Pozanicline

Pozanicline

Identifiers
IUPAC name 2-Methyl-3-{[(2S)-pyrrolidin-2-yl]methoxy}pyridine
CAS Number	161417-03-4 checkY
PubChem CID	178052
ChemSpider	155000 ☒N
UNII	CL2002R563
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C11H16N2O
Molar mass	192.262 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C=CC=N1)OC[C@@H]2CCCN2
InChI InChI=1S/C11H16N2O/c1-9-11(5-3-6-12-9)14-8-10-4-2-7-13-10/h3,5-6,10,13H,2,4,7-8H2,1H3/t10-/m0/s1 ☒N Key:YRVIKLBSVVNSHF-JTQLQIEISA-N ☒N
☒NcheckY (what is this?)  (verify)

Pozanicline (INN, codenamed ABT-089) is a drug developed by Abbott, that has nootropic and neuroprotective effects. Animal studies suggested it useful for the treatment of ADHD and subsequent human trials have shown ABT-089 to be effective for this application. It binds with high affinity subtype-selective to the α₄β₂ nicotinic acetylcholine receptors and has partial agonism to the α₆β₂ subtype, but not the α₇ and α₃β₄ subtypes familiar to nicotine. It has particularly low tendency to cause side effects compared to other drugs in the class.

Synthesis

Pozanicline is synthesized from 2-methyl-3-hydroxypyridine and Boc-L-Prolinol through a dehydration reaction followed by deprotection of the nitrogen atom of prolinol