Sinomenine

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.[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]

Sinomenine
Clinical data
Other namesCocculine
ATC code
  • none
Identifiers
IUPAC name
  • (9α,13α,14α)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.003.722
Chemical and physical data
FormulaC19H23NO4
Molar mass329.396 g·mol−1
3D model (JSmol)
SMILES
  • CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC
InChI
  • 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
 NY (what is this?)  (verify)

See also
  • Hasubanan
  • Oreobeiline

References
  1. Zhao ZZ, Liang ZT, Zhou H, Jiang ZH, Liu ZQ, Wong YF, et al. (January 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 (February 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 (November 1994). "Impairment of macrophage eicosanoid and nitric oxide production by an alkaloid from Sinomenium acutum". Arzneimittel-Forschung. 44 (11): 1223–6. PMID 7848335.
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