Nalorphine

Nalorphine

Nalorphine
Systematic (IUPAC) name
(5α,6α)-17-allyl- 7,8-didehydro- 4,5-epoxymorphinan- 3,6-diol
Clinical data
AHFS/Drugs.com
Legal status
Identifiers
CAS number  YesY
ATC code V03
PubChem
IUPHAR ligand
ChemSpider  YesY
UNII  N
ChEMBL  N
Synonyms (−)−(5R,6S)-9α-allyl- 4,5-epoxymorphin- 7-en- 3,6-diol
Chemical data
Formula C19H21NO3 
Mol. mass 311.375 g/mol
 N   

Nalorphine (INN; Lethidrone, Nalline), also known as N-allyl-normorphine, is a mixed opioid agonist-antagonist. It acts at two opioid receptors, at the mu receptor it has antagonistic effects and at the kappa receptors it exerts high-efficacy agonistic characteristics. It is used to reverse opioid overdose and (starting in the 1950s) in a challenge test to determine opioid dependence.[1]

Synthesis

Nalorphine synthesis:[2]

More recently, it has become much more commonplace to use ethyl chloroformate instead of cyanogen bromide for the Von Braun degradation demethylation step. See for example the list of phenyltropanes or the synthesis of paroxetine for further examples of this.

See also

References

  1. ^ "Medicine: Drug Detector", Time, Dec. 24, 1956
  2. ^ Weijlard, J.; Erickson, A. E. (1942). "N-Allylnormorphine". Journal of the American Chemical Society 64 (4): 869.