14696-23-2

Basic information

• Product Name: NorhydroMorphone
• Synonyms: (5α)-4,5-Epoxy-3-hydroxyMorphinan-6-one;4,5α-Epoxy-3-hydroxyMorphinan-6-one;N-DeMethylhydroMorphone;Nor HydroMorphone;NordihydroMorphone;NorhydroMorphone
• CAS NO: 14696-23-2
• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.31108
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Neurochemicals;Pharmaceuticals
• Mol File: 14696-23-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 305-306 °C
• Boiling Point: 496.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• PKA: 9.03±0.20(Predicted)
• CAS DataBase Reference: NorhydroMorphone(CAS DataBase Reference)
• NIST Chemistry Reference: NorhydroMorphone(14696-23-2)
• EPA Substance Registry System: NorhydroMorphone(14696-23-2)

Safety Data

• Hazardous Substances Data: 14696-23-2(Hazardous Substances Data)

Usage

Uses

Norhydromorphone is a novel metabolite of Hydromorphone (H714650).

Upstream product

• 466-99-9 hydromorphone 
• 58752-60-6 3-O-acetyldihydromorphine 
• 1421-28-9 Dihydromorphine hydrochloride 
• 71-68-1 hydromorphone hydrochloride 
• 33049-61-5 (-)-tetrahydrothebaine 
• 85618-66-2 (-)-4,5-epoxy-3-hydroxy-N-(2,2,2-trichloroethoxycarbonyl)morphinan-6-one 
• 466-97-7 normorphine 

Relevant articles and documents

Identification and synthesis of norhydromorphone, and determination of antinociceptive activities in the rat formalin test

The main objective of this paper is to report the identification and synthesis of norhydromorphone, a novel metabolite of hydromorphone, and its antinociceptive activities when tested in the formalin test as compared to other known analgesics. In addition, we are reporting for the first time the lack of antinociceptive activities of hydromorphone-3-glucuronide, dihydromorphine-3- glucuronide and dihydroisomorphine-3-glucuronide in the rat formalin test. Norhydromorphone was isolated and identified as a metabolite of hydromorphone in a cancer patient's urine. An authentic standard of norhydromorphone was synthesized. The identity of norhydromorphone in the urine sample was confirmed by comparing the LC retention time and MS ion fragmentation with the synthetic standard using a liquid chromatographic-mass spectrometric-mass spectrometric (LC-MS-MS) assay. Norhydromorphone was found to be a minor metabolite of hydromorphone in the urine. Additionally, the antinociceptive activities of norhydromorphone, hydromorphone, morphine, dihydromorphine, dihydroisomorphine, hydromorphone-3-glucuronide, dihydromorphine-3-glucuronide and dihydroisomorphine-3-glucuronide were determined in the rat formalin test following intraperitoneal (i.p.) administration. Only limited antinociception was observed and no significant increase in antinociception was detected at the three doses tested. The increased polarity of norhydromorphone as compared to hydromorphone due to the primary piperidine nitrogen may make it less favorable to cross the blood-brain-barrier (BBB), which may be partly responsible. In addition, lower intrinsic antinociceptive activity, which remains to be determined, could also contribute to the low antinociception. Our results also show that hydromorphone was five times as potent as morphine in the formalin test, while dihydromorphine and dihydroisomorphine were equipotent to and 36% as potent as morphine, respectively. Hydromorphone-3-glucuronide, dihydromorphine-3-glucuronide and dihydroisomorphine-3-glucuronide did not exhibit any antinociceptive effect at the doses tested. The results further underscore the importance of a free C3-OH to the analgesic effect of morphine alkaloids.

N-OXIDES OF 4,5-EPOXY-MORPHINANIUM ANALOGS

Novel N-oxides of 4,5-epoxy-morphinanIum analogs are disclosed. Pharmaceutical compositions containing the N-oxides of 4,5-epoxy-morphinanium analogs and methods of their pharmaceutical uses are also disclosed. The compounds disclosed are useful, inter alia, as modulators of opioid receptors.