IUPAC_name = (E)-N-Methyl-4-(3-pyridinyl)-3-butene-1-amine

width= 240
CAS_number= 538-79-4
PubChem= 5310967
C=10 | H=14 | N=2
molecular_weight = 162.232
smiles = CNCCC=CC1=CN=CC=C1
metabolism =
excretion =
pregnancy_category =
legal_status =

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, [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] [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] 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. [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] Rivanicline also has stimulant and analgesic actions which are thought to be mediated through stimulation of noradrenaline release, [Li X, Eisenach JC. Nicotinic acetylcholine receptor regulation of spinal norepinephrine release. "Anesthesiology". 2002 Jun;96(6):1450-6. PMID 12170059] and so it could potentially also have other applications.


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