Substituted cathinone - PsychonautWiki
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Substitutive structure of a cathinone molecule.

Substituted cathinones (also known as cathinones or synthetic cathinones) are a chemical class of psychoactive compounds that are based on the structure of cathinone. The class is composed of all the derivative compounds of cathinone which can be formed by replacing, or substituting, one or more hydrogen atoms in the cathinone core structure with substituents. Examples include MDPV, mephedrone, methylone, and a-PVP.

Cathinone is the active constituent of khat (Catha edullis), a plant whose leaves are chewed on for stimulant effect. Cathinone is closely related in structure to amphetamine, differing solely by a ketone group on the beta carbon.

Contents

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  
Methcathinone H H H H CH3 H CH3  
Ethcathinone H H H H CH3 H CH2CH3  
2-MMC CH3 H H H CH3 H CH3  
3-MMC H CH3 H H CH3 H CH3  
4-MC H H CH3 H CH3 H H  
Mephedrone (4-MMC) H H CH3 H CH3 H CH3  
4-MEC H H CH3 H CH3 H CH2CH3  
3-CMC H Cl H H CH3 H CH3  
3-CEC H Cl H H CH3 H CH2CH3  
4-CMC H H Cl H CH3 H CH3  
4-CEC H H Cl H CH3 H CH2CH3  
Bupropion H H H Cl CH3 H C(CH3)3  
3-FMC H F H H CH3 H CH3  
Buphedrone H H H H CH2CH3 H CH3  
Pentedrone H H H H CH2CH2CH3 H CH3  
N-ethyl-nor-pentedrone (NEP) H H H H CH2CH2CH3 H CH2CH3  
Hexedrone H H H H CH2CH2CH2CH3 H CH3  
N-ethyl-nor-hexedrone (Hexen) H H H H CH2CH2CH2CH3 H CH2CH3  
Heptedrone H H H H CH2CH2CH2CH2CH3 H CH3  
N-ethyl-nor-heptedrone H H H H CH2CH2CH2CH2CH3 H CH2CH3  
4-ethylpentedrone H H CH2CH3 H CH2CH2CH3 H CH3  
4-methyl-NEP H H CH3 H CH2CH2CH3 H CH2CH3  
α-PPP H H H H CH3 CH2CH2- CH2CH2-  
α-PVP H H H H CH2CH2CH3 CH2CH2- CH2CH2-  
α-PHP H H H H CH2CH2CH2CH3 CH2CH2- CH2CH2-  
α-PHpP (PV8) H H H H CH2CH2CH2CH2CH3 CH2CH2- CH2CH2-  
4F-α-PVP H H F H CH2CH2CH3 CH2CH2- CH2CH2-  
Mexedrone H H CH3 H CH2OCH3 H CH3  
Methylone H O-CH2- O- H CH3 H CH3  
Ethylone H O-CH2- O- H CH3 H CH2CH3  
Butylone H O-CH2- O- H CH2CH3 H CH3  
Pentylone H O-CH2- O- H CH2CH2CH3 H CH3  
N-ethyl-nor-pentylone H O-CH2- O- H CH2CH2CH3 H CH2CH3  
MDPV H O-CH2- O- H CH2CH2CH3 CH2CH2- CH2CH2-  
MDPHP H O-CH2- O- H CH2CH2CH2CH3 CH2CH2- CH2CH2-  

See also

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References

 

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