Azaprocin

Azaprocin is a drug which is an opioid analgesic with approximately ten times the potency of morphine, and a fast onset and short duration of action.^[1][2][3] It was discovered in 1963, but has never been marketed.

Azaprocin

Clinical data
ATC code	none
Identifiers
IUPAC name 1-(3-((E)-3-Phenylprop-2-enyl)-3,8-diazabicyclo[3.2.1]octan-8-yl)propan-1-one
CAS Number	140844-23-1 Y
PubChem CID	6433185
ChemSpider	16736583 Y
UNII	D20F1K1BYP
ChEMBL	ChEMBL2105901 N
CompTox Dashboard (EPA)	DTXSID20161480
Chemical and physical data
Formula	C18H24N2O
Molar mass	284.403 g·mol−1
3D model (JSmol)	Interactive image
Melting point	170 to 175 °C (338 to 347 °F)
SMILES CCC(N1[C@@H]2CC[C@H]1CN(C2)C/C=C/C3=CC=CC=C3)=O
InChI InChI=1S/C18H24N2O/c1-2-18(21)20-16-10-11-17(20)14-19(13-16)12-6-9-15-7-4-3-5-8-15/h3-9,16-17H,2,10-14H2,1H3/b9-6+/t16-,17+ Y Key:RKNSPEOBXHFNTD-DQCUJPBYSA-N Y
NY (what is this?)  (verify)

Para-nitroazaprocin, the derivative substituted on the phenyl ring with a p-nitro group, is more potent than the parent compound, around 25× the potency of morphine.^[4] The ring-opened 2,6-dimethylpiperazine analogues are also active,^[5] and a large family of opioid analgesic compounds derived from this parent structure have been developed over the last 40 years.^{[6][7][8][9][10][11][12][13][14][15]} One analogue, AP-237, has been used in China to treat the pain caused by cancer.^{[citation needed]}