Altinicline

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.

Altinicline
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • (2S)-3-ethynyl-5-(1-methylpyrrolidin-2-yl)pyridine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC12H14N2
Molar mass186.252 g·mol−1
3D model (JSmol)
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)

References
  1. Cosford ND, Bleicher L, Vernier JM, Chavez-Noriega L, Rao TS, Siegel RS, et al. (March 2000). "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. doi:10.1016/S0031-6865(99)00024-2. PMID 10812948.
  2. Wagner FF, Comins DL (October 2006). "Expedient five-step synthesis of SIB-1508Y from natural nicotine". The Journal of Organic Chemistry. 71 (22): 8673–5. doi:10.1021/jo0616052. PMID 17064057.
  3. Rao TS, Adams PB, Correa LD, Santori EM, Sacaan AI, Reid RT, Cosford ND (October 2008). "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. doi:10.1016/j.brainres.2008.07.063. PMID 18692487. S2CID 23547813.
  4. 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. S2CID 31720763.


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