Azidomorphine

Azidomorphine

Clinical data
ATC code	none
Legal status
Legal status	?
Identifiers
IUPAC name (6β)-Azido-4,5-α-epoxy-17-methyl morphinan-3-ol
Synonyms	Azidomorphine
CAS Number	22952-87-0
PubChem (CID)	5488848
ChemSpider	4590009
Chemical and physical data
Formula	C17H20N4O2
Molar mass	312.366 g/mol
3D model (Jmol)	Interactive image
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 Key:KZOKOEQTKWBKOK-XHQKLZHNSA-N
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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analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.^[2]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 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. US patent 3880862, Meltzer, R. I., "6β-Azido-17-cycloalkylmethyl-4,5α-epoxymorphinan-3-ols", issued 1975-04-29, assigned to Warner-Lambert 
2. Knoll, J.; Fürst, S.; Kelemen, K. (1973). "The pharmacology of azidomorphine and azidocodeine". Journal of Pharmacy and Pharmacology. 25 (12): 929–939. doi:10.1111/j.2042-7158.1973.tb09982.x. PMID 4150295.
3. Horváth, K.; Wollemann, M. (1986). "Azidomorphine is an agonist of high-affinity opioid receptor binding sites". Neurochemical Research. 11 (11): 1565–1569. doi:10.1007/bf00965775. PMID 2825053.
4. Knoll, J. (1979). "Azidomorphines: A new family of potent analgesics with low dependence capacity". Progress in Neuropsychopharmacology. 3 (1–3): 95–108. doi:10.1016/0364-7722(79)90074-2. PMID 45567.
5. Hill, R. C.; Roemer, D.; Buescher, H. (1977). "Investigations of the analgesic and morphine-like properties of azidomorphine". Journal of Pharmacology and Experimental Therapeutics. 201 (3): 580–586. PMID 405472.