![Substituted cathinone](https://upload.wikimedia.org/wikipedia/commons/d/d7/Substituted_cathinone.svg)
Substituted cathinones, which include some
stimulants and
entactogens, are derivatives of
cathinone. They feature a
phenethylamine core with an
alkyl
In organic chemistry, an alkyl group is an alkane missing one hydrogen.
The term ''alkyl'' is intentionally unspecific to include many possible substitutions.
An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...
group
A group is a number of persons or things that are located, gathered, or classed together.
Groups of people
* Cultural group, a group whose members share the same cultural identity
* Ethnic group, a group whose members share the same ethnic ide ...
attached to the
alpha carbon
In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule.
Numeric locants
The International Union of Pure and Applied Chemistry (IUPAC) recommends the us ...
, and a
ketone group attached to the
beta carbon
In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule.
Numeric locants
The International Union of Pure and Applied Chemistry (IUPAC) recommends the use of ...
, along with additional
substitutions. Cathinone occurs naturally in the plant
khat
Khat or qat ( ''ch’at''; Oromo: ''Jimaa'', so, qaad, khaad, khat or chat, ar, القات ''al-qāt'') is a flowering plant native to eastern and southern Africa. Khat contains the alkaloid cathinone, a stimulant, which is said to cause e ...
whose leaves are chewed as a recreational drug.
List of substituted cathinones
The derivatives may be produced by substitutions at four locations of the cathinone molecule:
* R
1 = hydrogen, or any combination of one or more alkyl, alkoxy, alkylenedioxy, haloalkyl or halide substituents
* R
2 = hydrogen or any alkyl group
* R
3 = hydrogen, any alkyl group, or incorporation in a cyclic structure
* R
4 = hydrogen, any alkyl group, or incorporation in a cyclic structure
The following table displays notable derivatives that have been reported:
Legality
On 2 April 2010, the
Advisory Council on the Misuse of Drugs
The Advisory Council on the Misuse of Drugs (ACMD) is a British statutory advisory non-departmental public body, which was established under the Misuse of Drugs Act 1971.
Mandate
Its terms of reference, according to the Act, are as follows:
'' ...
in the
UK announced that a broad structure-based ban of this entire class of compounds would be instituted, following extensive publicity around grey-market sales and
recreational use
Recreational drug use indicates the use of one or more psychoactive drugs to induce an altered state of consciousness either for pleasure or for some other casual purpose or pastime by modifying the perceptions and emotions of the user. When a ...
of
mephedrone
Mephedrone, also known as , , and , is a synthetic stimulant drug of the amphetamine and cathinone classes. Slang names include drone, , White Magic, meow meow, bubble, ''txomin'' and yurrpt. It is chemically similar to the cathinone compounds ...
, a common member of the family. This ban covers compounds with the aforementioned general structure, with 28 compounds specifically named.
[Advisory Council on the Misuse of Drugs (UK)]
Consideration of the cathinones. 31 March 2010.
Retrieved 2011-07-17.
This text was added as an amendment to the
Misuse of Drugs Act 1971, to come into force on 16 April 2010. Note that four of the above compounds (cathinone, methcathinone, diethylpropion and pyrovalerone) were already illegal in the UK at the time the ACMD report was issued. Two compounds were specifically excluded from the ban, these being bupropion because of its common use in medicine and relative lack of abuse potential, and naphyrone because its structure falls outside the generic definition and not enough evidence was yet available to justify a ban.
Naphyrone analogues were subsequently banned in July 2010 following a further review by the ACMD, along with a further broad based structure ban even more expansive than the last.
![Naphyrone general](https://upload.wikimedia.org/wikipedia/commons/f/f4/Naphyrone_general.png)
The substitutions in the general structure for naphyrone analogues subject to the ban may be described as follows:
* Cyc = any monocyclic, or fused-polycyclic ring system (not being a phenyl ring or alkylenedioxyphenyl ring system), including analogues where the ring system is substituted to any extent with alkyl, alkoxy, haloalkyl or halide substituents, whether or not further substituted in the ring system by one or more other univalent substituents
* R
1 = hydrogen or any alkyl group
* R
2 = hydrogen, any alkyl group, or incorporation in a cyclic structure
* R
3 = hydrogen, any alkyl group, or incorporation in a cyclic structure
More new derivatives have however continued to appear, with the UK reporting more novel cathinone derivatives detected in 2010 than any other country in Europe, with most of them first identified after the generic ban had gone into effect and thus already being illegal despite never having been previously reported.
In the United States, substituted cathinones are the psychoactive ingredients in "
bath salts
Bath salts are water-soluble, pulverized minerals that are added to water to be used for bathing. They are said to improve cleaning, enhance the enjoyment of bathing, and serve as a vehicle for cosmetic agents. Bath salts have been developed wh ...
" which as of July 2011 were banned by at least 28 states, but not by the federal government.
See also
*
Markush structure
A Markush structure is a representation of chemical structure used to indicate a group of related chemical compounds. They are commonly used in chemistry texts and in patent claims. Markush structures are depicted with multiple independently var ...
*
Substituted amphetamines
*
Substituted methylenedioxyphenethylamine
Substitution reaction, Substituted methylenedioxy- phenethylamines (MDxx) are a large chemical class of derivative (chemistry), derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelic drug, ...
s
*
Substituted phenethylamine
Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by ...
s
*
Substituted phenylmorpholines
*
Structural scheduling of synthetic cannabinoids To combat the illicit synthetic cannabinoid industry many jurisdictions have created a system to control these cannabinoids through their general (or Markush) structure as opposed to their specific identity. In this way new analogs are already cont ...
*
Arylcyclohexylamine
Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.
History
Phencyclidine (PCP) is believed to be the first arylcyclohexylamine with recog ...
s
*
List of aminorex analogues
This is a list of aminorex analogues. Aminorex itself is a stimulant drug with a 5-phenyl-2-amino-oxazoline structure. It was developed in the 1960s as an anorectic, but withdrawn from sale after it was discovered that extended use produced pulmon ...
*
List of fentanyl analogues
*
List of methylphenidate analogues
References
{{Dopaminergics
Chemical classes of psychoactive drugs
Cathinones