259869-43-7Relevant academic research and scientific papers
3-(1',1'-Dimethylbutyl)-1-deoxy-Δ8-THC and related compounds: Synthesis of selective ligands for the CB2 receptor
Huffman, John W.,Liddle, John,Yu, Shu,Aung, Mie Mie,Abood, Mary E.,Wiley, Jenny L.,Martin, Billy R.
, p. 2905 - 2914 (1999)
The synthesis and pharmacology of 15 1-deoxy-Δ8-THC analogues, several of which have high affinity for the CB2 receptor, are described. The deoxy cannabinoids include 1-deoxy-11-hydroxy-Δ8-THC (5), 1-deoxy-Δ8-THC (6), 1-deoxy-3-butyl-Δ8-THC (7), 1-deoxy-3-hexyl-Δ8-THC (8) and a series of 3-(1',1'-dimethylalkyl)-1-deoxy-Δ8-THC analogues (2, n=0-4, 6, 7, where n=the number of carbon atoms in the side chain-2). Three derivatives (17-19Scheme 3(a) (C6H5)3PCH3+ Br-, n-BuLi/THF, 65°C; (b) LiAlH4/THF, 25°C; (c) KBH(sec-Bu)3/THF, -78 to 25°C then H2O2/NaOH.) of deoxynabilone (16) were also prepared. The affinities of each compound for the CB1 and CB2 receptors were determined employing previously described procedures. Five of the 3-(1',1'-dimethylalkyl)-1-deoxy-Δ8-THC analogues (2, n=1-5) have high affinity (K(i)=2 receptor. Four of them (2, n=1-4) also have little affinity for the CB1 receptor (K(i)=>295nM). 3-(1',1'-Dimethylbutyl)-1-deoxy-Δ8-THC (2, n=2) has very high affinity for the CB2 receptor (K(i)=3.4±1.0nM) and little affinity for the CB1 receptor (K(i)=677±132nM). Copyright (C) 1999 Elsevier Science Ltd.
