198. Ajulemic Acid

Nomenclature

CAS number: 137945-48-3
(6aR,10aR)-3-(1,1-Dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9-carboxylic acid; 1′,1′-dimethylheptyl-Δ8-tetrahydrocannabinol-11-oic acid; (3R,4R)-Δ6-THC-DMH-7-oic acid; CT-3; IP-751.
C25H36O4; mol wt 400.55.
C 74.96%, H 9.06%, O 15.98%.

Description and references

Cannabinoid receptor agonist; synthetic, nonpsychoactive derivative of Δ9-tetrahydrocannabinol, q.v. Prepn: S. H. Burstein et al., J. Med. Chem. 35, 3135 (1992); S. H. Burstein, R. Mechoulam, WO 9401429; eidem, US 5338753 (both 1994). GC-MS determn in plasma: C. Batista et al., J. Chromatogr. B 820, 77 (2005). Binding to CB-receptors: M.-H. Rhee et al., J. Med. Chem. 40, 3228 (1997); to PPARγ receptor: J. Liu et al., Mol. Pharmacol. 63, 983 (2003). Clinical evaluation in chronic neuropathic pain: M. Karst et al., J. Am. Med. Assoc. 290, 1757 (2003). Reviews of development and pharmacology: S. Burstein et al., Life Sci. 75, 1513-1522 (2004); idem, AAPS J. 7, E143-E148 (2005); J. L. Wiley, IDrugs 8, 1002-1011 (2005).

Chemical structure

Properties

Crystals from acetonitrile, mp 112-114° (sintering). [α]D 275° (c = 3.8 in chloroform). Sol in most organic solvents. Practically insol in hexane.

Derivative

Acetate.
C25H36O4.C2H2O; mol wt 442.59.
C 73.27%, H 8.65%, O 18.07%.

Properties

Crystals from pentane, mp 120-122°. [α]D 265° (c = 9.0 in chloroform).

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal)