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Sinomenine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Sinomenine
Clinical data
Other namesCocculine
ATC code
  • none
Identifiers
  • (9α,13α,14α)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.003.722Edit this at Wikidata
Chemical and physical data
FormulaC19H23NO4
Molar mass329.396 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 orcocculine is analkaloid found in the root of the climbing plantSinomenium acutum which is native to Japan and China. The plant is traditionally used inherbal medicine in these countries forrheumatism andarthritis.[1] However, analgesic action against other types of pain seems to be limited. Sinomenine is amorphinan derivative that is related to the common cough suppressantdextromethorphan. The drug's anti-rheumatic effects are thought to be primarily mediated via release ofhistamine,[2] but other effects such as inhibition ofprostaglandin,leukotriene andnitric oxide synthesis may also be involved.[3]

See also

[edit]

References

[edit]
  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.
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAATooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
Receptor
(ligands)
GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
(blockers)
GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2
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