Methcathinone

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Methcathinone is a stimulant drug. It is sometimes used as a recreational drug and is considered to be addictive. 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. Its effects differ slightly from the amphetamines especially its ability to act as a serotonin agonist. Nevertheless, it is a potent CNS stimulant and dopamine agonist. Chronic high dosage abuse may result in acute mental confusion ranging from mild paranoia to psychosis. These symptoms typically disappear quickly if use is stopped.

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Image:Methcathinone 2D Structure.gif Methcathinone
IUPAC name: 2-(methylamino)-I-phenyl-propan-1-one
CAS number 5650-44-2	ATC code ?
Chemical formula	C₁₀H₁₃N O
Molecular weight	163.22
Bioavailability	?
Metabolism	?
Elimination half life	?
Excretion	Urine
Pregnancy category	?
Legal status	Schedule I (USA)
Delivery	Vaporized, Insufflated, Injected, Taken Orally

Indicated for:

Recreational uses:

Unethical uses:

Other uses:

Contraindications:

Side effects:

Severe:

Atypical sensations:

Cardiovascular:

Ear, nose, and throat:

Endocrinal:

Eye:

Gastrointestinal:

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Musculo skeletal:

Neurological:

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Urogenital and reproductive:

Miscellaneous:

1 History
2 Chemistry
3 Effects
4 Use and pharmacology
5 Street names
6 Addiction
7 Clinical use
8 See also
9 External links
10 References

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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 Soviet Union.

Circa 1994, the United States government informed the UN Secretary-General of its opinion that methcathinone should be added to Schedule I of the Convention on Psychotropic Substances [1].

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Chemistry

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

Methcathinone has a single asymmetric carbon atom, thus yielding enantiomeric + and - forms. Chemical Abstract Services registry numbers for the racemic base and hydrochloride forms are 5650-44-2 and 49656-78-2, respectively. The Chemical Abstract Services registry numbers for the base and hydrochloride forms of the S absolute stereochemical configuration are 112117-24-5 and 66514-93-0, respectively.

Various names for methcathinone include:

2-(methylamino)-propiophenone
α-methylamino-propiophenone

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 (K Mn O₄) is most the commonly used as the oxidant.

Methcathinone can also be synthesized via the oxidation of ephedrine using sodium dichromate and sulfuric acid. This process is just as simple as oxidizing the ephedrine with potassium permanganate.

Synthesizing methcathinone from either potassium permanganate or various chromates is considered undesirable because of the low yields. A method that yields more methcathinone is oxidizing ephedrine with sodium hypochlorite. If done in a proper laboratory using the proper procedures, however, potassium permanganate can be a high-yielding reactant.

Methcathinone acts on the body & brain much like methamphetamine & amphetamine do.

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Effects

Methcathinone hydrochloride increases spontaneous rodent locomotor activity, potentiates the release of radio-labelled dopamine from dopaminergic nerve terminals in the brain, and causes appetite suppression.

The effects of methcathinone are similar to those of methamphetamine, but generally less intense, 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

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

Methcathinone's effects have also been characterized as 'somewhat less intense than methamphetamine', and 'between caffeine and methamphetamine'.

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Use and pharmacology

Methcathinone is usually sold in quantities of one fourth of a gram, 1 gram, 3.5 grams ("8-ball") or an ounce (28.35 grams). The powdered material comes packaged in paper packets (called bindles), vials and plastic bags. Street prices are in the vicinity of $20.00 USD to $25.00 USD for one fourth of a gram, $100.00 USD for 1 gram, and $200 USD to $250.00 USD for 3.5 grams.

Anecdotal reports have provided some information on patterns of methcathinone abuse. The most common route of administration is via nasal insufflation (snorting). Other routes of administration include oral ingestion, intravenous injection and smoking.

Methcathinone is abused in binges lasting two to six days. During binges experienced users will administer methcathinone at doses ranging from one-sixteenth to one-fourth or a gram. The interval between dosing varies between approximately 20 minutes and two hours. With such a dosing regimen, during a binge methcathinone may be administered in daily amounts exceeding 1 or 2 grams. The principal determinant defining the length of the binge is the amount of drug available; that is, the binge ends only when the available supply of drug runs out.

The methcathinone binge resembles amphetamine binges in that the abuser does 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.

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Street names

Cat, Jeff, Bathtub Speed, Wannabe-Speed, Kitty, Meth's Cat, Meth's Kitten

In Europe, methcathinone is primarily known as Ephedrone.

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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. 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 sulphate 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.

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Clinical use

As a Schedule-1 drug, there is no legal clinical use. Research without a specific DEA permit is prohibited.

Furthermore, anecdotal reports from USENET posts in the 1990s indicate that unlike many stimulants, Methcathinone probably doesn't have the inhibitory effects (mediated by norepinephrine) seen in other stimulants that make them useful as medications to treat Attention Deficit Hyperactivity Disorder.

It does promote weight loss in a manner similar to its sister drug methamphetamine, but unlike methamphetamine, cannot be prescribed by any doctor, for any reason, due to its legal classification.

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