Defining Cannabimimetic

Following up my previous post, I went into the proposed legislation and found the relevant section, which I reproduce here:

SEC. 1152. ADDITION OF SYNTHETIC DRUGS TO SCHEDULE I OF THE CONTROLLED SUBSTANCES ACT.

(a) Cannabimimetic Agents- Schedule I, as set forth in section 202(c) of the Controlled Substances Act (21 U.S.C. 812(c)) is amended by adding at the end the following:

‘(d)(1) Unless specifically exempted or unless listed in another schedule, any material, compound, mixture, or preparation which contains any quantity of cannabimimetic agents, or which contains their salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation.

‘(2) In paragraph (1):

‘(A) The term ‘cannabimimetic agents’ means any substance that is a cannabinoid receptor type 1 (CB1 receptor) agonist as demonstrated by binding studies and functional assays within any of the following structural classes:

‘(i) 2-(3-hydroxycyclohexyl)phenol with substitution at the 5-position of the phenolic ring by alkyl or alkenyl, whether or not substituted on the cyclohexyl ring to any extent.

‘(ii) 3-(1-naphthoyl)indole or 3-(1-naphthylmethane)indole by substitution at the nitrogen atom of the indole ring, whether or not further substituted on the indole ring to any extent, whether or not substituted on the naphthoyl or naphthyl ring to any extent.

‘(iii) 3-(1-naphthoyl)pyrrole by substitution at the nitrogen atom of the pyrrole ring, whether or not further substituted in the pyrrole ring to any extent, whether or not substituted on the naphthoyl ring to any extent.

‘(iv) 1-(1-naphthylmethylene)indene by substitution of the 3-position of the indene ring, whether or not further substituted in the indene ring to any extent, whether or not substituted on the naphthyl ring to any extent.

‘(v) 3-phenylacetylindole or 3-benzoylindole by substitution at the nitrogen atom of the indole ring, whether or not further substituted in the indole ring to any extent, whether or not substituted on the phenyl ring to any extent.

‘(B) Such term includes–

‘(i) 5-(1,1-dimethylheptyl)-2-[(1R,3S)-3-hydroxycyclohexyl]-phenol (CP-47,497);

‘(ii) 5-(1,1-dimethyloctyl)-2-[(1R,3S)-3-hydroxycyclohexyl]-phenol (cannabicyclohexanol or CP-47,497 C8-homolog);

‘(iii) 1-pentyl-3-(1-naphthoyl)indole (JWH-018 and AM678);

‘(iv) 1-butyl-3-(1-naphthoyl)indole (JWH-073);

‘(v) 1-hexyl-3-(1-naphthoyl)indole (JWH-019);

‘(vi) 1-[2-(4-morpholinyl)ethyl]-3-(1-naphthoyl)indole (JWH-200);

‘(vii) 1-pentyl-3-(2-methoxyphenylacetyl)indole (JWH-250);

‘(viii) 1-pentyl-3-[1-(4-methoxynaphthoyl)]indole (JWH-081);

‘(ix) 1-pentyl-3-(4-methyl-1-naphthoyl)indole (JWH-122);

‘(x) 1-pentyl-3-(4-chloro-1-naphthoyl)indole (JWH-398);

‘(xi) 1-(5-fluoropentyl)-3-(1-naphthoyl)indole (AM2201);

‘(xii) 1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole (AM694);

‘(xiii) 1-pentyl-3-[(4-methoxy)-benzoyl]indole (SR-19 and RCS-4);

‘(xiv) 1-cyclohexylethyl-3-(2-methoxyphenylacetyl)indole (SR-18 and RCS-8); and

‘(xv) 1-pentyl-3-(2-chlorophenylacetyl)indole (JWH-203).’.

(b) Other Drugs- Schedule I of section 202(c) of the Controlled Substances Act (21 U.S.C. 812(c)) is amended in subsection (c) by adding at the end the following:

‘(18) 4-methylmethcathinone (Mephedrone).

‘(19) 3,4-methylenedioxypyrovalerone (MDPV).

‘(20) 2-(2,5-Dimethoxy-4-ethylphenyl)ethanamine (2C-E).

‘(21) 2-(2,5-Dimethoxy-4-methylphenyl)ethanamine (2C-D).

‘(22) 2-(4-Chloro-2,5-dimethoxyphenyl)ethanamine (2C-C).

‘(23) 2-(4-Iodo-2,5-dimethoxyphenyl)ethanamine (2C-I).

‘(24) 2-[4-(Ethylthio)-2,5-dimethoxyphenyl]ethanamine (2C-T-2).

‘(25) 2-[4-(Isopropylthio)-2,5-dimethoxyphenyl]ethanamine (2C-T-4).

‘(26) 2-(2,5-Dimethoxyphenyl)ethanamine (2C-H).

‘(27) 2-(2,5-Dimethoxy-4-nitro-phenyl)ethanamine (2C-N).

‘(28) 2-(2,5-Dimethoxy-4-(n)-propylphenyl)ethanamine (2C-P).’.

SEC. 1153. TEMPORARY SCHEDULING TO AVOID IMMINENT HAZARDS TO PUBLIC SAFETY EXPANSION.

Section 201(h)(2) of the Controlled Substances Act (21 U.S.C. 811(h)(2)) is amended–

(1) by striking ‘one year’ and inserting ‘2 years’; and

(2) by striking ‘six months’ and inserting ‘1 year’.

My first impression is that it reads like a patent. That is likely the best angle to take on this, something broad enough to cover what might be made but narrow enough to avoid over-reaching and impinging upon unrelated research work.

It looks like they covered the basic structural motifs seen in CP-47,497 (along with some related compounds like HU-243) and JWH-018, along with some related JWH indoles. I was glad to see that they were quite careful with the wording on the indoles, so that clear derivatives of the CB agonists would be covered but not necessarily all indole chemistry. They included the pyrroles and indenes but no specific examples of those, which I thought a weakness of the statement. The broad number of examples in the indoles leads me to think they are basing it on examples found in incense and bath salt products. I will also applaud the inclusion of a specific phrase that includes the measured biological activity (in binding and functional assays), which is to me at least the most defining feature of a CB agonist.