Altinicline

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Altinicline
Altinicline structure.png
Systematic (IUPAC) name
(2S)-3-ethynyl-5-(1-methylpyrrolidin-2-yl)pyridine
Clinical data
Legal status ?
Identifiers
CAS number 179120-92-4 YesY
ATC code None
PubChem CID 3036156
ChemSpider 2300234 YesY
UNII RJ9V9V09VM YesY
ChEMBL CHEMBL111659 YesY
Chemical data
Formula C12H14N2 
Mol. mass 186.252
 YesY (what is this?)  (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] although its current status is unclear.

Chemistry[edit]

Altinicline synth.png


The diagram above demonstrates the five-step process of conversion from nicotine.[5]

References[edit]

  1. ^ Cosford, N. D.; Bleicher, L.; Vernier, J. M.; Chavez-Noriega, L.; Rao, T. S.; Siegel, R. S.; Suto, C.; Washburn, M.; Lloyd, G. K.; McDonald, I. A. (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): 125–130. doi:10.1016/S0031-6865(99)00024-2. PMID 10812948.  edit
  2. ^ Wagner, F.; Comins, D. (2006). "Expedient five-step synthesis of SIB-1508Y from natural nicotine". The Journal of Organic Chemistry 71 (22): 8673–8675. doi:10.1021/jo0616052. PMID 17064057.  edit
  3. ^ Rao, T.; Adams, P.; Correa, L.; Santori, E.; Sacaan, A.; Reid, R.; Cosford, N. (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.  edit
  4. ^ The Parkinson Study Group. Randomized placebo-controlled study of the nicotinic agonist SIB-1508Y in Parkinson disease. Neurology. 2006;66:408-410. doi:10.1212/01.wnl.0000196466.99381.5c
  5. ^ Wagner, Florence F.; Comins, Daniel L. (2006). "Expedient Five-Step Synthesis of SIB-1508Y from Natural Nicotine". The Journal of Organic Chemistry 71 (22): 8673. doi:10.1021/jo0616052. PMID 17064057.