RTI uses cookies to offer you the best experience online. By clicking “accept” on this website, you opt in and you agree to the use of cookies. If you would like to know more about how RTI uses cookies and how to manage them please view our Privacy Policy here. You can “opt out” or change your mind by visiting: http://optout.aboutads.info/. Click “accept” to agree.
Synthesis and pharmacology of a hybrid cannabinoid
Huffman, JW., Lu, JZ., Dai, D., Kitaygorodskiy, A., Wiley, J., & Martin, BR. (2000). Synthesis and pharmacology of a hybrid cannabinoid. Bioorganic and Medicinal Chemistry, 8(2), 439-447.
A pentacyclic hybrid cannabinoid (4) has been synthesized, which combines structural elements of traditional cannabinoids and cannabmimetic indoles. Cannabinoid 4 contains a 1-pentylindole structure fused to the 2,3-positions of the partially reduced hydroxydibenzopyran system of THC. The successful approach to 4 employed 9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole (17) as the starting material. Dehydrogenation to carbazole 18, followed by demethylation and condensation with trans-p-menthadienol gave N-benzoyl hybrid cannabinoid 22, N-alkylation of which afforded target cannabinoid 4. The hybrid cannabinoid had affinity for the CB1 receptor approximately equal to that of Delta(8)-THC (K-i=19.3+/-3 nM), and shows comparable potency in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved