Structure via PubChem · Public domain (PubChem)
tebanicline
Sign in to saveAlso known as 5-[[(2R)-azetidin-2-yl]methoxy]-2-chloropyridine, ebanicline, ABT-594
Tebanicline (ebanicline, ABT-594) is a potent synthetic nicotinic (non-opioid) analgesic drug developed by Abbott. It was developed as a less toxic analog of the potent poison dart frog-derived compound epibatidine, which is about 200 times stronger than morphine as an analgesic, but produces extremely dangerous toxic side effects. Like epibatidine, tebanicline showed potent analgesic activity against neuropathic pain in both animal and human trials, but with far less toxicity than its parent compound. It acts as a partial agonist at neuronal nicotinic acetylcholine receptors, binding to both
Chemical data
- Formula
- C9H11ClN2O
- Molecular weight
- 198.65 g/mol
- IUPAC name
- 5-[[(2R)-azetidin-2-yl]methoxy]-2-chloropyridine
- SMILES
- C1CN[C@H]1COC2=CN=C(C=C2)Cl
- InChIKey
- MKTAGSRKQIGEBH-SSDOTTSWSA-N
- XLogP
- 1.6
- Polar surface area
- 34.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 198.055990652
Show 4 more facts
- isomeric SMILES
- C1CN[C@H]1COC2=CN=C(C=C2)Cl
- chemical formula
- C₉H₁₁ClN₂O
- canonical SMILES
- C1CNC1COC2=CN=C(C=C2)Cl
- Commons category
- Tebanicline
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Analogs
- See also
- References
{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 448113374 | IUPAC_name = 5-{[(2R)-Azetidin-2-yl]methoxy}-2-chloropyridine | image = Tebanicline.svg | image_class = skin-invert-image
| tradename = | routes_of_administration =
Excerpted from Wikipedia’s “tebanicline” article, available under the CC BY-SA 4.0 licence.