Sinomenine

Drugbox
IUPAC_name = (+)-4-hydroxy-3,7-dimethoxy-17-methylmorphin-7-en-6-one


CAS_number = 115-53-7
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PubChem = 5459308
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chemical_formula =
C=19 | H=23 | N=1 | O=4
molecular_weight = 329.390 g/mol
smiles = CN1CC [C@@] 23CC(=O)C(=C [C@@H] 2 [C@@H] 1CC4=C3C(=C(C=C4)OC)O)OC
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Sinomenine 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. [Zhao ZZ, Liang ZT, Zhou H, Jiang ZH, Liu ZQ, Wong YF, Xu HX, Liu L. Quantification of sinomenine in caulis sinomenii collected from different growing regions and wholesale herbal markets by a modified HPLC method. "Biological and Pharmaceutical Bulletin". 2005 Jan;28(1):105-9. PMID 15635172] 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, [Yamasaki H. Pharmacology of sinomenine, an anti-rheumatic alkaloid from Sinomenium acutum. "Acta Medica Okayama". 1976 Feb;30(1):1-20. PMID 61710] but other effects such as inhibition of prostaglandin, leukotriene and nitric oxide synthesis may also be involved. [Liu L, Riese J, Resch K, Kaever V. Impairment of macrophage eicosanoid and nitric oxide production by an alkaloid from Sinomenium acutum. "Arzneimittelforschung". 1994 Nov;44(11):1223-6. PMID 7848335]

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