Rivanicline

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][3] 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.[4] Rivanicline also has stimulant and analgesic actions which are thought to be mediated through stimulation of noradrenaline release,[5] and so it could also have other applications. It has been identified as constituent of tobacco as well.[6][7]

Rivanicline
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (E)-N-Methyl-4-(3-pyridinyl)-3-butene-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
Chemical and physical data
FormulaC10H14N2
Molar mass162.232 g·mol−1
3D model (JSmol)
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+ N
  • Key:JUOSGGQXEBBCJB-GORDUTHDSA-N N
 NY (what is this?)  (verify)

See also

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. Wiley. 3 (4): 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. American Chemical Society (ACS). 68 (2): 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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