Substituted cathinone

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Substitutive structure of a cathinone molecule.

Substituted cathinones, also known as cathinones, are a class of chemicals that include compounds with psychoactive effects. Cathinone itself is an endogenous monoamine alkaloid found in the plant Catha edulis (Khat), which is used by many communities in the horn of Africa and Arabian Peninsula as a mild stimulant, along with the compound cathine. Cathinones behave as central nervous system stimulants and are structurally related to amphetamines.

Chemistry

Substituted cathinones are a chemical class based upon the molecule cathinone. Cathinones are a sub-category of amphetamines. They share the core amphetamine structure, but are differentiated from substituted amphetamines by a ketone substitution on the beta carbon of the amphetamine structure. Thus, some cathinones, such as βk-MDMA, that differ from a popular substituted amphetamine by the beta ketone substitution, will take the name of the substituted amphetamine, with a "beta-keto"/"βk-" prefix. It should be noted that, although not technically substituted cathinones as they lack the alpha carbon methyl group present in cathinone, there exists a class of psychoactive compounds that differ from various substituted phenethylamines by a beta ketone substitution; most notably βk-2C-B.

Pharmacology

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The substituted cathinone class of entactogenic and stimulant drugs works via their action as a dopamine reuptake inhibitor. The agonism of this set of receptors leads to an increased rate firing of the post-synaptic neuron, triggering both cognitive and physical stimulation within the user.

List of substituted cathinones

Compound R2 R3 R4 R5 Rα RN1 RN2 Structure
Cathinone H H H H CH3 H H Cathinone.svg
Methcathinone H H H H CH3 H CH3 Methcathinone.svg
Ethcathinone H H H H CH3 H CH2CH3 Ethylcathinone.svg
3-MMC H CH3 H H CH3 H CH3 3-MMC.svg
Mephedrone (4-MMC) H H CH3 H CH3 H CH3 Mephedrone.svg
4-MEC H H CH3 H CH3 H CH2CH3 4-MEC.svg
3-CMC H Cl H H CH3 H CH3 3-CMC.svg
4-CMC H H Cl H CH3 H CH3 4-CMC.svg
Buphedrone H H H H CH2CH3 H CH3 Buphedrone.svg
Pentedrone H H H H CH2CH2CH3 H CH3 Pentedrone.svg
N-ethyl-nor-pentedrone (NEP) H H H H CH2CH2CH3 H CH2CH3 N-ethyl-nor-pentedrone.svg
Hexedrone H H H H CH2CH2CH2CH3 H CH3 Hexedrone.svg
N-ethyl-nor-hexedrone (Hexen) H H H H CH2CH2CH2CH3 H CH2CH3 N-ethyl-nor-hexedrone.svg
Heptedrone H H H H CH2CH2CH2CH2CH3 H CH3 Heptedrone.svg
N-ethyl-nor-heptedrone H H H H CH2CH2CH2CH2CH3 H CH2CH3 N-ethyl-nor-heptedrone.svg
4-ethylpentedrone H H CH2CH3 H CH2CH2CH3 H CH3 4-ethylpentedrone.svg
4-methyl-NEP H H CH3 H CH2CH2CH3 H CH2CH3 4-methyl-NEP.svg
α-PVP H H CH3 H CH2CH2CH3 CH2CH2- CH2CH2- Α-PVP.svg
α-PHP H H CH3 H CH2CH2CH2CH3 CH2CH2- CH2CH2- Α-PHP.svg
α-PHpP (PV8) H H CH3 H CH2CH2CH2CH3 CH2CH2- CH2CH2- Α-PHpP.svg
Mexedrone H H CH3 H CH2OCH3 H CH3 Mexedrone.svg
Methylone H O-CH2- O- H CH3 H CH3 Methylone.svg
Ethylone H O-CH2- O- H CH3 H CH2CH3 Ethylone.svg
Butylone H O-CH2- O- H CH2CH3 H CH3 Butylone.svg
Pentylone H O-CH2- O- H CH2CH2CH3 H CH3 Pentylone.svg
N-ethyl-nor-pentylone H O-CH2- O- H CH2CH2CH3 H CH2CH3 N-ethyl-nor-pentylone.svg
MDPV H O-CH2- O- H CH2CH2CH3 CH2CH2- CH2CH2- MDPV.svg

See also

References

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