Methcathinone
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{{Refimprove|date=July 2007}}
{{Drugbox|
|IUPAC_name = 2-(methylamino)-1-phenyl-propan-1-one
| image=Methcathinone skeletal.svg
| image2=Methcathinone-3d-CPK.png
| CAS_number=5650-44-2
| CAS_supplemental = {{CAS|49656-78-2}} ([[hydrochloride|HCL]])<br>{{CAS|112117-24-5}} (S form)<br>{{CAS|66514-93-0}} ( S [[hydrochloride|HCL]])
| ATC_prefix=
| ATC_suffix=
| ATC_supplemental=
| PubChem=1576
| DrugBank=
| C=10 | H=13 | N=1 | O=1
| molecular_weight = 163.22 g/mol
| bioavailability=
| metabolism =
| elimination_half-life=
| excretion = [[Urine]]
| pregnancy_category =
| legal_US = Schedule I
| routes_of_administration= [[Vaporize]]d, [[Wiktionary:insufflation|insufflated]], [[Intravenous infusion|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]]<ref name="calkins 2005">Calkins RF, Aktan GB, Hussain KL. "Methcathinone: the next illicit stimulant epidemic?" ''J Psychoactive Drugs''. 1995 Jul-Sep;27(3):277-85. PMID 8594170</ref>. It is usually snorted, but can be smoked, injected, or taken orally. Methcathinone is currently a [[Drug Enforcement Administration|DEA]] [[Schedule I (US)|Schedule I]] controlled substance in the [[United States]].
The C=O bond at the ''R<sub>β</sub>''-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]].
==History==
Methcathinone was first synthesized in Germany in 1928. 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]].<ref>[http://www.erowid.org/chemicals/chemicals_law1.shtml Erowid]</ref>
==Chemistry==
Methcathinone is very similar in structure to [[ethcathinone]], rare cathinone analogue and [[cathinone]], a [[stimulant]] [[alkaloid]] occurring in the [[shrub]] ''[[Catha edulis]]'' ([[Khat]]), the [[chemical synthesis|synthetic]] [[stimulant]] [[methamphetamine]], and other [[phenethylamine]]s.
Methcathinone has a single [[chiral carbon]] atom, thus yielding [[enantiomer]]ic + 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]] (KMnO<sub>4</sub>) is most commonly used as the oxidant.<ref>[http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/methcatfaq.22.html Methcathinone HCl FAQ v2.2<!-- Bot generated title -->]</ref>
Synthesizing methcathinone using either potassium permanganate or various [[chromate]]s 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]].<ref>http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/methcathinone.txt</ref> If done in a proper laboratory using the proper procedures, however, potassium permanganate can be a high-yielding reactant.<ref>[http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/methcatfaq.22.html Methcathinone HCl FAQ v2.2<!-- Bot generated title -->]</ref>
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 ==
Methcathinone hydrochloride increases spontaneous rodent [[locomotor]] activity<ref name="pmid3575369">{{cite journal |author=Glennon RA, Yousif M, Naiman N, Kalix P |title=Methcathinone: a new and potent amphetamine-like agent |journal=Pharmacol. Biochem. Behav. |volume=26 |issue=3 |pages=547–51 |year=1987 |pmid=3575369 |doi=10.1016/0091-3057(87)90164-X}}</ref>, potentiates the release of [[dopamine]] from [[dopaminergic]] [[nerve]] terminals in the [[brain]]<ref name="pmid3575369">{{cite journal |author=Glennon RA, Yousif M, Naiman N, Kalix P |title=Methcathinone: a new and potent amphetamine-like agent |journal=Pharmacol. Biochem. Behav. |volume=26 |issue=3 |pages=547–51 |year=1987 |pmid=3575369 |doi=10.1016/0091-3057(87)90164-X}}</ref>, and causes [[appetite suppression]].{{Fact|date=April 2007}} 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 (emotion)|euphoria]]
* Increased alertness
* Dilated [[pupil]]s
* 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 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.<ref>{{cite journal | author = Rothman, B. R. et al | title = In Vitro Characterization of Ephedrine-Related Stereoisomers at Biogenic Amine Transporters and the Receptorome Reveals Selective Actions as Norepinephrine Transporter Substrates | journal = The Journal of Pharmacology and Experimental Theraputics | volume = 307 | issue = 1 | date = June 2003 | unused_data = |PMID 12954796}}</ref>
Anecdotal reports have provided some information on patterns of methcathinone use. The most common [[route of administration]] is via [[Nose|nasal]] [[Wiktionary:insufflation|insufflation]] ([[Wiktionary:snorting|snorting]]).{{Fact|date=April 2007}} Other routes of administration include [[oral ingestion]], [[intravenous injection]] and [[Tobacco smoking|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, [[clinical depression|depression]].{{Fact|date=April 2007}}
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]].<ref>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</ref>
==Street names==
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]].
==Addiction==
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 [[psychoactive drug|drug]] [[discrimination]] studies, methcathinone hydrochloride evokes responses similar to those induced by both [[Amphetamine|(+)-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 [[intravenous]]ly self-administered by [[baboon]]s, 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 use==
In the US, methcathinone is listed as a [[Schedule I (US)|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,<ref>{{cite web|url=http://www.statutelaw.gov.uk/content.aspx?ActiveTextDocId=2810429|title=The Misuse of Drugs Act 1971 (Modification) Order 1998 (SI 1998 No. 750)|date=1998-03-18|work=[[Statutory Instrument (UK)|Statutory Instrument]]|publisher=[[Ministry of Justice (United Kingdom)|Ministry of Justice]]|accessdate=2008-07-06}}</ref> with no clinical uses.
Furthermore, anecdotal reports from [[USENET]] posts in the 1990s indicate that unlike many stimulants, methcathinone doesn't have the inhibitory effects seen in other stimulants that make them useful as medications to treat [[Attention Deficit Hyperactivity Disorder]].
==See also==
Other related phenethylamine drugs and plants:
* [[Khat]] (contains [[cathinone]] and [[cathine]])
* [[Methamphetamine]]
* [[Phenethylamine]]
* [[Ephedrine]]
* [[Pseudoephedrine]]
* [[Phenylpropanolamine]]
Other CNS-active phenyl-ethylamino ketones (Drugs that contain the [[cathinone]] core structure):
* [[Diethylcathinone]] ([[Tenuate]])
* [[Ethcathinone]]
* [[Dimethylcathinone]]
* [[Bupropion]] (''Wellbutrin'', ''Zyban'')
* [[Methylenedioxymethcathinone|Methylone]]
* [[Methoxyphedrine|Methedrone]]
* [[Mephedrone]]
==External links==
* [http://www.erowid.org/chemicals/cathinone/cathinone.shtml Cathinone & Methcathinone from Erowid]
* [http://paranoia.lycaeum.org/stimulants/59.FR.31639 Methcathinone from lycaeum]
==References==
{{reflist}}
* [http://www.erowid.org/chemicals/chemicals_law1.shtml International Drug Scheduling; Convention on Psychotropic Substances; Certain Stimulant/Hallucinogenic Drugs and Certain Nonbarbiturate Sedative Drugs], Food and Drug Administration, June 20, 1994.
{{Phenethylamines}}
[[Category:Alkaloids]]
[[Category:Amphetamines]]
[[Category:Class A drugs]]
[[Category:Class B drugs]]
[[Category:Stimulants]]
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[[pl:Metylokatynon]]