Related Experiment Video
Updated: Jun 8, 2026

Oromucosal as an Alternative Method for Administration of Cannabis Products in Rodents
Published on: August 22, 2025
1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2)
John W Huffman1, Seon A Hepburn, Nataliya Lyutenko
1Howard L. Hunter Laboratory, Clemson University, Clemson, SC 29634-0973, United States. huffman@clemson.edu
Abstract:
Δ(8)-Tetrahydrocannabinol (26), 3-(1',1'-dimethylbutyl)- (12), 3-(1',1'-dimethylpentyl)- (13), 3-(1',1'-dimethylhexyl)- (14) and 3-(1',1'-dimethylheptyl)-Δ(8)-tetrahydrocannabinol (15) have been converted into the corresponding 1-bromo-1-deoxy-Δ(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)-Δ(8)-tetrahydrocannabinol (10), exhibits 52-fold selectivity for this receptor with good (28nM) affinity.
More Related Videos
Related Concept Videos
Chemotherapy-Induced Nausea and Vomiting: Cannabinoids
Two synthetic agonists of THC,...
π Molecular Orbitals of the Allyl Cation and Anion
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
π Molecular Orbitals of 1,3-Butadiene
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

