Chemistry:Altinicline

Short description: Chemical compound

Altinicline
Clinical data

ATC code	None
Identifiers
IUPAC name (2S)-3-ethynyl-5-(1-methylpyrrolidin-2-yl)pyridine
CAS Number	179120-92-4^Y
PubChem CID	3036156
ChemSpider	2300234^Y
UNII	RJ9V9V09VM
ChEMBL	ChEMBL111659^Y
Chemical and physical data
Formula	C₁₂H₁₄N₂
Molar mass	186.252 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c2ncc(C#C)cc2C1CCCN1C
InChI InChI=1S/C12H14N2/c1-3-10-7-11(9-13-8-10)12-5-4-6-14(12)2/h1,7-9,12H,4-6H2,2H3/t12-/m0/s1^Y Key:NUPUDYKEEJNZRG-LBPRGKRZSA-N^Y
(verify)

Altinicline (SIB-1508Y, SIB-1765F) is a drug which acts as an agonist at neural nicotinic acetylcholine receptors with high selectivity for the α4β2 subtype.^[1]^[2] It stimulates release of dopamine and acetylcholine in the brain in both rodent and primate models,^[3] and progressed as far as Phase II clinical trials for Parkinson's disease,^[4] where "no antiparkinsonian or cognitive-enhancing effects were demonstrated", although its current status is unclear.

References

↑ "Recombinant human receptors and functional assays in the discovery of altinicline (SIB-1508Y), a novel acetylcholine-gated ion channel (nAChR) agonist". Pharmaceutica Acta Helvetiae 74 (2–3): 125–30. March 2000. doi:10.1016/S0031-6865(99)00024-2. PMID 10812948.
↑ "Expedient five-step synthesis of SIB-1508Y from natural nicotine". The Journal of Organic Chemistry 71 (22): 8673–5. October 2006. doi:10.1021/jo0616052. PMID 17064057.
↑ "Pharmacological characterization of (S)-(2)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine HCl (SIB-1508Y, Altinicline), a novel nicotinic acetylcholine receptor agonist". Brain Research 1234: 16–24. October 2008. doi:10.1016/j.brainres.2008.07.063. PMID 18692487.
↑ The Parkinson Study Group (February 2006). "Randomized placebo-controlled study of the nicotinic agonist SIB-1508Y in Parkinson disease". Neurology 66 (3): 408–10. doi:10.1212/01.wnl.0000196466.99381.5c. PMID 16476941.

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ATC code: N06B