Methcathinone/ˌmɛθˈkæθɪˌnoʊn/ (α-methylamino-propiophenone orephedrone) (sometimes called "cat" or "jeff" or "catnip" or "M-Kat" or "kat" or "intash") is amonoaminealkaloid andpsychoactivestimulant, a substitutedcathinone. It is used as arecreational drug due to its potent stimulant andeuphoric effects and is considered to beaddictive, with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration.[2] It is usuallysnorted, but can be smoked, injected, or taken orally.
Methcathinone is listed as aSchedule I controlled substance by theConvention on Psychotropic Substances and theUnited States'Controlled Substances Act, and as such it is not considered to be safe or effective in the treatment, diagnosis, prevention, or cure of any disease, and has no approved medical use. Possession and distribution of methcathinone for the purpose of human consumption is illegal under any/all circumstances in the United States and is either illegal or highly regulated in most jurisdictions worldwide.
Methcathinone was first synthesized in 1928 in the United States[3] and was patented byParke-Davis in 1957.[4] It was used in theSoviet Union during the 1930s and 1940s as ananti-depressant (under the nameЭфедрон—ephedrone). Methcathinone has long been used as a drug of abuse in theSoviet Union andRussia.[citation needed]
It is currently a Schedule III drug in Canada along with codeine, anabolic steroids, and testosterone. It is legal to possess in Canada, but illegal to purchase. Methcathinone used to have the nick-name "bath salts", to avoid restrictions on importation.
Methcathinone is a beta-ketoN-methylamphetamine and is closely related to the naturally occurring compounds,cathinone andcathine. It is also very closely related tomethamphetamine, differing by only the β-ketone substituent and differing fromamphetamine by both a keto and N-methyl substituent. Its carbon skeleton is identical to pseudoephedrine and methamphetamine. It differs from pseudoephedrine in that the hydroxyl beta to the aromatic ring is oxidized to a ketone.
Methcathinone possesses achiral carbon atom, and thereforetwo enantiomers are possible. When it is made semi-synthetically from pseudo/ephedrine as a starting material, then only a single enantiomer is produced. Given that the chiral center has analpha hydrogen and adjacent the carbonyl group, the molecule willracemize in solution via anenol intermediate. This process is known asketo–enol tautomerism.
In clandestine laboratories, synthesizing methcathinone using potassium permanganate is considered undesirable because of the low yields and the high toxicity of this oxidant(seeManganese toxicity); however, if done in a proper laboratory using the proper procedures potassium permanganate can be a high-yielding reactant. A method that yields more methcathinone is oxidizing (pseudo)ephedrine withchromium (VI) compounds, which are far more toxic than permanganate compounds.
Methcathinone as free base is very unstable; it easily loses itsketone group, which is substituted with ahydroxyl group, yieldingpseudoephedrine, in the reverse of the typical synthesis reaction. Structurally, this occurs when the C=O bond at the Rβ-position is converted into a C-OH bond. Additionally, a dimerization reaction has been observed in solutions of freebase methcathinone, which yields a biologically inactive compound.[8]
Methcathinone binges resemble amphetamine binges in that the user may not sleep or eat, and takes in little in the way of liquids. The methcathinone binge is followed by long periods of sleep, excess eating, long-lasting nosebleeds (insufflation of methcathinone is corrosive to thenasal mucosa in the same manner as methamphetamine) and, in some cases,depression.[citation needed]
TheConvention on Psychotropic Substances lists methcathinone as a Schedule I substance which restricts its use for government-approved medical and scientific uses.[30]
Methcathinone is aSchedule 9 prohibited substance inAustralia under thePoisons Standard (February 2021).[31] A Schedule 9 substance is defined as a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[31]
Methcathinone is illegal inFinland. It is scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".[34]
^DeRuiter J, Hayes L, Valaer A, Clark CR, Noggle FT (1994). "Methcathinone and Designer Analogues: Synthesis, Stereochemical Analysis, and Analytical Properties".Journal of Chromatographic Science.32 (12):552–564.doi:10.1093/chromsci/32.12.552.
^abcRothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin".Synapse.39 (1):32–41.doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3.PMID11071707.
^abRothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA (October 2003). "In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates".The Journal of Pharmacology and Experimental Therapeutics.307 (1):138–145.doi:10.1124/jpet.103.053975.PMID12954796.S2CID19015584.
^Glennon RA, Dukat M (2017). "Structure-Activity Relationships of Synthetic Cathinones".Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. Springer. pp. 19–47.doi:10.1007/7854_2016_41.ISBN978-3-319-52442-9.PMC5818155.PMID27830576.
^Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, et al. (October 2003). "In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates".The Journal of Pharmacology and Experimental Therapeutics.307 (1):138–145.doi:10.1124/jpet.103.053975.PMID12954796.S2CID19015584.
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