1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Delta(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor.

Article Details

Citation

Copy to clipboard

Huffman JW, Hepburn SA, Lyutenko N, Thompson AL, Wiley JL, Selley DE, Martin BR

1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Delta(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor.

Bioorg Med Chem. 2010 Nov 15;18(22):7809-15. doi: 10.1016/j.bmc.2010.09.061. Epub 2010 Sep 29.

PubMed ID

20943404 [ View in PubMed

]

Abstract

Delta(8)-Tetrahydrocannabinol (26), 3-(1',1'-dimethylbutyl)- (12), 3-(1',1'-dimethylpentyl)- (13), 3-(1',1'-dimethylhexyl)- (14) and 3-(1',1'-dimethylheptyl)-Delta(8)-tetrahydrocannabinol (15) have been converted into the corresponding 1-bromo-1-deoxy-Delta(8)-tetrahydrocannabinols (25, 8-11). This was accomplished using a protocol developed in our laboratory in which the trifluoromethanesulfonate of a phenol undergoes palladium mediated coupling with pinacolborane. Reaction of this dioxaborolane with aqueous-methanolic copper(II) bromide provides the aryl bromide. The affinities of these bromo cannabinoids for the cannabinoid CB(1) and CB(2) receptors were determined. All of these compounds showed selectivity for the CB(2) receptor and one of them, 1-bromo-1-deoxy-3-(1',1'-dimethylhexyl)-Delta(8)-tetrahydrocannabinol (10), exhibits 52-fold selectivity for this receptor with good (28nM) affinity.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Dronabinol	Cannabinoid receptor 2	Ki (nM)	36	N/A	N/A	Details