Structure via PubChem · Public domain (PubChem)
azaprocin
Sign in to saveAzaprocin 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. It was discovered in 1963, but has never been marketed.
Chemical data
- Formula
- C18H24N2O
- Molecular weight
- 284.4 g/mol
- IUPAC name
- 1-[(1R,5R)-3-[(E)-3-phenylprop-2-enyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]propan-1-one
- SMILES
- CCC(=O)N1[C@@H]2CC[C@@H]1CN(C2)C/C=C/C3=CC=CC=C3
- InChIKey
- RKNSPEOBXHFNTD-QOCAVEGASA-N
- XLogP
- 2.8
- Polar surface area
- 23.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 284.18886338799996
Show 4 more facts
- isomeric SMILES
- CCC(=O)N1[C@@H]2CC[C@@H]1CN(C2)C/C=C/C3=CC=CC=C3
- chemical formula
- C₁₈H₂₄N₂O
- canonical SMILES
- CCC(=O)N1C2CCC1CN(CC=Cc1ccccc1)C2
- Commons category
- Azaprocin
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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. It was discovered in 1963, but has never been marketed.
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. The ring-opened 2,6-dimethylpiperazine analogues are also active, and a large family of opioid analgesic compounds derived from this parent structure have been developed over the last 40 years. One analogue, AP-237, has been used in China to treat the pain caused by cancer.
Excerpted from Wikipedia’s “azaprocin” article, available under the CC BY-SA 4.0 licence.