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Ultrapure ajulemic acid has improved CB2 selectivity with reduced CB1 activity.

Mark A Tepper¹, Robert B Zurier¹, Sumner H Burstein²

¹JB Therapeutics Inc. (now named Corbus Pharmaceuticals, Inc.), One Kendall Square, Bldg 200, Cambridge, MA 02139, United States.

Bioorganic & Medicinal Chemistry

|May 27, 2014

Summary

Highly purified ajulemic acid (JBT-101) shows significantly weaker CB1 receptor binding than earlier preparations, suggesting a broader therapeutic index. This cannabinoid analog may offer therapeutic benefits without psychotropic effects.

Keywords:

Ajulemic acid Cannabinoid receptors Synthesis

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Area of Science:

Pharmacology
Medicinal Chemistry

Background:

Ajulemic acid, a synthetic cannabinoid analog, was developed to avoid psychotropic effects.
Previous studies reported conflicting findings regarding its adverse effects and therapeutic index.

Purpose of the Study:

To resolve discrepancies in ajulemic acid's adverse effect profile.
To compare cannabinoid receptor binding affinities of highly purified ajulemic acid with other preparations.

Main Methods:

Synthesized highly purified ajulemic acid (JBT-101) using a novel method.
Assessed cannabinoid receptor 1 (CB1) and CB2 binding affinities.
Evaluated functional responses including catalepsy and hypothermia.

Main Results:

CB2 binding affinities were consistent across all ajulemic acid samples.
CB1 binding affinities varied significantly, with JBT-101 exhibiting the weakest affinity.
The CB1/CB2 affinity ratio differed by 65-fold between JBT-101 and the original HU-239 preparation.
Functional assays confirmed reduced CB1 activity for JBT-101.

Conclusions:

The therapeutic index of ajulemic acid requires reevaluation based on the properties of highly purified JBT-101.
This purified form demonstrates a potentially improved safety profile compared to earlier ajulemic acid preparations.