Rivanicline

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 448113257

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

| image = Rivanicline.svg

| alt = Skeletal formula

| image2 = Rivanicline molecule ball.png

| alt2 = Ball-and-stick model of rivanicline

| width = 240

| tradename =

| routes_of_administration =

| IUPHAR_ligand = 3994

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 15585-43-0

| CAS_supplemental=
538-79-4 (Mixture E of Z)

| ATC_prefix = none

| ATC_suffix =

| PubChem = 5310967

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6H35LF645A

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4470511

| C=10 | H=14 | N=2

| smiles = CNCC\C=C\C1=CN=CC=C1

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = JUOSGGQXEBBCJB-GORDUTHDSA-N

}}

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,{{cite journal | vauthors = Bencherif M, Byrd G, Caldwell WS, Hayes JR, Lippiello PM | title=Pharmacological Characterization of RJR-2403: A Nicotinic Agonist with Potential Therapeutic Benefit in the Treatment of Alzheimer's Disease | journal=CNS Drug Reviews | publisher=Wiley | volume=3 | issue=4 | year=1997 | issn=1080-563X | doi=10.1111/j.1527-3458.1997.tb00331.x | pages=325–345| doi-access=free }}{{cite journal | vauthors = Jang J, Sin KS, Park H | title = Synthesis of (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines | journal = Archives of Pharmacal Research | volume = 24 | issue = 6 | pages = 503–7 | date = December 2001 | pmid = 11794523 | doi = 10.1007/bf02975153 | s2cid = 19502452 }}{{cite journal | vauthors = Sapronov NS, Fedotova YO, Kuznetsova NN | title = Antiamnestic effect of alpha7-nicotinic receptor agonist RJR-2403 in middle-aged ovariectomized rats with Alzheimer type dementia | journal = Bulletin of Experimental Biology and Medicine | volume = 142 | issue = 6 | pages = 700–2 | date = December 2006 | pmid = 17603674 | doi = 10.1007/s10517-006-0455-y | s2cid = 7186817 }} 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.{{cite journal | vauthors = Spoettl T, Paetzel C, Herfarth H, Bencherif M, Schoelmerich J, Greinwald R, Gatto GJ, Rogler G | display-authors = 6 | title = (E)-metanicotine hemigalactarate (TC-2403-12) inhibits IL-8 production in cells of the inflamed mucosa | journal = International Journal of Colorectal Disease | volume = 22 | issue = 3 | pages = 303–12 | date = March 2007 | pmid = 16715250 | doi = 10.1007/s00384-006-0135-4 | s2cid = 11135872 }} Rivanicline also has stimulant and analgesic actions which are thought to be mediated through stimulation of noradrenaline release,{{cite journal |author2-link=James C. Eisenach | vauthors = Li X, Eisenach JC | title = Nicotinic acetylcholine receptor regulation of spinal norepinephrine release | journal = Anesthesiology | volume = 96 | issue = 6 | pages = 1450–6 | date = June 2002 | pmid = 12170059 | doi = 10.1097/00000542-200206000-00026 | s2cid = 3473611 | doi-access = free }} and so it could also have other applications. It has been identified as constituent of tobacco as well.{{cite journal | vauthors = Stedman RL | title = The chemical composition of tobacco and tobacco smoke | journal = Chemical Reviews | volume = 68 | issue = 2 | pages = 153–207 | date = April 1968 | pmid = 4868017 | doi = 10.1021/cr60252a002 | publisher = American Chemical Society (ACS) }}{{cite journal|title=Effect of gibberellic acid applications to leaves of Nicotiana on nornicotine, anabasine, metanicotine, oxynicotine, and nicotinic acid content.|url=https://www.cabdirect.org/cabdirect/abstract/19610300895}}