Sinomenine

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 03:46, 8 September 2016 (Updating {{infobox_drug}} (changes to verified and watched fields - updated 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/infobox_drug validation (report errors or [[user ta...). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Sinomenine
Clinical data
Other namesCocculine
ATC code
  • none
Identifiers
  • (+)-4-Hydroxy-3,7-dimethoxy-17-methylmorphin-7-en-6-one
CAS Number
PubChem CID
ChemSpider
ChEMBL
ECHA InfoCard100.003.722 Edit this at Wikidata
Chemical and physical data
FormulaC19H23NO4
Molar mass329.390 g/mol g·mol−1
3D model (JSmol)
  • CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC
  • InChI=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 ☒N
  • Key:INYYVPJSBIVGPH-QHRIQVFBSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Sinomenine or cocculine is an alkaloid found in the root of the climbing plant Sinomenium acutum which is native to Japan and China. It is traditionally used in herbal medicine in these countries, as a treatment for rheumatism and arthritis.[1] However, its analgesic action against other kinds of pain is limited. Sinomenine is a morphinan derivative, related to opioids such as levorphanol and the non-opioid cough suppressant dextromethorphan. Its anti-rheumatic effects are thought to be primarily mediated via release of histamine,[2] but other effects such as inhibition of prostaglandin, leukotriene and nitric oxide synthesis may also be involved.[3]

See also

References

  1. ^ Zhao, ZZ; Liang, ZT; Zhou, H; Jiang, ZH; Liu, ZQ; Wong, YF; Xu, HX; Liu, L (2005). "Quantification of sinomenine in caulis sinomenii collected from different growing regions and wholesale herbal markets by a modified HPLC method". Biological & Pharmaceutical Bulletin. 28 (1): 105–9. doi:10.1248/bpb.28.105. PMID 15635172.
  2. ^ Yamasaki, H (1976). "Pharmacology of sinomenine, an anti-rheumatic alkaloid from Sinomenium acutum". Acta medica Okayama. 30 (1): 1–20. PMID 61710.
  3. ^ Liu, L; Riese, J; Resch, K; Kaever, V (1994). "Impairment of macrophage eicosanoid and nitric oxide production by an alkaloid from Sinomenium acutum". Arzneimittel-Forschung. 44 (11): 1223–6. PMID 7848335.