Ajulemic Acid

Title: Ajulemic Acid
CAS Registry Number: 137945-48-3
CAS Name: (6aR,10aR)-3-(1,1-Dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9-carboxylic acid
Additional Names: 1¢,1¢-dimethylheptyl-D8-tetrahydrocannabinol-11-oic acid; (3R,4R)-D6-THC-DMH-7-oic acid
Manufacturers' Codes: CT-3; IP-751
Molecular Formula: C25H36O4
Molecular Weight: 400.55
Percent Composition: C 74.96%, H 9.06%, O 15.98%
Literature References: Cannabinoid receptor agonist; synthetic, nonpsychoactive derivative of D9-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 PPARg 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 Journal 7, E143-E148 (2005); J. L. Wiley, IDrugs 8, 1002-1011 (2005).
Properties: Crystals from acetonitrile, mp 112-114° (sintering). [a]D -275° (c = 3.8 in chloroform). Sol in most organic solvents. Practically insol in hexane.
Melting point: mp 112-114° (sintering)
Optical Rotation: [a]D -275° (c = 3.8 in chloroform)
Derivative Type: Acetate
Molecular Formula: C25H36O4.C2H2O
Molecular Weight: 442.59
Percent Composition: C 73.27%, H 8.65%, O 18.07%
Properties: Crystals from pentane, mp 120-122°. [a]D -265° (c = 9.0 in chloroform).
Melting point: mp 120-122°
Optical Rotation: [a]D -265° (c = 9.0 in chloroform)
Therap-Cat: Anti-inflammatory.
Keywords: Anti-inflammatory (Nonsteroidal).
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