Monday, December 30, 2013

Legislation View - How do we control substituted cathinones in the USA?

As we all know by now, substituted cathinones have been used in products available in smoke shops, gas stations and on the Internet for many years – the research chemical itself can be purchased over the Internet as well. Many of these substances have enactogenic and/or stimulant properties. On the flip-side, we simply do not know the pharmacological properties of many of these substances. Chemicals familiar to the layperson through media stories may be MDPV or Mephedrone.  But these are just two of a humongous number of substituted cathinones in existence. Now, ultimately, when substances such as these become prevalent in society, the various forms of government at the state and Federal levels decide they need to be controlled or banned.

So, how do state governments legislatively control substituted cathinones in the USA? Actually, it is quite easy to do with simple understanding of the general chemical structures of these substances.

Cue a minor amount of chemistry...
Substituted cathinones share the same overall chemical structure, which contain a phenethylamine core structure, an alpha carbon alkyl moiety, and a beta carbon ketone moiety. Specific substitutions can be made at any of the notated sites (R1-R4).

R1 can exist as hydrogen or combination of various alkyl, alkoxy, alkylenedioxy, haloalkyl, or halide moieties.
R2 can exist as hydrogen or any alkyl group.
R3 and R4 can exist as hydrogen, an alkyl moeity, or cyclic structure

Now consulting many of the state laws on this matter, one finds the following:
Any compound, except bupropion or a compound listed under a different schedule, structurally derived from 2-aminopropan-1-one by substitution at the 1-position with either phenyl, naphthyl, or thiophene ring systems, whether or not the compound is further modified:
(A) by substitution in the ring system to any extent with alkyl, alkylenedioxy, alkoxy, haloalkyl, hydroxyl, or halide substituents, whether or not further substituted in the ring system by one or more other univalent substituents;
(B) by substitution at the 3-position with an alkyl substituent
(C) by substitution at the 2-amino nitrogen atom with alkyl, dialkyl, benzyl, or methoxybenzyl groups; or
(D) by inclusion of the 2-amino nitrogen atom in a cyclic structure.
This exact wording or a form of it is used to ban the general class of cathinones in many states, including: Alaska, Arkansas, Colorado, Hawaii, Idaho, Indiana, Iowa, Kansas, Kentucky, Michigan, Minnesota, Nebraska, North Carolina, Ohio, South Carolina, South Dakota, and Tennessee
From memory (and this list isn’t exhaustive as I’m only doing this from recollection and not a reference book), this wording effectively controls the following compounds (and positional isomers):
Alpha-PBP, Alpha-PPP, Alpha-PVP, Benzedrone, Brephedrone, Buphedrone, Butylone, Chlorobuphedrone, Dibutylone, Diethylmethcathinone, Dimethylmethcathinone, Ethedrone, Ethylone, Ethylmethcathinone, Fluorobuphedrone, Fluoroethcathinone, Fluoromethcathinone, MDPBP, MDPPP, MDPV, Mephedrone, Methedrone, Methylone, Methylethcathinone, Naphyrone, N-ethylbuphedrone, Pentedrone, Pentylone.

Bupropion and Diethylpropion (Schedule IV) also fall under this class of drugs, but are typically excepted in the law or scheduled elsewhere.
If you’re goal is to control as many substituted cathinones in one giant swoop of  legislation, then this is a good way to accomplish that goal.  I believe more state governments will use this type of language in future legislation controlling these substances.

Could you do this with synthetic cannabinoids? No, not really.  But, we'll get into that another time.



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