111129-14-7

Basic information

• Product Name: (5alpha)-17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl acetate
• CAS NO: 111129-14-7
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.4376
• Mol File: 111129-14-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 573.2°C at 760 mmHg
• Flash Point: 300.5°C
• Density: 1.42g/cm³
• Vapor Pressure: 5.6E-14mmHg at 25°C
• Refractive Index: 1.664
• CAS DataBase Reference: (5alpha)-17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (5alpha)-17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl acetate(111129-14-7)
• EPA Substance Registry System: (5alpha)-17-(cyclopropylmethyl)-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl acetate(111129-14-7)

Safety Data

• Hazardous Substances Data: 111129-14-7(Hazardous Substances Data)

Upstream product

• 16590-41-3 Naltrexone 
• 108-24-7 acetic anhydride 
• 16676-29-2 naltrexone Hydrochloride 
• 75-36-5 acetyl chloride 

Relevant articles and documents

New opioid receptor antagonist: Naltrexone-14-O-sulfate synthesis and pharmacology

Opioid antagonists, naloxone and naltrexone have long been used in clinical practice and research. In addition to their low selectivity, they easily pass through the blood-brain barrier. Quaternization of the amine group in these molecules, (e.g. methylnaltrexone) results in negligible CNS penetration. In addition, zwitterionic compounds have been reported to have limited CNS access. The current study, for the first time gives report on the synthesis and the in vitro [competition binding, G-protein activation, isolated mouse vas deferens (MVD) and mouse colon assay] pharmacology of the zwitterionic compound, naltrexone-14-O-sulfate. Naltrexone, naloxone, and its 14-O-sulfate analogue were used as reference compounds. In competition binding assays, naltrexone-14-O-sulfate showed lower affinity for μ, δ or κ opioid receptor than the parent molecule, naltrexone. However, the μ/κ opioid receptor selectivity ratio significantly improved, indicating better selectivity. Similar tendency was observed for naloxone-14-O-sulfate when compared to naloxone. Naltrexone-14-O-sulfate failed to activate [35S]GTPγS-binding but inhibit the activation evoked by opioid agonists (DAMGO, Ile5,6deltorphin II and U69593), similarly to the reference compounds. Schild plot constructed in MVD revealed that naltrexone-14-O-sulfate acts as a competitive antagonist. In mouse colon, naltrexone-14-O-sulfate antagonized the inhibitory effect of morphine with lower affinity compared to naltrexone and higher affinity when compared to naloxone or naloxone-14-O-sulfate. In vivo (mouse tail-flick test), subcutaneously injected naltrexone-14-O-sulfate antagonized morphine's antinociception in a dose-dependent manner, indicating it's CNS penetration, which was unexpected from such zwitter ionic structure. Future studies are needed to evaluate it's pharmacokinetic profile.

CRYSTAL OF 6,7-UNSATURATED-7-CARBAMOYL MORPHINAN DERIVATIVE AND METHOD FOR PRODUCING THE SAME

Stable crystalline forms of a compound represented by the formula (IA): an acid addition salt, and/or a solvate thereof are provided by the present invention. Said crystalline forms are extremely useful as materials for preparing medicines. Novel processes for preparing 6,7-unsaturated-7-carbamoyl morphinan derivatives are also provided by the present invention.

Process for the Preparation of Quaternary N-Alkyl Morphinan Alkaloid Salts

An improved process for the N-alkylation of tertiary morphinan alkaloid bases to form the corresponding quaternary morphinan alkaloid derivatives.