rivanicline   

GtoPdb Ligand ID: 3994

Synonyms: metanicotine | RJR-2403 | TC 2403 | TC-2403 | TC2403 | trans-metanicotine
Compound class: Synthetic organic
Comment: Rivanicline is an agonist at neural nicotinic acetylcholine receptors, binding primarily to the α4β2 subtype [1]. Potential clinical use of rivanicline is discussed in patent US5616707 [2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 24.92
Molecular weight 162.12
XLogP 1.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CNCCC=Cc1cccnc1
Isomeric SMILES CNCC/C=C/c1cccnc1
InChI InChI=1S/C10H14N2/c1-11-7-3-2-5-10-6-4-8-12-9-10/h2,4-6,8-9,11H,3,7H2,1H3/b5-2+
InChI Key JUOSGGQXEBBCJB-GORDUTHDSA-N
References
1. Bencherif M, Lovette ME, Fowler KW, Arrington S, Reeves L, Caldwell WS, Lippiello PM. (1996)
RJR-2403: a nicotinic agonist with CNS selectivity I. In vitro characterization.
J. Pharmacol. Exp. Ther., 279 (3): 1413-21. [PMID:8968366]
2. Crooks PA, Caldwell WS, Dull GM, Bhatti BS, Deo NM, Ravard A. (1997)
Compounds which are useful for prevention and treatment of central nervous system disorders.
Patent number: US5616707 A. Assignee: Crooks PA, Caldwell WS, Dull GM, Bhatti BS, Deo NM, Ravard A.. Priority date: 01/12/2015. Publication date: 01/04/1997.
3. Dogruer D, Lee M, Dukat M, Damaj MI, Martin BR, Glennon RA. (2004)
3-(4-Aminobutyn-1-yl)pyridines: binding at alpha 4 beta 2 nicotinic cholinergic receptors.
Bioorg. Med. Chem. Lett., 14 (2): 523-6. [PMID:14698195]