Azidomorphine

Azidomorphine[1] is an opiate analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.[2]

Azidomorphine
Clinical data
Other namesAzidomorphine
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.041.211
Chemical and physical data
FormulaC17H20N4O2
Molar mass312.373 g·mol−1
3D model (JSmol)
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Azidomorphine binds with high affinity to the mu opioid receptor,[3] and is around 40x more potent than morphine in vivo. It has similar effects to morphine, including analgesia, sedation, and respiratory depression. However, its addiction liability has been found to be slightly lower than that of morphine in animal studies.[4][5]

References

  1. GB 1396663, "Analgesic Compositions"
  2. Knoll J, Fürst S, Kelemen K (December 1973). "The pharmacology of azidomorphine and azidocodeine". The Journal of Pharmacy and Pharmacology. 25 (12): 929–39. doi:10.1111/j.2042-7158.1973.tb09982.x. PMID 4150295.
  3. Horváth K, Wollemann M (November 1986). "Azidomorphine is an agonist of high-affinity opioid receptor binding sites". Neurochemical Research. 11 (11): 1565–9. doi:10.1007/bf00965775. PMID 2825053.
  4. Knoll J (1979). "Azidomorphines: a new family of potent analgesics with low dependence capacity". Progress in Neuro-Psychopharmacology. 3 (1–3): 95–108. doi:10.1016/0364-7722(79)90074-2. PMID 45567.
  5. Hill RC, Roemer D, Buescher H (June 1977). "Investigations of the analgesic and morphine-like properties of azidomorphine". The Journal of Pharmacology and Experimental Therapeutics. 201 (3): 580–6. PMID 405472.
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