Tebanicline

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.^[1][2] 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.^{[3][4][5][6][7][8]} It acts as a partial agonist at neuronal nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes.^[9]

Tebanicline

Clinical data
ATC code	none
Identifiers
IUPAC name 5-{[(2R)-Azetidin-2-yl]methoxy}-2-chloropyridine
CAS Number	198283-73-7 Y
PubChem CID	3075702
IUPHAR/BPS	3989
ChemSpider	2334347 N
UNII	9KX8NKV538
ChEMBL	ChEMBL430497 N
CompTox Dashboard (EPA)	DTXSID90173555
ECHA InfoCard	100.207.679
Chemical and physical data
Formula	C9H11ClN2O
Molar mass	198.65 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CN[C@H]1COC2=CN=C(C=C2)Cl
InChI InChI=1S/C9H11ClN2O/c10-9-2-1-8(5-12-9)13-6-7-3-4-11-7/h1-2,5,7,11H,3-4,6H2/t7-/m1/s1 N Key:MKTAGSRKQIGEBH-SSDOTTSWSA-N N
NY (what is this?)  (verify)

Tebanicline progressed to Phase II clinical trials in humans,^[10] but was dropped from further development due to unacceptable incidence of gastrointestinal side effects.^[11] However, further research in this area is ongoing,^{[12][13][14][15]} and the development of nicotinic acetylcholine receptor agonists is ongoing.^{[16][17][18][19]} No agents from this class have successfully completed human clinical trials due to their unacceptable side effect profiles. Research in the area continues.^[20]