Azidomorphine

Azidomorphine

Skeletal formula of azidomorphine
Space-filling model of the azidomorphine molecule
Clinical data
Other names	Azidomorphine
ATC code	none
Identifiers
IUPAC name (6β)-Azido-4,5-α-epoxy-17-methyl morphinan-3-ol
CAS Number	22952-87-0 ☒N
PubChem CID	5488848
ChemSpider	4590009 checkY
UNII	U973VU74ER
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C17H20N4O2
Molar mass	312.373 g·mol−1
3D model (JSmol)	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 checkY Key:KZOKOEQTKWBKOK-XHQKLZHNSA-N checkY
☒NcheckY (what is this?)  (verify)

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analogue that is a derivative of morphine, where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an azide group.

Azidomorphine binds with high affinity to the mu opioid receptor, 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.