sinomenine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 343554475

| IUPAC_name = (9α,13α,14α)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one

| image = Sinomenine structure.svg

| tradename =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 115-53-7

| CAS_supplemental =

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

| UNII = 63LT81K70N

| ATC_prefix = none

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| PubChem = 5459308

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

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| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 248095

| synonyms = Cocculine

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

| ChemSpiderID = 10179905

| chemical_formula =

| C=19 | H=23 | N=1 | O=4

| smiles = CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC

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

| StdInChI = 1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1

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

| StdInChIKey = INYYVPJSBIVGPH-QHRIQVFBSA-N

}}

Sinomenine or cocculine is an alkaloid found in the root of the climbing plant Sinomenium acutum which is native to Japan and China. The plant is traditionally used in herbal medicine in these countries for rheumatism and arthritis.{{cite journal | vauthors = Zhao ZZ, Liang ZT, Zhou H, Jiang ZH, Liu ZQ, Wong YF, Xu HX, Liu L | display-authors = 6 | title = Quantification of sinomenine in caulis sinomenii collected from different growing regions and wholesale herbal markets by a modified HPLC method | journal = Biological & Pharmaceutical Bulletin | volume = 28 | issue = 1 | pages = 105–9 | date = January 2005 | pmid = 15635172 | doi = 10.1248/bpb.28.105 | doi-access = free }} However, analgesic action against other types of pain seems to be limited. Sinomenine is a morphinan derivative that is related to the common cough suppressant dextromethorphan. The drug's anti-rheumatic effects are thought to be primarily mediated via release of histamine,{{cite journal | vauthors = Yamasaki H | title = Pharmacology of sinomenine, an anti-rheumatic alkaloid from Sinomenium acutum | journal = Acta Medica Okayama | volume = 30 | issue = 1 | pages = 1–20 | date = February 1976 | pmid = 61710 }} but other effects such as inhibition of prostaglandin, leukotriene and nitric oxide synthesis may also be involved.{{cite journal | vauthors = Liu L, Riese J, Resch K, Kaever V | title = Impairment of macrophage eicosanoid and nitric oxide production by an alkaloid from Sinomenium acutum | journal = Arzneimittel-Forschung | volume = 44 | issue = 11 | pages = 1223–6 | date = November 1994 | pmid = 7848335 }}