Substituted cathinone

Cathinone

Substituted cathinones are derivatives of cathinone, which includes some stimulants and entactogens. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat which is used as a recreational drug

Legality

On 2nd April 2010, the ACMD 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 of mephedrone, a common member of the family. This ban covers compounds with the following general structure, with 28 compounds specifically named.

"Any compound (not being bupropion or a substance for the time being specified in paragraph 2.2) structurally derived from 2-amino-1-phenyl-1-propanone by modification in any of the following ways, that is to say,

(i) by substitution in the phenyl ring to any extent with alkyl, alkoxy, alkylenedioxy, haloalkyl or halide substituents, whether or not further substituted in the phenyl ring by one or more other univalent substituents;

(ii) by substitution at the 3-position with an alkyl substituent;

(iii) by substitution at the nitrogen atom with alkyl or dialkyl groups, or by inclusion of the nitrogen atom in a cyclic structure."

— ACMD, 2nd April 2010

This text was added as an amendment to the Misuse of Drugs Act 1971, to come into force on 16 April 2010.

• R₁ = hydrogen, or any combination of one or more alkyl, alkoxy, alkylenedioxy, haloalkyl or halide substituents
• R₂ = hydrogen or any alkyl group
• R₃ = hydrogen, any alkyl group, or incorporation in a cyclic structure
• R₄ = hydrogen, any alkyl group, or incorporation in a cyclic structure

Chemical derivatives

Compound	R1	R2	R3	R4
Cathinone	no substitution	hydrogen	hydrogen	hydrogen
Methcathinone	no substitution	hydrogen	hydrogen	methyl
Ethcathinone	no substitution	hydrogen	hydrogen	ethyl
Buphedrone	no substitution	methyl	hydrogen	methyl
Pentedrone	no substitution	ethyl	hydrogen	methyl
Dimethylcathinone	no substitution	hydrogen	methyl	methyl
Diethylpropion	no substitution	hydrogen	ethyl	ethyl
Bupropion	3-chloro	hydrogen	hydrogen	t-butyl
Mephedrone	4-methyl	hydrogen	hydrogen	methyl
3-MMC	3-methyl	hydrogen	hydrogen	methyl
4-EMC	4-ethyl	hydrogen	hydrogen	methyl
4-MEC	4-methyl	hydrogen	hydrogen	ethyl
N,N-DMMC	4-methyl	hydrogen	methyl	methyl
N,N-DEMC	4-methyl	hydrogen	ethyl	ethyl
3,4-DMMC	3,4-dimethyl	hydrogen	hydrogen	methyl
Methedrone	4-methoxy	hydrogen	hydrogen	methyl
2-FMC	2-fluoro	hydrogen	hydrogen	methyl
3-FMC	3-fluoro	hydrogen	hydrogen	methyl
Flephedrone	4-fluoro	hydrogen	hydrogen	methyl
Brephedrone	4-bromo	hydrogen	hydrogen	methyl
bk-MDA	3,4-methylenedioxy	hydrogen	hydrogen	hydrogen
Methylone	3,4-methylenedioxy	hydrogen	hydrogen	methyl
Ethylone	3,4-methylenedioxy	hydrogen	hydrogen	ethyl
bk-IMP	3,4-trimethylene	hydrogen	hydrogen	methyl
4-Fluorobuphedrone	4-fluoro	methyl	hydrogen	methyl
4-Methylbuphedrone	4-methyl	methyl	hydrogen	methyl
Butylone	3,4-methylenedioxy	methyl	hydrogen	methyl
Eutylone	3,4-methylenedioxy	methyl	hydrogen	ethyl
bk-DMBDB	3,4-methylenedioxy	methyl	methyl	methyl
5-Methylmethylone	3,4-methylenedioxy-5-methyl	hydrogen	hydrogen	methyl
2-Methylbutylone	2-methyl-3,4-methylenedioxy	methyl	hydrogen	methyl
5-Methylbutylone	3,4-methylenedioxy-5-methyl	methyl	hydrogen	methyl
Pentylone	3,4-methylenedioxy	ethyl	hydrogen	methyl
α-Phthalimidopropiophenone	no substitution	hydrogen	phthalimido
α-PPP	no substitution	hydrogen	pyrrolidinyl
α-PBP	no substitution	methyl	pyrrolidinyl
4-Et-α-PBP	4-ethyl	methyl	pyrrolidinyl
4-MeO-α-PBP	4-methoxy	methyl	pyrrolidinyl
α-PVP	no substitution	ethyl	pyrrolidinyl
MPPP	4-methyl	hydrogen	pyrrolidinyl
MOPPP	4-methoxy	hydrogen	pyrrolidinyl
MPBP	4-methyl	methyl	pyrrolidinyl
Pyrovalerone	4-methyl	ethyl	pyrrolidinyl
MPHP	4-methyl	n-propyl	pyrrolidinyl
MDPPP	3,4-methylenedioxy	hydrogen	pyrrolidinyl
MDPBP	3,4-methylenedioxy	methyl	pyrrolidinyl
MDPV	3,4-methylenedioxy	ethyl	pyrrolidinyl
Naphyrone	β-naphthyl instead of phenyl	ethyl	pyrrolidinyl
bk-Methamthetamine	thiophen-2-yl instead of phenyl	hydrogen	hydrogen	methyl
α-PVT	thiophen-2-yl instead of phenyl	ethyl	pyrrolidinyl

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 was however 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 analogues

“Any compound structurally derived from 2–aminopropan–1–one by substitution at

the 1-position with any monocyclic, or fused-polycyclic ring system (not being a phenyl ring or alkylenedioxyphenyl ring system), whether or not the compound is further modified in any of the following ways, that is to say—

(i) by substitution in the ring system 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;

(ii) by substitution at the 3–position with an alkyl substituent;

(iii) by substitution at the 2-amino nitrogen atom with alkyl or dialkyl groups, or

by inclusion of the 2-amino nitrogen atom in a cyclic structure.”

— Home Office, 13th July 2010.

• 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
• R₁ = hydrogen or any alkyl group
• R₂ = hydrogen, any alkyl group, or incorporation in a cyclic structure
• R₃ = hydrogen, any alkyl group, or incorporation in a cyclic structure

See also

• Markush structure
• Substituted phenethylamines
• Substituted amphetamines
• Substituted methylenedioxyphenethylamines