Anpirtoline

Anpirtoline
Clinical data
Other names	D-16949; 6-Chloro-2-[piperidinyl-4-thio]pyridine
Drug class	Serotonin receptor modulator Serotonin 5-HT1B receptor agonist
Identifiers
	IUPAC name 2-chloro-6-piperidin-4-ylsulfanylpyridine;
CAS Number	98330-05-3;
PubChem CID	65854;
ChemSpider	59266;
UNII	32K9S228IK;
ChEBI	CHEBI:92968;
ChEMBL	ChEMBL1316374;
CompTox Dashboard (EPA)	DTXSID7045659 ;
Chemical and physical data
Formula	C10H13ClN2S
Molar mass	228.74 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CNCCC1SC2=NC(=CC=C2)Cl;
	InChI InChI=1S/C10H13ClN2S/c11-9-2-1-3-10(13-9)14-8-4-6-12-7-5-8/h1-3,8,12H,4-7H2; Key:GGALEXMXDMUMDM-UHFFFAOYSA-N;

Anpirtoline (INNTooltip International Nonproprietary Name; developmental code name D-16949), also known as 2-chloro-6-piperidin-4-ylsulfanylpyridine, is a serotonin receptor modulator which was under development for the treatment of major depressive disorder (MDD) and pain but was never marketed.

It is a serotonin 5-HT_1B and 5-HT_1D receptor agonist, a serotonin 5-HT_1A receptor ligand, a serotonin 5-HT₃ receptor antagonist, and also binds to the serotonin 5-HT₂ receptors with weak affinity. However, it acts preferentially as a serotonin 5-HT_1B receptor agonist and is sometimes described as being selective in this action. It causes a decrease in serotonin synthesis and a reduction in aggressive behavior.

Anpirtoline is a synthetic compound. Anpirtoline hydrochloride appears as a white solid and is soluble in water. Being synthetic, the compound can be purchased from suppliers.