AM-1235 (1-(5-fluoropentyl)-3-(naphthalen-1-oyl)-6-nitroindole) is a drug that acts as a potent and reasonably selective

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

for the cannabinoid receptor CB₁.

Pharmacology

Pharmacodynamics

AM-1235 is a cannabinoid receptor

with K_i of 1.5 nM at CB₁ compared to 20.4 nM at CB₂. While the 6-nitro substitution on the

indole Indole is an organic compound with the formula . Indole is classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are derivatives of indole ...

ring reduces affinity for both CB₁ and CB₂ relative to the unsubstituted parent compound AM-2201, CB₂ affinity is reduced much more, resulting in a CB₁ selectivity of around 13 times. This is in contrast to other related compounds such as AM-1221 where a 6-nitro substitution instead confers significant selectivity for CB₂.

Pharmacokinetics

AM-1235

metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

differs only slightly from that of

JWH-018 JWH-018 (1-pentyl-3-(1-naphthoyl)indole, NA-PIMO or AM-678) is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2. It produces effe ...

. AM-1235 ''N''- dealkylation produces fluoropentane instead of

pentane Pentane is an organic compound with the chemical formula, formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomerism, structural isomers, or to a mixture of them: in the IUPAC nomenclature, h ...

(or plain

alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in whi ...

s in general). It has been speculated that the fluoropentane might function as an alkylating agent or is further metabolized into toxic fluoroacetic acid. This is not true since fluoroalkanes do not act as alkylating agents under normal conditions and uneven fluoroalkane chains metabolize into substantially less toxic fluoropropanoic acid.

Legal status

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as AM-1235 are

Schedule I Controlled Substance The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United State ...

References

{{Cannabinoids Designer drugs Naphthoylindoles Organofluorides AM cannabinoids Nitroarenes CB1 receptor agonists CB2 receptor agonists

Pharmacology

Pharmacodynamics

Pharmacokinetics

Legal status

See also

References