A-85380

A-85380 is a chemical compound that acts as a potent and selective agonist of nicotinic acetylcholine receptors (nAChRs), particularly the α4β2 subtype. It has been primarily used in scientific research to explore the structure and function of neuronal nAChRs and their role in neurodegenerative diseases, addiction, and cognition.^[1][2]

A-85380

Clinical data
Other names	A 85380, A85380, A-159470.
Identifiers
IUPAC name 3-(2-azetidinylmethoxy)pyridine
CAS Number	161416-98-4 2xHCl salt: 174740-86-4
PubChem CID	5310969
IUPHAR/BPS	5460
ChemSpider	4470513
ChEBI	CHEBI:230867
ChEMBL	ChEMBL59986
Chemical and physical data
Formula	C9H12N2O
Molar mass	164.208 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CN[C@@H]1COC2=CN=CC=C2
InChI InChI=1S/C9H12N2O/c1-2-9(6-10-4-1)12-7-8-3-5-11-8/h1-2,4,6,8,11H,3,5,7H2/t8-/m0/s1 Key:XKFMBGWHHBCWCD-QMMMGPOBSA-N

Synthesis

A-85380 synthesis:^[3]

The Mitsunobu reaction between (S)-1-Boc-2-azetidinemethanol [161511-85-9] (1) and 3-hydroxypyridine [109-00-2] (2) gives Tert-butyl (2S)-2-(pyridin-3-yloxymethyl)azetidine-1-carboxylate, PC10801571 (3). Acid deprotection of the urethane completed the synthesis of A-85380 (4).

See also

• Tebanicline
• Ropanicant