Methcathinone

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Methcathinone
Methcathinone skeletal.svg
Methcathinone-3d-CPK.png
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 YesY
Chemical data
Formula C10H13NO 
Mol. mass 163.22 g/mol
 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[edit]

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 Эфедронephedrone). 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[edit]

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[edit]

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[edit]

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 Rβ-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[edit]

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[edit]

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[disambiguation needed] 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[edit]

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

See also[edit]

References[edit]

  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". Pharmacol. Biochem. Behav. 47 (4): 981–3. doi:10.1016/0091-3057(94)90307-7. PMID 8029273. 
  12. ^ "https://www.unodc.org/pdf/convention_1971_en.pdf". United Nations Office on Drugs and Crime. Retrieved 9 January 2013. 
  13. ^ http://www.drugfree.org/drug-guide/methcathinone
  14. ^ "The Misuse of Drugs Act 1971 (Modification) Order 1998 (SI 1998 No. 750)". Statutory Instrument. Ministry of Justice. 1998-03-18. Retrieved 2008-07-06. 

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