118111-54-9

Usage

Biological Activity

Selective μ -opioid receptor antagonist (K i values are 5.4, 244.6 and 2187 nM for μ -, δ - and κ -opioid receptors respectively). Reduces levodopa-induced dyskinesia in the MPTP-lesioned primate model of Parkinson's disease.

InChI:InChI=1/C22H29NO3/c1-25-18-5-3-4-16-12-19-22(26-2)9-8-17(24)13-21(22,20(16)18)10-11-23(19)14-15-6-7-15/h3-5,15,19H,6-14H2,1-2H3/t19-,21-,22+/m0/s1

Upstream product

• 124919-20-6 17-(cyclopropylmethyl)-4-hydroxy-14β-methoxymorphinan-6-one 
• 138-24-9 phenyltrimethylammonium chloride 
• 124919-40-0 (-)-N-(cyclopropylmethyl)-4,5α-epoxy-14-methoxymorphinan-6-one 
• 16676-29-2 naltrexone Hydrochloride 
• 124919-39-7 (-)-4,5α-epoxy-14-methoxymorphinan-6-one hydrobromide 
• 118111-52-7 (-)-4,14-dimethoxy-N-<(2,2,2-trichloroethoxy)carbonyl>morphinan-6-one 
• 92055-59-9 (-)-4,14-dimethoxy-N-methylmorphinan-6-one 
• 155732-90-4 17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxy-3-[(1-phenyl-1H-tetrazol-5-yl)oxy]-morphinan-6-one 
• 155732-91-5 17-cyclopropylmethyl-6,7-didehydro-4,5α-epoxy-6,14-dimethoxymorphinian 
• 152659-61-5 (5R,9R,13S,14S)-17-(cyclopropylmethyl)-4,5-epoxy-14-hydroxymorphinan-6-one 
• 118111-53-8 (-)-4,14-dimethoxymorphinan-6-one 
• 5911-08-0 chloro(cyclopropyl)methane 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 14-alkoxymorphinans. 2. (-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one, a selective μ opioid receptor antagonist

(-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one (2) was synthesized with 4,14-dimethoxy-N-methyl-morphinan-6-one (1) as starting material. In vivo and in vitro experiments show 2 (cyprodime) to be a pure opioid receptor antagonist. Some of these tests (opioid receptor binding assays, guinea pig ileal longitudinal muscle preparation, rat and mouse vas deferens preparation, acetic acid writhing antagonism (test) indicate that 2 is a selective μ opioid receptor antagonist.

A NEW AND EFFICIENT SYNTHESIS OF THE μ-SELECTIVE OPIOID ANTAGONIST CYPRODIME

The μ-selective opioid antagonist cyprodime has been prepared in a six-step sequence starting from naltrexone.The 3-hydroxy group of naltrexone was removed via tetrazolyl ether (3) which was hydrogenated catalytically to give 17-cyclopropylmethyl-4,5α-epo

Synthesis and biological evaluation of 14-alkoxymorphinans. 3. Extensive study on cyprodime-related compounds

A series of cyprodime-related compounds (2, 4-12, and 26) has been synthesized and evaluated for opioid agonist and antagonist activity with the mouse vas deferens and guinea pig ileum preparations. None of the changes to cyprodime, including the introduc