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Rivanicline

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Rivanicline
Skeletal formula
Ball-and-stick model of rivanicline
Clinical data
ATC code
  • none
Identifiers
  • (E)-N-Methyl-4-(3-pyridinyl)-3-butene-1-amine
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC10H14N2
Molar mass162.236 g·mol−1
3D model (JSmol)
  • CNCC\C=C\C1=CN=CC=C1
  • 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
 ☒NcheckY (what is this?)  (verify)

Rivanicline (TC-2403,RJR-2403,(E)-metanicotine) is a drug which acts as apartial agonist at neuralnicotinic acetylcholine receptors. It is subtype-selective, binding primarily to theα4β2subtype. It hasnootropic effects and was originally developed as a potential treatment forAlzheimer's disease,[1][2][3] but a second action that was subsequently found was that it inhibits the production ofInterleukin-8 and thus produces anantiinflammatory effect, and so it has also been developed as a potential treatment forulcerative colitis.[4] Rivanicline also hasstimulant andanalgesic actions which are thought to be mediated through stimulation ofnoradrenaline release,[5] and so it could also have other applications. It has been identified as constituent of tobacco as well.[6][7]

See also

[edit]

References

[edit]
  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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