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Bioorg Med Chem Lett. 2012 Feb 15;22(4):1619-24. doi: 10.1016/j.bmcl.2011.12.124. Epub 2012 Jan 4.

γ-Carbolines: a novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration.

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  • 1Department of Medicinal Chemistry, AstraZeneca R&D Montreal, Saint-Laurent, Quebec, Canada.


An oral, peripherally restricted CB1/CB2 agonist could provide an interesting approach to treat chronic pain by harnessing the analgesic properties of cannabinoids but without the well-known central side effects. γ-Carbolines are a novel class of potent mixed CB1/CB2 agonists characterized by attractive physicochemical properties including high aqueous solubility. Optimization of the series has led to the discovery of 29, which has oral activity in a rat inflammatory pain model and limited brain exposure at analgesic doses, consistent with a lower risk of CNS-mediated tolerability issues.

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