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Rivanicline

Clinical data
ATC code	none
Identifiers
IUPAC name (E)-N-Methyl-4-(3-pyridinyl)-3-butene-1-amine
CAS Number	15585-43-0 538-79-4 (Mixture E of Z)
PubChem CID	5310967
IUPHAR/BPS	3994
ChemSpider	4470511
UNII	6H35LF645A
CompTox Dashboard (EPA)	DTXSID101017740
Chemical and physical data
Formula	C10H14N2
Molar mass	162.236 g·mol
3D model (JSmol)	Interactive image
SMILES CNCC\C=C\C1=CN=CC=C1
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+ Key:JUOSGGQXEBBCJB-GORDUTHDSA-N
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Rivanicline (TC-2403, RJR-2403, (E)-metanicotine) is a drug which acts as a partial agonist at neural nicotinic acetylcholine receptors. It is subtype-selective, binding primarily to the α4β2 subtype. It has nootropic effects and was originally developed as a potential treatment for Alzheimer's disease, but a second action that was subsequently found was that it inhibits the production of Interleukin-8 and thus produces an antiinflammatory effect, and so it has also been developed as a potential treatment for ulcerative colitis. Rivanicline also has stimulant and analgesic actions which are thought to be mediated through stimulation of noradrenaline release, and so it could also have other applications. It has been identified as constituent of tobacco as well.

See also

• Ispronicline

References

1. Bencherif M, Byrd G, Caldwell WS, Hayes JR, Lippiello PM (1997). "Pharmacological Characterization of RJR-2403: A Nicotinic Agonist with Potential Therapeutic Benefit in the Treatment of Alzheimer's Disease". CNS Drug Reviews. 3 (4). Wiley: 325–345. doi:10.1111/j.1527-3458.1997.tb00331.x. ISSN 1080-563X.
2. Jang J, Sin KS, Park H (December 2001). "Synthesis of (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines". Archives of Pharmacal Research. 24 (6): 503–7. doi:10.1007/bf02975153. PMID 11794523. S2CID 19502452.
3. Sapronov NS, Fedotova YO, Kuznetsova NN (December 2006). "Antiamnestic effect of alpha7-nicotinic receptor agonist RJR-2403 in middle-aged ovariectomized rats with Alzheimer type dementia". Bulletin of Experimental Biology and Medicine. 142 (6): 700–2. doi:10.1007/s10517-006-0455-y. PMID 17603674. S2CID 7186817.
4. Spoettl T, Paetzel C, Herfarth H, Bencherif M, Schoelmerich J, Greinwald R, et al. (March 2007). "(E)-metanicotine hemigalactarate (TC-2403-12) inhibits IL-8 production in cells of the inflamed mucosa". International Journal of Colorectal Disease. 22 (3): 303–12. doi:10.1007/s00384-006-0135-4. PMID 16715250. S2CID 11135872.
5. Li X, Eisenach JC (June 2002). "Nicotinic acetylcholine receptor regulation of spinal norepinephrine release". Anesthesiology. 96 (6): 1450–6. doi:10.1097/00000542-200206000-00026. PMID 12170059. S2CID 3473611.
6. Stedman RL (April 1968). "The chemical composition of tobacco and tobacco smoke". Chemical Reviews. 68 (2). American Chemical Society (ACS): 153–207. doi:10.1021/cr60252a002. PMID 4868017.
7. "Effect of gibberellic acid applications to leaves of Nicotiana on nornicotine, anabasine, metanicotine, oxynicotine, and nicotinic acid content". {{cite journal}}: Cite journal requires |journal= (help)

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