Methcathinone

Methcathinone

Systematic (IUPAC) name
(RS)-2-(methylamino)-1-phenyl-propan-1-one
Clinical data
Pregnancy cat.	?
Legal status	Schedule I (US)
Routes	Vaporized, insufflated, injected, orally
Pharmacokinetic data
Excretion	Urine
Identifiers
CAS number	5650-44-2 Y (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	eMolecules & PubChem
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
Y(what is this?)  (verify)

Methcathinone (α-methylamino-propiophenone), is a psychoactive stimulant, sometimes used as a recreational drug and considered addictive.^[1] It is usually snorted, but can be smoked, injected, or taken orally. Methcathinone is currently a DEA Schedule I controlled substance in the United States.

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. 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. These symptoms typically disappear quickly if use is stopped.

Unlike methamphetamine, methcathinone is not legal under any circumstances in the US due to its classification as a Schedule I substance. Conversely, methamphetamine has certain approved medical uses such as treatment of morbid obesity, narcolepsy and ADHD.

History

Methcathinone was first synthesized in 1928 in the United States^[2] and finally patented by Parke Davis in 1957^[3]. It was used in the Soviet Union during the 1930s and 1940s as an anti-depressant. Since the 1960s, methcathinone has been used as a recreational drug in the (former) Soviet Union.

Circa 1994, the United States government recommended to the UN Secretary-General that methcathinone should be added to Schedule I of the Convention on Psychotropic Substances.^[4]

Chemistry

Methcathinone is N-methylcathinone whereas cathine is N-demethylpseudoephedrine (SS), all of which are stimulant alkaloids found in the shrub Catha edulis (Khat). Stimulants such as meth/amphetamine, and other phenethylamines are also similar in structure.

Methcathinone possesses a chiral carbon atom, and therefore two enantiomers are possible. When it is made semi-synethically 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 is "most commonly" made by 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 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
• Loss of cognitive ability relating to the distinction of relative importance of matters

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

Use and pharmacology

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

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.

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]

Street names

Street slang for methcathinone may be confused with methylmethcathinone (mephedrone) and terms may be used interchangeably and include terms such as MCat (pronounced "em-kat"), Cat, Meow, Stroof, Katestroof, Jeff, Bathtub Speed, Wannabe-Speed, Kitty, Meth's Cat, Meth's Kitten or Marzipan (from smell during synthesis).

In Europe, methcathinone is primarily known as Ephedrone.

In the United Kingdom, methcathinone may be known as M-cat (though this can also refer to the chemical 4-methylmethcathinone; known as mephedrone).

In Australia, methcathinone may be known as ketone or bk (beta ketone).

In South Africa it is known as Cat, Ietsies kayo, gram or line. There, it is also confused (via name alone, not presentation) with Khat (sometimes spelled Qat).

In Bulgaria it is known as PIKO.

In Poland it is known as Kot (cat)

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. It is highly unlikely for a methcathinone user to experience addiction on their first or even several subsequent administrations of the drug.

In drug discrimination studies, methcathinone hydrochloride evokes responses similar to those induced by both (+)-amphetamine sulfate and cocaine hydrochloride. When examined in particular pharmacological assays for psychomotor stimulant-like activity, both the d and l 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 (+)-amphetamine.

Clinical use

In the US, methcathinone is listed as a Schedule I drug, for which there is no clinical use. Research in the United States without a specific DEA permit is also prohibited. In the Netherlands, methylcathinone is listed as a Level I substance of the Opium Law, for which there is no clinical use. In the UK, methcathinone is listed as a Class B drug,^[12] with no clinical uses.

See also

• Substituted cathinone

References

1. ^ Calkins RF, Aktan GB, Hussain KL (1995). "Methcathinone: the next illicit stimulant epidemic?". Journal of psychoactive drugs 27 (3): 277–85. PMID 8594170. 
2. ^ Hyde JF, Browning E, Adams R (1928). "Synthetic Homologs of d,l-Ephedrine". Journal of the American Chemical Society 50 (8): 2287–2292. doi:10.1021/ja01395a032. 
3. ^ US Patent 2802865 -ETHYLAMINOPROPIOPHENONE COMPOUNDS
4. ^ Erowid
5. ^ http://www.scribd.com/doc/35411/The-Clandestine-Chemists-Notebook The Clandestine Chemists Notebook
6. ^ ^{a b} Methcathinone HCl FAQ v2.2
7. ^ http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/methcathinone.txt
8. ^ ^{a b} Glennon RA, Yousif M, Naiman N, Kalix P (1987). "Methcathinone: a new and potent amphetamine-like agent". Pharmacol. Biochem. Behav. 26 (3): 547–51. doi:10.1016/0091-3057(87)90164-X. PMID 3575369. 
9. ^ Rothman, B. R. et al. (June 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): 138–45. doi:10.1124/jpet.103.053975. PMID 12954796. 
10. ^ De Bie RM, Gladstone RM, Strafella AP, Ko JH, Lang AE (Jun 2007). "Manganese-induced Parkinsonism associated with methcathinone (Ephedrone) abuse". Archives of Neurology 64 (6): 886–9. doi:10.1001/archneur.64.6.886. PMID 17562938. 
11. ^ Kaminski BJ, Griffiths RR (April 1994). Intravenous self-injection of methcathinone in the baboon. 47. pp. 981–3. PMID 8029273. 
12. ^ "The Misuse of Drugs Act 1971 (Modification) Order 1998 (SI 1998 No. 750)". Statutory Instrument. Ministry of Justice. 1998-03-18. http://www.statutelaw.gov.uk/content.aspx?ActiveTextDocId=2810429. Retrieved 2008-07-06. 

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

External links

• Cathinone & Methcathinone from Erowid
• Methcathinone from lycaeum