically, it is similar to the cathinone compounds found in the Khat plant, native to eastern Africa.
Ethcathinone, also known as ethylpropion or ETH-CAT, is a stimulant drug of the phenethylamine, amphetamine, and cathinone chemical classes. It is an active metabolite of the prodrug diethylcathinone and is fully responsible for its effects. Ethcathinone has been identified as an ingredient in both quasi-legal "party pills", and, along with mephedrone, has also been reported as having been sold as "ecstasy" in the Australian city of Cairns.
4-Bromomethcathinone is a psychoactive drug and research chemical of the phenethylamine, amphetamine, and cathinone chemical classes. It acts as a serotonin and norepinephrine reuptake inhibitor, but acts more like an antidepressant than a stimulant. Halogenated cathinones, including 4-BMC, possess neurotoxic and cytotoxic properties.
MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.
α-Pyrrolidinopentiophenone (α-PVP), also known as α-pyrrolidinovalerophenone, O-2387, β-keto-prolintane, prolintanone, or desmethylpyrovalerone, is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug and often consumed for recreational reasons. α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.
Naphyrone, also known as O-2482 and naphthylpyrovalerone, is a substituted cathinone drug derived from pyrovalerone that acts as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), producing stimulant effects and has been reported as a novel designer drug. No safety or toxicity data is available on the drug.
α-Pyrrolidinobutiophenone (α-PBP) is a stimulant compound developed in the 1960s which has been reported as a novel designer drug. It can be thought of as the homologue lying between the two better known drugs α-PPP and α-PVP.
Pentylone is a stimulant developed in the 1960s. It is a substituted cathinone that has been identified in some samples of powders sold as "NRG-1", along with varying blends of other cathinone derivatives including flephedrone, MDPBP, MDPV, and 4-MePPP. It was also found in combination with 4-MePPP being sold as "NRG-3". Reports indicate side effects include paranoia, agitation, and insomnia, with effects lasting for several days at high doses.
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.
Pentedrone is a stimulant of the cathinone class that has been sold as a designer drug and has been found since 2010 as an ingredient in a number of "bath salt" mixes sold as legal highs.
3-Methylmethcathinone (3-MMC), also known as metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is a monoamine transporter substrate that potently releases and inhibits the reuptake of dopamine and norepinephrine, as well as displaying moderate serotonin releasing activity.
4'-Methoxy-α-pyrrolidinopentiophenone is a stimulant drug of the cathinone class that has been sold online as a designer drug.
3',4'-Dimethoxy-α-pyrrolidinopentiophenone is a synthetic stimulant drug of the cathinone class that has been sold online as a designer drug. It is a relatively weak inhibitor of serotonin reuptake and has little affinity in vitro for dopamine or noradrenaline transporters.
N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.
3-Chloromethcathinone (3-CMC), also known as clophedrone, is a synthetic substance belonging to the cathinone class of psychoactive compounds. It is very similar in structure to other methcathinone derivatives such as 3-MMC and 4-CMC. Unlike cathinone, which occurs naturally in the khat plant Catha edulis, 3-CMC is not found in nature and is solely produced through chemical synthesis.
TH-PVP is a substituted cathinone derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Hungary in 2015, but has subsequently been found in numerous other countries around the world including Spain, Belgium, Poland, Turkey and Brazil.
3-Methoxymethcathinone (3-MeOMC), also known as meta-methoxymethcathinone (m-MeOMC), is a designer drug of the substituted cathinone family described as a stimulant.