Cannabinoids

Pharmacological Actions of Cannabinoids 19

Table 4.Kivalues of certain other ligands for the in vitro displacement of [^3 H]CP55940 or [^3 H]HU243afrom
CB 1 -andCB 2 -specific binding sites

Ligand CB 1 CB 2 Reference

Kivalue (nM) Kivalue (nM)

CB 1 -selective ligands in order of decreasing CB 1 /CB 2 selectivity

R-N-(1-methyl-2-hydroxyethyl)- 7.42b,c 1,952d Goutopoulos et al. 2001

2-R-methyl-arachidonamide

O-585 8.6b 324 b Showalter et al. 1996

O-689 5.7b 132 b Showalter et al. 1996

Ligands without any marked CB 1 or CB 2 selectivity

Ajulemic acid (CT-3) 32.3a,c 170.5a Rhee et al. 1997

11-OH-cannabinol-DMH 0.1a,c 0.2a Rhee et al. 1997

3-(1′,1′-dimethyl-cyclohexyl)-∆^8 -THC 0.57 0.65 Krishnamurthy et al. 2003

11-OH-cannabinol 38 a,c 26.6a Rhee et al. 1997

∆^9 -THC-DMH 0.241a,c 0.199a Rhee et al. 1997

Cannabinol-DMH 2 a,c 1.5a Rhee et al. 1997

Cannabidiol 4,350 2,860 Showalter et al. 1996

> 10 a,c > 10 a,e Bisogno et al. 2001

11-OH-∆^8 -THC 25.8a,c 7.4a Rhee et al. 1997

1-Deoxy-∆^8 -THC-DMH 23 c 2.9 Huffman et al. 1996

3-(1′,1′-cyclopropyl-heptyl)-∆^8 -THC 0.44c 0.86d Papahatjis et al. 2002

O-1184 5.25 7.41 Ross et al. 1999b

cis(6aS, 10aS)-3-(1′,1′-DMH)- 1,990 >10,000 Showalter et al. 1996

11-hydroxy-∆^8 -THC (HU-211)

Abnormal-cannabidiol >10,000 >10,000 Showalter et al. 1996

CB 2 -selective ligands in order of increasing CB 1 /CB 2 selectivity

JWH-015 383 13.8 Showalter et al. 1996

1-Deoxy-11-hydroxy- 1.2c 0.032 Huffman et al. 1996

∆^8 -THC-DMH (JWH-051)

JTE-907 2,370 35.9 Iwamura et al. 2001

L-768242 1,917 12 Gallant et al. 1996

3-(1′ 1 ′-dimethylpropyl)- 2,290c 14 Huffman et al. 1999

1-deoxy-∆^8 -THC (JWH-139)

3-(1′ 1 ′-dimethylhexyl)- 3,134c 18 Huffman et al. 2002

1-methoxy-∆^8 -THC

1-Deoxy-∆^8 -THC >10,000c 32 Huffman et al. 1999

See Figs. 1, 4, 5, 7, 8, 9, 11 and 12 for the structures of some of the compounds listed in this table.
DMH, dimethylheptyl; ND, not determined; THC, tetrahydrocannabinol.
bWith phenylmethylsulphonyl fluoride (PMSF) in order to inhibit enzymic hydrolysis.
cBinding to rat cannabinoid receptors on transfected cells or on brain (CB 1 ) or spleen tissue (CB 2 ).
dBinding to mouse brain (CB 1 ) or spleen tissue (CB 2 ).
eSpecies unspecified. All other data from experiments with human cannabinoid receptors.

drolysis. Although insertion of this group into ACEA does markedly reduce the
susceptibility of this molecule to FAAH-mediated hydrolysis, it also decreases the
affinity of ACEA for CB 1 receptors by about 14-fold (Jarrahian et al. 2000).R-N-(1-