3792-68-5

Usage

Uses

Used in Veterinary Medicine:
Norbutorphanol is utilized as a pain reliever in veterinary applications, specifically for horses. It is particularly effective in managing pain due to its strong analgesic properties.
Used in Human Medical Research:
While not yet a standard treatment, norbutorphanol has been investigated for its potential role in treating addiction and withdrawal symptoms in humans. Its mechanism of action on opioid receptors suggests it may have therapeutic benefits in these areas, although further research is necessary to fully understand its potential and limitations.
Used in Clinical Settings with Caution:
Due to its potential for abuse and dependence, norbutorphanol should be used with caution in clinical settings. Careful consideration of the risks and benefits is essential when prescribing this medication to ensure patient safety and minimize the potential for misuse.

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 academic research and scientific papers

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.

Process for the preparation of 14-hydroxymorphinans

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-cyclopropylmethylmorphinan has been found to possess potent agonist-antagonist activity. A new and more efficient total synthesis for the preparation of these compounds is described herein, which improvement comprises using a Schiff base of 4a-(2-aminoethyl)-1,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene to produce 3-methoxy-9-bromo-norhasubanan hydrobromide in substantially improved yields through the intermediate of the formula SPC1

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.