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Methcathinone Template:IPAc-en (α-methylamino-propiophenone or ephedrone) (sometimes called "cat" or "jeff" or "catnip" or "M-Kat" or "kat" or "intash") is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational drug due to its potent stimulant and euphoric effects and is considered to be addictive, with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration.<ref name="calkins 2005">Template:Cite journal</ref> It is usually snorted, but can be smoked, injected, or taken orally.

Methcathinone is listed as a Schedule I controlled substance by the Convention on Psychotropic Substances and the United 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.

HistoryEdit

Methcathinone was first synthesized in 1928 in the United States<ref name="hyde1928">Template:Cite journal</ref> and was patented by Parke-Davis in 1957.<ref>US Patent 2802865 -ETHYLAMINOPROPIOPHENONE COMPOUNDS</ref> It was used in the Soviet Union during the 1930s and 1940s as an anti-depressant (under the name Эфедронephedrone). Methcathinone has long been used as a drug of abuse in the Soviet Union and Russia.Template:Citation needed

Circa 1994, the United States government recommended to the UN Secretary-General that methcathinone should be listed as a Schedule I controlled substance in the Convention on Psychotropic Substances.<ref>Erowid</ref> In 1995, following US advice, China added the drug to its list of prohibited substances and discontinued its pharmaceutical use.<ref>Template:Cite news</ref>

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.

ChemistryEdit

Template:More citations needed section Methcathinone is a beta-keto N-methylamphetamine and is closely related to the naturally occurring compounds, cathinone and cathine. It is also very closely related to methamphetamine, differing by only the β-ketone substituent and differing from amphetamine 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 a chiral carbon atom, and therefore two 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 an alpha hydrogen and adjacent the carbonyl group, the molecule will racemize in solution via an enol intermediate. This process is known as keto–enol tautomerism.

Methcathinone production utilizes the oxidation of pseudoephedrine or ephedrine, the former being preferred because of much higher yields achieved. Oxidation of pseudoephedrine to methcathinone requires little chemistry experience, making it (relatively) easy to synthesize.<ref>The Clandestine Chemists Notebook</ref>Template:Unreliable source? Potassium permanganate (KMnO4) is most commonly used as the oxidant.

In clandestine laboratories, synthesizing methcathinone using potassium permanganate is considered undesirable because of the low yields and the high toxicity of this oxidant Template:Crossreference; 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 with chromium (VI) compounds, which are far more toxic than permanganate compounds.

Methcathinone as free base is very unstable; it easily loses its ketone group, which is substituted with a hydroxyl group, yielding pseudoephedrine, 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.<ref>Template:Cite journal</ref>

EffectsEdit

Methcathinone hydrochloride increases spontaneous rodent locomotor activity,<ref name="pmid3575369">Template:Cite journal</ref> potentiates the release of dopamine from dopaminergic nerve terminals in the brain,<ref name="pmid3575369" /> and causes appetite suppression.Template:Citation needed Users can easily forget to consume fluids leading to increased thirst and dehydration. The effects of methcathinone are similar to those of methamphetamine, initially deemed to be less intense by the inexperienced user, and often more euphoric.Template:Citation needed The effects have been compared to those of cocaine, since it commonly causes hypertension (elevated blood pressure) and tachycardia (elevated heart rate).

Reported effects include:Template:Medical citation needed

  • Feelings of euphoria
  • Increased alertness
  • Slurred speech
  • Shaking of the limbs
  • Increased heart rate
  • Increased blood pressure, risk of stroke or heart attack
  • Increased empathy and sense of communication
  • Both decreased and increased sexual function and desire
  • Bruxism

The effects of methcathinone usually last from four to six hours.Template:Citation needed

PharmacologyEdit

PharmacodynamicsEdit

Template:Nowrap
Compound Template:Abbrlink Template:Abbrlink Template:Abbrlink Ref
Phenethylamine 10.9 39.5 >10,000 <ref name="ReithBLoughHong2015">Template:Cite journal</ref><ref name="Forsyth2012" /><ref name="Blough2008" />
Amphetamine Template:Abbr Template:Abbr Template:Abbr Template:Abbr
Template:NbspTemplate:NbspDextroamphetamine 6.6–7.2 5.8–24.8 698–1,765 <ref name="RothmanBaumannDersch2001">Template:Cite journal</ref><ref name="BaumannPartillaLehner2013">Template:Cite journal</ref>
Template:NbspTemplate:NbspLevoamphetamine 9.5 27.7 Template:Abbr <ref name="Forsyth2012">Template:Cite journal</ref><ref name="Blough2008">Template:Cite book</ref>
Methamphetamine Template:Abbr Template:Abbr Template:Abbr Template:Abbr
Template:NbspTemplate:NbspDextromethamphetamine 12.3–13.8 8.5–24.5 736–1,292 <ref name="RothmanBaumannDersch2001" /><ref name="BaumannAyestasPartilla2012">Template:Cite journal</ref>
Template:NbspTemplate:NbspLevomethamphetamine 28.5 416 4,640 <ref name="RothmanBaumannDersch2001" />
Cathinone 23.6–25.6 34.8–83.1 6,100–7,595 <ref name="Blough2008" /><ref name="BloughDeckerLandavazo2019">Template:Cite journal</ref><ref name="FitzgeraldGannonWalther2024">Template:Cite journal</ref>
Template:NbspTemplate:NbspTemplate:Small-Cathinone 72.0 184 >10,000 <ref name="HutsellBaumannPartilla2016">Template:Cite journal</ref>
Template:NbspTemplate:NbspTemplate:Small-Cathinone 12.4–28 18–24.6 2,366–9,267 <ref name="RothmanVuPartilla2003">Template:Cite journal</ref><ref name="ShalabiWaltherBaumann2017">Template:Cite journal</ref><ref name="HutsellBaumannPartilla2016" />
Methcathinone 22–26.1 12.5–49.9 2,592–5,853 <ref name="Blough2008" /><ref name="BloughDeckerLandavazo2019" /><ref name="Shalabi2017">Template:Cite thesis</ref><ref name="WaltherShalabiBaumann2019">Template:Cite journal</ref><ref name="FitzgeraldGannonWalther2024" />
Template:NbspTemplate:NbspTemplate:Small-Methcathinone Template:Abbr Template:Abbr Template:Abbr <ref name="Davies2019">Template:Cite thesis</ref>
Template:NbspTemplate:NbspTemplate:Small-Methcathinone 13.1 14.8 1,772 <ref name="RothmanVuPartilla2003" /><ref name="GlennonDukat2017">Template:Cite book</ref>
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: <ref name="RothmanBaumann2003">Template:Cite journal</ref><ref name="RothmanBaumann2006">Template:Cite journal</ref>

Methcathinone is a norepinephrine–dopamine releasing agent (NDRA). Methcathinone has very strong affinities for the dopamine transporter (DAT) and the norepinephrine transporter (NET). Its affinity for the serotonin transporter (SERT) is less than that of methamphetamine.<ref>Template:Cite journal</ref>

The C=O bond at the Rβ-position (directly right of the phenyl ring) is slightly polar, and as a result the drug does not cross the lipid blood–brain barrier quite as well as amphetamine.Template:Citation needed Nevertheless, it is a potent central nervous system (CNS) stimulant and dopamine reuptake inhibitor. Chronic high dosage use may result in acute mental confusion ranging from mild paranoia to psychosis.Template:Citation needed These symptoms typically disappear quickly if use is stopped.

Anecdotal reports have provided some information on patterns of methcathinone use. The most common route of administration is via nasal insufflation (snorting).Template:Citation needed Other routes of administration include oral, IV injection and smoking.

Illicit usageEdit

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 the nasal mucosa in the same manner as methamphetamine) and, in some cases, depression.Template:Citation needed

AddictionEdit

In preclinical studies, methcathinone hydrochloride produces an abuse potential similar to that of the amphetamines.<ref>Template:Cite journal</ref>

Methcathinone can be highly psychologically addictive, and can produce a methamphetamine-like withdrawal.

In drug discrimination studies, methcathinone hydrochloride evokes responses similar to those induced by both [[Dextroamphetamine|dextroTemplate:Shyamphetamine sulfate]] and cocaine hydrochloride.

Intravenous usageEdit

Injecting this substance has been associated with symptoms similar to those seen in patients with Parkinson's disease (manganism) due to the compound manganese dioxide which is a byproduct of synthesis with permanganate.<ref>Template:Cite journal</ref>

Legal statusEdit

The Convention on Psychotropic Substances lists methcathinone as a Schedule I substance which restricts its use for government-approved medical and scientific uses.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

AustraliaEdit

Methcathinone is a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2021).<ref name=":0">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> 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.<ref name=":0" />

United KingdomEdit

In the United Kingdom, methcathinone is listed as a Class B drug with no clinical uses.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

United StatesEdit

In the United States, methcathinone is listed as a Schedule I drug, for which there is no clinical use.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

NetherlandsEdit

In the Netherlands, methcathinone is listed as a Level I substance of the Opium Law, for which there is no clinical use.

See alsoEdit

ReferencesEdit

Template:Reflist

External linksEdit

{{#invoke:Navbox|navbox}} Template:Monoamine releasing agents Template:Monoaminergic neurotoxins {{#invoke:Navbox|navbox}} Template:Chemical classes of psychoactive drugs