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Methcathinone

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Methcathinone chemical structure
Methcathinone

2-(methylamino)-1-phenyl-propan-1-one
IUPAC name
CAS number
5650-44-2
ATC code

[[ATC_code_|]][1]

PubChem
1576
DrugBank
[2]
Chemical formula {{{chemical_formula}}}
Molecular weight 163.22 g/mol
Bioavailability
Metabolism
Elimination half-life
Excretion Urine
Pregnancy category
Legal status {{{legal_status}}}
Routes of administration Vaporized, insufflated, injected, orally


Methcathinone (2-(methylamino)-propiophenone, α-methylamino-propiophenone) is a psychoactive stimulant. It is sometimes used as a recreational drug and is considered to be 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 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. 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 due to its classification as a Schedule I substance. In contrast, methamphetamine has certain medical uses such as treatment of morbid obesity, narcolepsy, and ADHD.

HistoryEdit

Methcathinone was first synthesized in 1928.[2] 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.[3]

ChemistryEdit

Methcathinone is very similar in structure to ethcathinone, rare cathinone analogue and cathinone, a stimulant alkaloid occurring in the shrub Catha edulis (Khat), the synthetic stimulant methamphetamine, and other phenethylamines.

Methcathinone has a single chiral carbon atom, thus yielding enantiomeric + and - forms.

Methcathinone is most commonly made by the oxidation of ephedrine. Oxidation of ephedrine to methcathinone requires little chemistry experience, making it easy to synthesize. Potassium permanganate (KMnO4) is most commonly used as the oxidant.[4]

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.[5] If done in a proper laboratory using the proper procedures, however, potassium permanganate can be a high-yielding reactant.[4]

Methcathinone as free base is very unstable; it easily loses its ketone status and converts back into an alcohol. 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.

Methcathinone acts on the body and brain much like methamphetamine and amphetamines do.

Effects Edit

Methcathinone hydrochloride increases spontaneous rodent locomotor activity[6], potentiates the release of dopamine from dopaminergic nerve terminals in the brain[6], and causes appetite suppression.[How to reference and link to summary or text] Users can easily forget to consume fluids and a state of thirst and dehydration is apparent.

The effects of methcathinone are similar to those of methamphetamine, initially deemed to be less intense by the inexperienced user, and often more euphoric. 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
  • Rapid breathing
  • 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 (ie. one might spend days thinking that he or she is being productive but later realize that the activity and/or product was not even necessary)

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

Use and pharmacologyEdit

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.[7]

Anecdotal reports have provided some information on patterns of methcathinone use. The most common route of administration is via nasal insufflation (snorting).[How to reference and link to summary or text] Other routes of administration include oral ingestion, intravenous 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 "crash" characterized by long periods of sleep, excess eating and, in some cases, depression.[How to reference and link to summary or text]

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.[8]

Street namesEdit

Street slang for methcathinone may include terms such as Cat, Jeff, Bathtub Speed, Wannabe-Speed, Kitty, Meth's Cat, or Meth's Kitten.

In Europe, methcathinone is primarily known as Ephedrone.

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

In South Africa it is primarily known as CAT or occasionally KAT. There, it is also confused (via name alone, not presentation) with Khat (sometimes spelled Qat). Another confusing name is that given to Tik - the local name for methamphetamine.

AddictionEdit

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

Methcathinone can be highly psychologically addictive, and can produce methamphetamine-like withdrawals, 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. Racemic methcathinone hydrochloride is intravenously self-administered by baboons, thus indicating that methcathinone produces reinforcing effects in this laboratory animal, and suggesting that the drug has a potential for abuse in the human population.

Clinical useEdit

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,[9] with no clinical uses.

Furthermore, anecdotal reports from USENET posts in the 1990s indicates methcathinone doesn't have the inhibitory effects seen in other stimulants that make them useful as medications to treat Attention Deficit Hyperactivity Disorder.

See alsoEdit

Other related phenethylamine drugs and plants:

Other CNS-active phenyl-ethylamino ketones (Drugs that contain the cathinone core structure):

External linksEdit

ReferencesEdit

  1. Calkins RF, Aktan GB, Hussain KL. "Methcathinone: the next illicit stimulant epidemic?" J Psychoactive Drugs. 1995 Jul-Sep;27(3):277-85. PMID 8594170
  2. Hyde JF, Browning E, Adams R. "Synthetic Homologs of d,l-Ephedrine" Journal of the American Chemical Society. 1928;50(8):2287-2292. DOI:10.1021/ja01395a032
  3. Erowid
  4. 4.0 4.1 Methcathinone HCl FAQ v2.2
  5. http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/methcathinone.txt
  6. 6.0 6.1 Glennon RA, Yousif M, Naiman N, Kalix P (1987). Methcathinone: a new and potent amphetamine-like agent. Pharmacol. Biochem. Behav. 26 (3): 547–51.
  7. 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 Theraputics 307 (1).
  8. de Bie RM, Gladstone RM, Strafella AP, Ko JH, Lang AE. "Manganese-induced Parkinsonism associated with methcathinone (Ephedrone) abuse." Archives of Neurology. 2007 Jun;64(6):886-9 PMID 17562938
  9. The Misuse of Drugs Act 1971 (Modification) Order 1998 (SI 1998 No. 750). Statutory Instrument. Ministry of Justice (United Kingdom. URL accessed on 2008-07-06.
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