Methcathinone

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Methcathinone
Systematic (IUPAC) name
2-(methylamino)-1-phenyl-propan-1-one
Identifiers
CAS number	5650-44-2
ATC code	?
PubChem	1576
Chemical data
Formula	C₁₀H₁₃N O
Mol. mass	163.22
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	Urine
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule I (USA)
Routes	Vaporized, Insufflated, Injected, Taken Orally

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Unethical uses:

Other uses:

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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 in its ability to act as an serotonin reuptake inhibitor. Nevertheless, it is a potent CNS stimulant and dopamine reuptake inhibitor. 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.

Methcathinone is currently not a widely used drug in the United States; however, it is particularly popular in Michigan's Upper Peninsula, where it is most commonly produced^{[citation needed]}. This is notably because a student of the University of Michigan started synthesizing methcathinone with his friends. Unlike methamphetamine, it is flat-out illegal, being Schedule 1, whereas methamphetamine has certain medical uses such as treatment of life-threatening obesity, narcolepsy, and ADHD. Ironically, it is not as widely used illegaly, although it can be made from the same materials as meth but significantly easier, and requiring relatively little chemistry knowledge. Also it is a forgiving process, meaning that if something's not exactly right, it is less likely that it will destroy the batch.

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

[edit] 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 informed the UN Secretary-General of its opinion that methcathinone should be added to Schedule I of the Convention on Psychotropic Substances.^[1]

[edit] 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 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 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 replaced with a C-OH bond. In other words, basic methcathinone will convert back to the ephedrine it was synthesized from if not given an acid to bond to.

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

[edit] Effects

Methcathinone hydrochloride increases spontaneous rodent locomotor activity, potentiates the release of dopamine from dopaminergic nerve terminals in the brain, and causes appetite suppression. 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 in relation to importances of matters (might spend days thinking that is being productive achieving something but later might realize that the product was not even necessary at all.)

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

Methcathinone's effects differ in various characteristic ways to that of methamphetamine. The effects seem to be of somewhat similar intensity to methamphetamine, differing in the nature of the shiny white effect which characterises the first few methamphetamine uses, and the dopamine and serotonin effects are quite apparent and also produce a shiny white effect which is quite different to that of methamphetamine and is more localized to the head.

The first time user often makes the mistake of thinking that methcathinone is less powerful than cocaine or methamphetamine. The experience is governed by factors such as quantity of dosing (initial build up) and the dose and interval used between maintenance. The effect of methcathinone has been described as somewhere between coffee and cocaine. This comparison is completely inaccurate and might be expressed by the first time user or one who is converting from cocaine. The sudden burst of euphoria and then sudden fall as experienced by cocaine users does not occur on methcathinone causing some users to prefer cocaine. The effects of methcathinone are closest to that of methamphetamine.

Another difference between methamphetamine and methcathinone is that tolerance seems to build up faster for methamphetamine than for methcathinone and the recovery period from methcathinone is faster, both in terms of physically recovery, and also in terms of magnitude of highs.

Methcathinone has a mild yet distinct hallucinogenic quality especially at higher doses and when aggravated by sleep deprivation.

[edit] 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 of 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.

[edit] Street names

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

In Europe, methcathinone is primarily known as Ephedrone.

In (Australia): Goey, Speed, Gas, Go, Tweak (primarily distributed in a gel-like form measured in points(1/10 of a gram); although it can be "cut" -(mixed with) epsom salts and other products) which then usually turn the substance into a powder based form and/or to a liquid)-

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

[edit] 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 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.

[edit] 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.