Methcathinone

Methcathinone

Systematic (IUPAC) name
(RS)-2-(methylamino)-1-phenyl-propan-1-one
Clinical data
Legal status	Schedule I (US)
Routes	Vaporized, insufflated, injected, orally
Pharmacokinetic data
Excretion	Urine
Identifiers
CAS number	5650-44-2 N (R form) 49656-78-2 (R form · HCl) 112117-24-5 (S form) 66514-93-0 (S form · HCl)
ATC code	None
PubChem	CID 1576
ChemSpider	1519 Y
Chemical data
Formula	C10H13NO
Mol. mass	163.22 g/mol
SMILES O=C(c1ccccc1)C(NC)C
InChI InChI=1S/C10H13NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,11H,1-2H3 Y Key:LPLLVINFLBSFRP-UHFFFAOYSA-N Y
N (what is this?)  (verify)

Methcathinone (α-methylamino-propiophenone or ephedrone) (sometimes called "cat" or "jeff") is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational drug and considered to be addictive.^[1] 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.

History

Methcathinone was first synthesized in 1928 in the United States^[2] and was patented by Parke Davis in 1957.^[3] It was used in the Soviet Union during the 1930s and 1940s as an anti-depressant (under the name Эфедрон—ephedrone). Methcathinone has long been used as a drug of abuse in the Soviet Union and Russia.^{[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.^[4]

Chemistry

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.

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 centre is adjacent to the carbonyl group, the molecule will racemise in solution.

Methcathinone production utilizes the oxidation of ephedrine. Oxidation of ephedrine to methcathinone requires little chemistry experience, making it (relatively) easy to synthesize.^[5] Potassium permanganate (KMnO₄) is most commonly used as the oxidant.^[6]

In clandestine laboratories, synthesizing methcathinone using either potassium permanganate or various chromates is considered undesirable because of the low yields and the high toxicity of these oxidants. A method that yields more methcathinone is oxidizing ephedrine with sodium hypochlorite.^[7] If done in a proper laboratory using the proper procedures, however, potassium permanganate can be a high-yielding reactant.^[6]

Methcathinone as free base is very unstable; it easily loses its ketone and converts back into an alcohol.^{[citation needed]} Structurally, this occurs when the C=O bond at the Rβ-position is converted into a C-OH bond. In other words, basic methcathinone will turn into (& also metabolize to) ephedrine, from which it was synthesized.

Effects

Methcathinone hydrochloride increases spontaneous rodent locomotor activity,^[8] potentiates the release of dopamine from dopaminergic nerve terminals in the brain,^[8] and causes appetite suppression.^{[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.^{[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:

• Feelings of euphoria
• Increased alertness
• Dilated pupils
• Slurred speech
• Increased heart rate
• Inability to stop talking
• Increased empathy and sense of communication
• Both decreased and increased sexual function and desire

The effects of methcathinone usually last from four to six hours.

Pharmacology

Methcathinone has very strong affinities for the dopamine transporter and the norepinephrine (noradrenaline) transporter. Its affinity for the serotonin transporter is less than that of methamphetamine.^[9]

The C=O bond at the R_β-position (directly right of the benzene ring) is slightly polar, and as a result the drug does not cross the lipid blood–brain barrier quite as well as amphetamine.^{[citation needed]} Nevertheless, it is a potent CNS stimulant and dopamine reuptake inhibitor. Chronic high dosage use may result in acute mental confusion ranging from mild paranoia to psychosis.^{[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).^{[citation needed]} Other routes of administration include per os, IV injection and smoking.

Illicit usage

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 a "case of the Mondays" characterized by long periods of sleep, excess eating, long-lasting nosebleeds and, in some cases, depression.^{[citation needed]}

Injecting this substance has recently 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.^[10]

Addiction

In preclinical studies, methcathinone hydrochloride produces an abuse potential similar to that of the amphetamines.^[11]

Methcathinone can be highly psychologically addictive, and can produce a methamphetamine-like withdrawal, which is somewhat less in intensity than methamphetamine.^{[citation needed]}

In drug discrimination studies, methcathinone hydrochloride evokes responses similar to those induced by both dextroamphetamine sulfate and cocaine hydrochloride. When examined in particular pharmacological assays for psychomotor stimulant-like activity, both the dextrorotary and levorotary enantiomeric forms of methcathinone hydrochloride have been found to be pharmacologically active. In these assays, the l-form of methcathinone is more active than either d-methcathinone or dextroamphetamine.

Clinical use

The Convention on Psychotropic Substances lists methcathinone as a Schedule I substance.^[12]

• In the United States, methcathinone is listed as a Schedule I drug, for which there is no clinical use.^[13]
• In the Netherlands, methylcathinone is listed as a Level I substance of the Opium Law, for which there is no clinical use.
• In the United Kingdom, methcathinone is listed as a Class B drug with no clinical uses.^[14]

See also

• Substituted cathinone

References

External links

• Cathinone & Methcathinone from Erowid
• International Drug Scheduling; Convention on Psychotropic Substances; Certain Stimulant/Hallucinogenic Drugs and Certain Nonbarbiturate Sedative Drugs, Food and Drug Administration, June 20, 1994.
• Methcathinone from lycaeum