Azidomorphine

Azidomorphine

Systematic (IUPAC) name
(6β)-Azido-4,5-α-epoxy-17-methyl morphinan-3-ol
Clinical data
Legal status	?
Identifiers
CAS Number	22952-87-0
ATC code	none
PubChem	CID 5488848
ChemSpider	4590009
Synonyms	Azidomorphine
Chemical data
Formula	C17H20N4O2
Molar mass	312.366 g/mol
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analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.^[2]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.