1976-45-0

Usage

InChI:InChI=1/C20H23NO3/c22-15-5-3-12-9-14-13-4-6-16(23)19-20(13,17(12)18(15)24-19)7-8-21(14)10-11-1-2-11/h3-6,11,13-14,16,19,22-23H,1-2,7-10H2/t13-,14+,16-,19-,20-/m0/s1

Upstream product

• 4023-34-1 cyclopropanecarboxylic acid chloride 
• 20382-78-9 17-cyclopropanecarbonyl-3,6α-bis-cyclopropanecarbonyloxy-4,5α-epoxy-morphin-7-ene 
• 77794-51-5 17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-3-methoxymorphinan-6α-ol 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 91265-72-4 3-<(vinyloxy)carbonyl>normorphine hydrobromide 
• 5911-08-0 chloro(cyclopropyl)methane 
• 466-97-7 normorphine 
• 467-15-2 norcodeine 
• 103651-67-8 17-cyclopropanecarbonyl-6α-cyclopropanecarbonyloxy-4,5α-epoxy-3-methoxy-morphin-7-ene 
• 100323-42-0 17-cyclopropanecarbonyl-4,5α-epoxy-3-methoxy-morphin-7-en-6α-ol 
• 57-27-2 MORPHIN 
• 54260-60-5 2,2,2-trichloroethoxycarbonylnormorphine 
• 91265-71-3 3,17-bis<(vinyloxy)carbonyl>normorphine 
• 81815-58-9 3-O,N-dicyclopropylcarbonylnormorphine 

Downstream Products

• 129200-07-3 (-)-3-Acetyl-6β-(acetylthio)-N-(cyclopropylmethyl)normorphine 
• 91265-68-8 17-(cyclopropylmethyl)normorphinone 

Relevant academic research and scientific papers

Activities of morphinone and N-(cyclopropylmethyl)normorphinone at opioid receptors

Morphinone (3) and N-(cyclopropylmethyl)normorphinone (4) were synthesized and tested on electrically stimulated smooth muscle preparations (guinea pig ileum and mouse vas deferens) and in mice. Compound 3 behaved as an agonist and 4 as an antagonist in vitro and in vivo. No pronounced nonequilibrium agonist or antagonist activity was observed with either compound.

Synthesis and pharmacological activity of sulfate conjugates at 6-position of N-substituted normorphine derivatives

Three pairs of N-substituted normorphine derivatives and the sulfate conjugates at the 6-position were tested for the analgesic and antagonistic activities and the development of physical dependence in mice. The compounds examined were nalorphine, nalorphine-6-sulfate (N-6-S), N-cyclopropylmethylnormorphine (CPN), N-cyclopropylmethylnormorphine-6-sulfate (C-6-S), N-dimethylallylnormorphine (DMN) and N-dimethylallylnormorphine-6-sulfate (D-6-S). The latter two pairs were newly synthesized. The analgesic activity of C-6-S and D-6-S was equipotent to that of CPN and DMN by the acetic acid writhing test on the s.c. injection, and the activity of N-6-S was about 2 times more potent than that of nalorphine. The antagonistic activity of N-6-S, C-6-S and D-6-S to morphine analgesia was higher than that of the parent compounds by the tail pinch test on i.c.v. injection. A withdrawal sign was seen in mice treated chronically with CPN, C-6-S and N-6-S by challenge with naloxone, whereas the mice treated with DMN, D-6-S and nalorphine showed no such sign. The effect of sulfation at the 6-position on the development of physical dependence was not well associated with the effect on agonistic and antagonistic activities.

Diastereoisomeric quaternary morphinium salts: Synthesis, stereochemistry and analgesic properties

Diastereoisomeric quaternary morphinium salts were prepared by alkylation of morphine with alkyl halides or by alkylation of N-alkylnormorphines with methyl iodide. Nitrogen configuration of diastereoisomeric pairs was assigned by means of 1H NMR chemical shifts of corresponding N-methyl protons. These compounds were evaluated for analgesic activity by the guinea pig ileum assay and by the hot-plate test after icv administration in mice. The correlation between N-substituent orientation and narcotic agonist/antagonist activity is discussed.