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Nalorphine

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Nalorphine
File: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
Identifiers
62-67-9 7pxY
V03AB02
PubChem CID 5284595
IUPHAR ligand 1629
ChemSpider 4447643 7pxY
UNII U59WB2WRY2 7pxN
ChEMBL CHEMBL415284 7pxN
Synonyms (−)−(5R,6S)-9α-allyl- 4,5-epoxymorphin- 7-en- 3,6-diol
Chemical data
Formula C19H21NO3
311.375 g/mol
 14pxN (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

File:Nalorphine synthesis.png
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. doi:10.1021/ja01256a036.  edit


Template:Opioidergics


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