3792-68-5

Basic information

• Product Name: norbutorphanol
• Synonyms: norbutorphanol
• CAS NO: 3792-68-5
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.34344
• Mol File: 3792-68-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 473.7°Cat760mmHg
• Flash Point: 182.2°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 8.86E-10mmHg at 25°C
• Refractive Index: 1.653
• PKA: 10.07±0.40(Predicted)
• CAS DataBase Reference: norbutorphanol(CAS DataBase Reference)
• NIST Chemistry Reference: norbutorphanol(3792-68-5)
• EPA Substance Registry System: norbutorphanol(3792-68-5)

Safety Data

• Hazardous Substances Data: 3792-68-5(Hazardous Substances Data)

Usage

General Description

Norbutorphanol is a synthetic opioid analgesic with potent analgesic effects and moderate sedative properties. It is chemically related to the opioid antagonist naloxone and the opioid agonist oxymorphone. Norbutorphanol is used in veterinary medicine as a pain reliever, particularly in horses, and has also been investigated for its potential use in treating addiction and withdrawal symptoms in humans. Its mechanism of action involves binding to and activating opioid receptors in the central nervous system, leading to pain relief and sedation. However, it also has the potential for abuse and dependence, and should be used with caution in clinical settings.

InChI:InChI=1/C16H21NO2/c18-12-4-3-11-9-14-16(19)6-2-1-5-15(16,7-8-17-14)13(11)10-12/h3-4,10,14,17-19H,1-2,5-9H2/t14-,15+,16+/m0/s1

Relevant articles and documents

Process for the preparation of 14-hydroxymorphinan derivatives

N-substituted-14-hydroxy-3-substituted-morphinan derivatives have been found to possess potent narcotic agonist or antagonist activity. In particular, the compound 3,14-dihydroxy-N-cyclobutylmethylmorphinan has been found to possess potent agonist/antagonist activity. A new and novel total synthesis for the preparation of these compounds is described herein.

Oxilorphan and butorphanol. Potent narcotic antagonists and nonaddicting analgesics in the 3,14 dihydroxymorphinan series. Part V

A series of 3,14 dihydroxymorphinans 8 was synthesized via a method of (a) acylation of 3 methoxy Δ84 morphinan 4a (b) stereospecific epoxidation of the resultant amides to β epoxides 5 (c) simultaneous reduction of amide and epoxide functions and (d) demethylation of the resultant 3 methoxy 14 hydroxymorphinans 7. Alternatively deblocking of the amine function in 5b by hydrolysis followed by reduction of the resultant amino epoxide 5e afforded 14 hydroxy 3 methoxymorphinan 7e, which is readily alkylated and demethylated to give various 8. On a basis of interesting pharmacological profiles compounds l 8c (oxilorphan) and l 8d (butorphanol) were selected for clinical studies.