1-methoxy-, 1-deoxy-11-hydroxy- and 11-Hydroxy-1-methoxy-Delta(8)-tetrahydrocannabinols: New selective ligands for the CB2 receptor
Huffman, J. W., Bushell, S. M., Miller, J. R. A., Wiley, J., & Martin, B. R. (2002). 1-methoxy-, 1-deoxy-11-hydroxy- and 11-Hydroxy-1-methoxy-Delta(8)-tetrahydrocannabinols: New selective ligands for the CB2 receptor. Bioorganic and Medicinal Chemistry, 10(12), 4119-4129.
Three series of new cannabinoids were prepared and their affinities for the CB, and CB, cannabinoid receptors were determined. These are the 1-methoxy-3-(1',1'-dimethylalkyl)-, 1-deoxy-11-hydroxy-3-(1',1'-dimethylalkyl)- and 11-hydroxy-1-methoxy-3-(1',1'-dimethylalkyl)-Delta(8)-tetrahydrocannabin ols. which contain alkyl chains from dimethylethyl to dimethylheptyl appended to C-3 of the cannabinoid. All of these compounds have greater affinity for the CB, receptor than for the CB, receptor. however only 1-methoxy-3-(1',1'-dimethylhexyl)-Delta(8)-THC (JWH-229, 6e) has effectively no affinity for the CB, receptor (K-i = 3134+/-110 nM) and high affinity for CB2 (K-i = 18 2 nM). (C) 2002 Elsevier Science Ltd. All rights reserved