20736-10-1Relevant articles and documents
Analgesic and immunomodulatory effects of codeine and codeine 6-glucuronide
Srinivasan, Vinayak,Wielbo, Donna,Simpkins, James,Karlix, Janet,Sloan, Kenneth,Tebbett, Ian
, p. 296 - 300 (1996)
Purpose. The antinociceptive and immunosuppressive effects of codeine and codeine 6-glucuronide were determined in rats after intracerebroventricular administration. Methods. Codeine 6-glucuronide was synthesized using a modification of the Koenigs-Knorr reaction. A lipophilic intermediate formed during synthesis, methyl [codein-6-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosid] uronate, was also tested. Morphine was used as a positive control to compare antinociceptive potencies of these compounds. Results. All compounds tested produced significant analgesic responses, as assessed by the tail flick model. Additionally, codeine 6-glucuronide showed significantly less immunosuppressive effects than codeine in vitro. Conclusions. We conclude that codeine 6-glucuronide and related compounds may have clinical benefit in the treatment of pain in immune compromised patients.
Selective synthesis of both isomers of morphine 6-β-D-glucuronide and their analogs
Rukhman, Igor,Yudovich, Lev,Nisnevich, Gennadiy,Gutman, Arie L
, p. 1083 - 1092 (2007/10/03)
A stereoselective synthesis of both isomers of the pharmaceutically important morphine 6-β-D-glucuronide (M6G) and its analogs was developed. The method is based on the use of ZnBr2 for the key coupling reaction. It was shown that the α/β stere