Rivanicline

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
Chemical and physical data
Formula	C10H14N2
Molar mass	162.232
3D model (Jmol)	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,^[1][2] 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.^[3] Rivanicline also has stimulant and analgesic actions which are thought to be mediated through stimulation of noradrenaline release,^[4] and so it could potentially also have other applications.

References

1. Jang J, Sin KS, Park H. Synthesis of (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines. Archives of Pharmacal Research. 2001 Dec;24(6):503-7. PMID 11794523
2. Sapronov NS, Fedotova YO, Kuznetsova NN. Antiamnestic effect of alpha7-nicotinic receptor agonist RJR-2403 in middle-aged ovariectomized rats with Alzheimer type dementia. Bulletin of Experimental Biology and Medicine. 2006 Dec;142(6):700-2. PMID 17603674
3. Spoettl T, Paetzel C, Herfarth H, Bencherif M, Schoelmerich J, Greinwald R, Gatto GJ, Rogler G. (E)-metanicotine hemigalactarate (TC-2403-12) inhibits IL-8 production in cells of the inflamed mucosa. International Journal of Colorectal Disease. 2007 Mar;22(3):303-12. PMID 16715250
4. Li X, Eisenach JC. Nicotinic acetylcholine receptor regulation of spinal norepinephrine release. Anesthesiology. 2002 Jun;96(6):1450-6. PMID 12170059