20410-98-4

Usage

Chemical Properties

Pale Yellow Solid

Uses

A metabolite of Naltrexone.

InChI:InChI=1/C20H25NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,14-15,18,22-24H,1-2,5-10H2/t14-,15?,18?,19?,20?/m1/s1

Upstream product

• 16590-41-3 Naltrexone 
• 116388-85-3 (5α,6α)-17-(cyclopropylmethyl)-4,5-epoxy-3-methoxymorphinan-6,14-diol 
• 16676-29-2 naltrexone Hydrochloride 
• 67210-64-4 6α,14β-diacetoxy-4,5percenta-epoxy-3-methoxy-17-methyl-morphinan 
• 33522-95-1 noroxymorphone 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 124154-49-0 3-O-(tert-butyldimethylsilyl)-4,5α-epoxy-3,6α,14-trihydroxy-17-(cyclopropylmethyl)morphinan 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 58477-92-2 14-hydroxydihydronormorphine 
• 116388-83-1 C₂₂H₂₄N₂O₆ 
• 116499-16-2 beta-Noroxycodol 
• 142641-92-7 C₂₄H₂₇NO₈ 

Downstream Products

• 159465-54-0 17-(cyclopropylmethyl)-3-(benzyloxy)-4,5α-epoxy-6α,14-dihydroxymorphinan 
• 159465-61-9 17-(cyclopropylmethyl)-3-(triphenylmethoxy)-4,5α-epoxy-6α,14-dihydroxymorphinan 
• 159465-55-1 17-(cyclopropylmethyl)-3,6α-bis(benzyloxy)-4,5α-epoxy-14-hydroxymorphinan 
• 159465-59-5 17-(cyclopropylmethyl)-3-(benzyloxy)-6α-(1-naphthylmethoxy)-4,5α-epoxy-14-hydroxymorphinan 
• 159465-57-3 17-(cyclopropylmethyl)-3-(benzyloxy)-6α-(2-naphthylmethoxy)-4,5α-epoxy-14-hydroxymorphinan 
• 159465-56-2 17-(cyclopropylmethyl)-3-(benzyloxy)-6α-(4-biphenylylmethoxy)-4,5α-epoxy-14-hydroxymorphinan 
• 159465-60-8 17-(cyclopropylmethyl)-3-(triphenylmethoxy)-6α-(9-anthracylmethoxy)-4,5α-epoxy-14-hydroxymorphinan 

Relevant academic research and scientific papers

CONVENIENT PREPARATION OF N-SUBSTITUTED MORPHINAN-6-OLS FROM MORPHINAN-6-ONES

Described herein are methods of preparing 6-hydroxy N-alkyl morphinan-6-ols from morphinan-6-ones, as illustrated below: wherein the variables R1, R2, R3, R10, R11, R14, and are as defined herein and wherein the reactions occur in a one-pot procedure using a boron based reducing agent.

Application of SO3H silica gel to deprotection of silyl ethers

A newly developed SO3H silica gel cleaved the O-Si bonds in various aryl and alkyl silyl ethers to give the corresponding phenols and alcohols in good to excellent yield. The crude filtrates contained no silyl residues. The solid phase 29Si NMR analyses of the SO3H silica gel strongly suggested that the silyl residues were captured by silanol groups on the surface of the silica gel. The SO3H silica gel could be recycled at least ten times without any loss of activity. The disappearance of silyl residues in the crude filtrate was observed in even the 10th repetition. Our method provides an easily handled desilylation method that requires no further purification. Our method was also applicable to a selective desilylation reaction of a derivative 5 with different siloxy groups or desilylation of an alkaloid derivative 7.

PROCESS FOR REDUCING THE 6-KETO GROUP OF A MORPHINAN ALKALOID TO THE 6-HYDROXY GROUP BY HYDROGENATION

The present invention relates to a process for the reduction of a 6-keto group in a morphinan alkaloid to the corresponding 6-hydroxy group, comprising hydrogenating the 6-keto group using gaseous hydrogen in the presence of a heterogeneous catalyst and a solvent, to yield the 6-hydroxy morphinan alkaloid, wherein the reduction is carried out at a pH in the range of about 5 to about 7, and the 6-hydroxy morphinan alkaloid has an α:β ratio of > 85: 15.

PROCESS FOR MAKING MORPHINAN-6alpha-OLS

The present invention provides a process whereby morphinan-6-ones can be converted stereospecifically to the corresponding morphinan-6α-ols by catalytic hydrogenation under basic conditions.

IMPROVED PROCESS FOR THE PREPARATION OF 6-ALPHA-HYDROXY-N-ALKYLATED OPIATES

The present invention is directed to the conversion of a 6-keto morphinan to a 6-alpha-hydroxy morphinan in the presence of a ruthenium, rhodium, or iridium asymmetric catalyst and a hydrogen source.

Syntheses and receptor-binding studies of derivatives of the opioid antagonist naltrexone

Naltrexone (1), which is a member of the group of competitive opioid antagonists, shows a strong affinity for μ-receptors and its derivatives have been notable as novel receptor anatgonists. In this paper, the preparation of several naltrexone derivatives is described; these were used to investigate the role of the oxygenated functional groups in facilitating binding to a series of the opioid receptors. The derivatives showed affinity for opioid μ-receptors which was similar to that of naltrexone, but these compounds, which had masked hydroxyl functional groups, displayed a moderate activity. These results suggest that every oxygenated functional group in naltrexone (1) plays an important role in binding to the opioid receptor.

Morphine Alkaloids, Part 114 A. Stereohomogeneous Synthesis of N-Demethyl-N-Substituted-14-Hydroxydihydromorphines

A new route for the stereohomogeneous synthesis of N-demethyl-N-substituted-14-hydroxydihydromorphines 2a-f has been elaborated, involving O-demethylation of the novel dihydrocodeine derivatives 6a-f, obtained upon alkylation of the hitherto unknown N-demethyl-14-hydroxydihydrocodeine (5). Keywords. 6α,14β-Diacetoxy-4,5α-epoxy-3-methoxy-17-methyl-morphinan, N-demethylation of; 3,6α,14β-Triacetoxy-17-alkyl-4,5α-epoxymorphinan, N-demethylation of; 17-Alkyl-4,5α-epoxy-6α,14β-dihydroxy-3-methoxymorphinan, O-demethylation of; 4,5α-Epoxy-6α,14β-dihydroxy-3-methoxymorphinan, N-alkylation of.

Probes for Narcotic Receptor Mediated Phenomena. 18. Epimeric 6α- and 6β-Iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinans as Potential Ligands for Opioid Receptor Single Photon Emission Computed Tomography: Synthesis, Evaluation, and Radiochemistry of...

The epimeric 6β- and 6α-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinans (1, ioxy) and (2, epioxy), respectively, were each synthesized in five steps starting with naltrexone.The configuration of the 6-iodo group of 1 was unequivocally determined to be β-based on single crystal X-ray analysis of its precursor 3-acetoxy-6β-iodo-14-hydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan (10).Both 1 and 2 as well as their corresponding 3-O-acetates 10 and 11 were found to readily cross the blood-brain barrier and completely reverse the analgesic effects of a 10 mg/kg intraperitoneal dose of morphine sulfate as determined by the paw withdrawal latency test.Compounds 1 and 2 were found to bind with high affinity to μ, δ and κ receptors in vitro.In general, 1 and 2 exhibited higher affinity for μ and κ receptors than naltrexone while the 6β-iodo epimer 1 (ioxy) was more potent than its epimer 2.In a comparison of the 6β-halogen substituent on binding affinity across opioid receptor subtypes, it was generally found that I>Br>F.On the basis of the results of in vitro and in vivo testing, 1 was selected as a target for radioiodination and evaluation as a potential single photon emission computed tomography imaging agent for opioid receptors.Carrier-free -1 was synthesized in near quantitative yield by the sequence of reaction of excess 3-acetoxy-6α-oxy>-14-hydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan (8) with anhydrous Na125I in dry acetonitrile for 90 min at 76 deg C followed by deacetylation of the product with 1:1 aqueous ammonia/acetonitrile at 25 deg C.The potential of -1 as an in vivo imaging agent for opioid receptors is evaluated and discussed.

Process for the stereoselective reduction of 6- and 8-keto morphine and morphinan derivatives with formamidinesulfinic acid and compounds obtained thereby

Process for the stereoselective synthesis of 6β-and 8β- hydroxy epimers by the chemical reduction of 6- and 8-keto derivatives in the morphine and morphinan series utilizing alkaline formamidinesulficic acid. The 6β- and 8β-hydroxy derivatives obtained according to the invention evidence narcotic antagonist and/or agonist activity and are also useful in the chemical and pharmacological standardization of various morphine and codeine derivatives and metabolites.