Nalorphine

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Nalorphine
Nalorphine.svg
Systematic (IUPAC) name
(5α,6α)-17-allyl- 7,8-didehydro- 4,5-epoxymorphinan- 3,6-diol
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
Identifiers
CAS number 62-67-9 YesY
ATC code V03AB02
PubChem CID 5284595
IUPHAR ligand 1629
ChemSpider 4447643 YesY
UNII U59WB2WRY2 N
ChEMBL CHEMBL415284 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 (what is this?)  (verify)

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[edit]

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[edit]

References[edit]

  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. doi:10.1021/ja01256a036.  edit