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Revision as of 08:03, 1 July 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified and watched fields - updated 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot|b← Previous edit Latest revision as of 12:07, 25 March 2024 edit undoDMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,457 edits auto mw 
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{{Short description|Chemical compound}}
{{drugbox
{{Drugbox
| Verifiedfields = changed
⚫ | verifiedrevid = 437196684
| Watchedfields = changed
⚫ | IUPAC_name = (2''S'')-3-ethynyl-5-(1-methylpyrrolidin-2-yl)pyridine
⚫ | UNII_Ref = {{fdacite|changed|FDA}}
| image = Altinicline.svg
⚫ | UNII = RJ9V9V09VM
| width = 175
⚫ | verifiedrevid = 413848414

⚫ |IUPAC_name = (2S)-3-ethynyl-5-(1-methylpyrrolidin-2-yl)pyridine
<!--Clinical data-->
| image=Altinicline_structure.png
| width= 240 | tradename =
⚫ | routes_of_administration =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
⚫ | CAS_number = 179120-92-4
⚫ | ATC_prefix = None
⚫ | ATC_suffix =
⚫ | PubChem = 3036156
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2300234 | ChemSpiderID = 2300234
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
| InChI = 1/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
⚫ | UNII = RJ9V9V09VM
| InChIKey = NUPUDYKEEJNZRG-LBPRGKRZBN
| smiles1 = n1cc(cc(C#C)c1)2N(C)CCC2
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 111659 | ChEMBL = 111659

<!--Chemical data-->
⚫ | C=12 | H=14 | N=2
⚫ | smiles = c2ncc(C#C)cc2C1CCCN1C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NUPUDYKEEJNZRG-LBPRGKRZSA-N | StdInChIKey = NUPUDYKEEJNZRG-LBPRGKRZSA-N
⚫ | CAS_number= 179120-92-4
⚫ | ATC_prefix= None
⚫ | ATC_suffix=
⚫ | PubChem= 3036156
| DrugBank=
⚫ | C=12 | H=14 | N=2
| molecular_weight = 186.252
⚫ | smiles = c2ncc(C#C)cc2C1CCCN1C
| bioavailability=
| metabolism =
| elimination_half-life=
| excretion =
| pregnancy_category =
| legal_status =
⚫ | routes_of_administration=
}} }}


'''Altinicline''' ('''SIB-1508Y''') is a drug which acts as an ] at neural ]s with high selectivity for the ] subtype.<ref>{{Cite pmid|10812948}}</ref><ref>{{Cite pmid|17064057}}</ref> It stimulates release of ] and ] in the brain in both rodent and primate models,<ref>{{Cite pmid|18692487}}</ref> and progressed as far as Phase II ] for ],<ref>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}}</ref> although its current status is unclear. '''Altinicline''' ('''SIB-1508Y''', '''SIB-1765F''') is a drug which acts as an ] at neural ]s with high selectivity for the ] subtype.<ref>{{cite journal | vauthors = Cosford ND, Bleicher L, Vernier JM, Chavez-Noriega L, Rao TS, Siegel RS, Suto C, Washburn M, Lloyd GK, McDonald IA | display-authors = 6 | title = Recombinant human receptors and functional assays in the discovery of altinicline (SIB-1508Y), a novel acetylcholine-gated ion channel (nAChR) agonist | journal = Pharmaceutica Acta Helvetiae | volume = 74 | issue = 2–3 | pages = 125–30 | date = March 2000 | pmid = 10812948 | doi = 10.1016/S0031-6865(99)00024-2 }}</ref><ref>{{cite journal | vauthors = Wagner FF, Comins DL | title = Expedient five-step synthesis of SIB-1508Y from natural nicotine | journal = The Journal of Organic Chemistry | volume = 71 | issue = 22 | pages = 8673–5 | date = October 2006 | pmid = 17064057 | doi = 10.1021/jo0616052 }}</ref> It stimulates release of ] and ] in the brain in both rodent and primate models,<ref>{{cite journal | vauthors = Rao TS, Adams PB, Correa LD, Santori EM, Sacaan AI, Reid RT, Cosford ND | title = Pharmacological characterization of (S)-(2)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine HCl (SIB-1508Y, Altinicline), a novel nicotinic acetylcholine receptor agonist | journal = Brain Research | volume = 1234 | pages = 16–24 | date = October 2008 | pmid = 18692487 | doi = 10.1016/j.brainres.2008.07.063 | s2cid = 23547813 }}</ref> and progressed as far as Phase II ] for ],<ref name="pmid16476941">{{cite journal | author = The Parkinson Study Group | title = Randomized placebo-controlled study of the nicotinic agonist SIB-1508Y in Parkinson disease | journal = Neurology | volume = 66 | issue = 3 | pages = 408–10 | date = February 2006 | pmid = 16476941 | doi = 10.1212/01.wnl.0000196466.99381.5c | s2cid = 31720763 }}</ref> where "no antiparkinsonian or cognitive-enhancing effects were demonstrated", although its current status is unclear.

==Chemistry==
]

{{Cite journal|doi=10.1021/jo0616052|pmid=17064057|title=Expedient Five-Step Synthesis of SIB-1508Y from Natural Nicotine|year=2006|last1=Wagner|first1=Florence F.|last2=Comins|first2=Daniel L.|journal=The Journal of Organic Chemistry|volume=71|issue=22|pages=8673}}


== References == == References ==
{{Reflist|2}} {{Reflist}}



{{Stimulants}} {{Stimulants}}
{{Nootropics}}
{{Cholinergics}}


{{Nicotinic acetylcholine receptor modulators}}

⚫ {{nervous-system-drug-stub}}


] ]
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] ]
] ]
] ]


⚫ {{nervous-system-drug-stub}}