Azidomorphine

Azidomorphine
Skeletal formula of azidomorphine
Space-filling model of the azidomorphine molecule
Clinical data
Other namesAzidomorphine
ATC code
  • none
Identifiers
IUPAC name
  • (6β)-Azido-4,5-α-epoxy-17-methyl morphinan-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.041.211
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Chemical and physical data
FormulaC17H20N4O2
Molar mass312.373 g·mol−1
3D model (JSmol)
SMILES
  • [N-]=[N+]=N\[C@H]4[C@@H]5Oc1c2c(ccc1O)C[C@H]3N(CC[C@]25[C@H]3CC4)C
InChI
  • InChI=1S/C17H20N4O2/c1-21-7-6-17-10-3-4-11(19-20-18)16(17)23-15-13(22)5-2-9(14(15)17)8-12(10)21/h2,5,10-12,16,22H,3-4,6-8H2,1H3/t10-,11+,12+,16-,17-/m0/s1 checkY
  • Key:KZOKOEQTKWBKOK-XHQKLZHNSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.[2]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 binds with high affinity to the mu opioid receptor,[3] and is around 40× 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. S2CID 41506653.
  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. S2CID 29580383.
  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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