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Altinicline

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(Redirected fromSIB-1508Y)

Chemical compound

Pharmaceutical 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
PubChemCID	3036156
ChemSpider	2300234^Y
UNII	RJ9V9V09VM
ChEMBL	ChEMBL111659^Y
CompTox Dashboard(EPA)	DTXSID40870143
Chemical and physical data
Formula	C₁₂H₁₄N₂
Molar mass	186.258 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 anagonist at neuralnicotinic acetylcholine receptors with high selectivity for theα4β2 subtype.^[1]^[2] It stimulates release ofdopamine andacetylcholine in the brain in both rodent and primate models,^[3] and progressed as far as Phase IIclinical trials forParkinson's disease,^[4] where "no antiparkinsonian or cognitive-enhancing effects were demonstrated", although its current status is unclear.

References

[edit]

^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.
^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.
^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.
^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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Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
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Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Phenethylpyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPEP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
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Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code:N06B

Nicotinic acetylcholine receptor modulators

nAChRsTooltip Nicotinic acetylcholine receptors

Agonists
(and PAMsTooltip positive allosteric modulators)

Antagonists
(and NAMsTooltip negative allosteric modulators)

Precursors
(andprodrugs)

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

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