|
|
| | SINOMENINE HYDROCHLORIDE Basic information |
| Product Name: | SINOMENINE HYDROCHLORIDE | | Synonyms: | hydroxy-dimethoxy-methyl-BLAH-azatetracyclo[BLAH]hexadeca-BLAH,BLAH,BLAH,BLAH-tetraenone;Sinomenine Hydrocloride;Cucoline hydrochloride;(9a,13a,14a)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one hydrochloride;SINOMENINE HYDROCHLORIDE;SINOMENINE HCL;(9α,13α,14α)- 7,8-Didehydro-4-
hydroxy-3,7-diMet;7,8-Didehydro-4-hydroxy-3,7-diMethoxy-17-Methyl-
9α,13α,14α-Morphinan-6-one Hydrochloride | | CAS: | 6080-33-7 | | MF: | C19H23NO4.ClH | | MW: | 365.85 | | EINECS: | 618-347-7 | | Product Categories: | Alkaloids;Inhibitors;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;chemical reagent;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;APIs | | Mol File: | 6080-33-7.mol |  |
| | SINOMENINE HYDROCHLORIDE Chemical Properties |
| Melting point | 231.0 to 235.0 °C | | storage temp. | Inert atmosphere,2-8°C | | solubility | H2O: soluble20mg/mL, clear | | form | powder | | color | white to beige | | Optical Rotation | [α]/D -70 to -90°, c = 1 in H2O | | Water Solubility | Soluble to 100 mM in water | | InChI | InChI=1/C19H23NO4.ClH/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;1H/t12-,13+,19-;/s3 | | InChIKey | YMEVIMJAUHZFMW-FSYSDVFBNA-N | | SMILES | OC1C(=CC=C2C[C@]3([H])N(CC[C@]4(CC(C(=C[C@@]43[H])OC)=O)C2=1)C)OC.Cl |&1:7,12,17,r| |
| Safety Statements | 24/25 | | WGK Germany | 3 | | RTECS | QD2163000 | | HS Code | 29334900 |
| | SINOMENINE HYDROCHLORIDE Usage And Synthesis |
| Description | Sinomenine is a natural plant alkaloid commonly used to alleviate inflammation associated with rheumatoid arthritis. It activates histamine release, reduces joint stiffness and pain, and alters cytokine generation without producing gastrointestinal adverse events. Sinomenine also impairs signaling through NF-κB, resulting in immunosuppression as well as reduced inflammation and pain. It enhances the bioavailability of some compounds, at least in part through an inhibition of drug export by transporters like P-glycoprotein. | | Chemical Properties | White Solid | | Uses | Sinomenine is an optical isomer of Methoxythebainone. Sinomenine was extracted from root of Sinomenium acutum. Sinomenine has anti-inflammatory and analgesic effect. | | in vivo | Sinomenine hydrochloride (i.p.) produces antinociception in the hot plate and tail flick tests in male rats at 40 mg/kg, but not at lower doses (10 or 20 mg/kg). At 10 to 40 mg/kg Sinomenine hydrochloride does not produce any observable side effect such as sedation, allergy or motor impairments. Sinomenine hydrochloride at 80 mg/kg i.p. does not produce any observable side effects in mice. I.p or p.o. Sinomenine hydrochloride at 40 or 80 mg/kg dose-dependently reduces mechanical hypersensitivity in nerve injured mice. I.p. Sinomenine hydrochloride at 40 mg/kg, but not lower doses or vehicle, significantly decreases mechanical and cold allodynia for up to 240 min without producing motor deficits or sedation[3]. At doses of 10 to 40 mg/kg, Sinomenine hydrochloride dose-dependently increases the paw withdrawal threshold. In non-chronic constriction injury (CCI) healthy rats, Sinomenine hydrochloride at the dose range of 10 to 40 mg/kg does not change the immobility behavior in the forced swimming test[4]. | | IC 50 | NF-κB; μ Opioid Receptor/MOR | | Purification Methods | Crystallise the salt from water (1g/1.5mL) or EtOH. The free base [115-53-7] M 329.4, has m 161o (from EtOH) (and again at 182o) after crystallisation from *C6H6, and [] D 20 -78.9o (c 1, EtOH). The picrate has m 159-162o(dec) (from H2O). [Beilstein 21 II 470, 21 III/IV 6670.] | | References | [1] QUANXING WANG Xiao K L. Immunosuppressive and anti-inflammatory activities of sinomenine[J]. International immunopharmacology, 2011, 11 3: Pages 373-376. DOI: 10.1016/j.intimp.2010.11.018
[2] MAYEDA H. THE SITE OF HISTAMINE RELEASE BY SINOMENINE*[J]. Japanese journal of pharmacology, 1954, 3 2: Pages 73-81. DOI: 10.1254/jjp.3.73
[3] YUE SUN Cong zhu D Yao Yao. A combination of Sinomenine and Methotrexate reduces joint damage of collagen induced arthritis in rats by modulating osteoclast-related cytokines[J]. International immunopharmacology, 2014, 18 1: Pages 135-141. DOI: 10.1016/j.intimp.2013.11.014
[4] MIN XU. Sinomenine versus NSAIDs for the treatment of rheumatoid arthritis: a systematic review and meta-analysis.[J]. Planta medica, 2008, 74 12: 1423-1429. DOI: 10.1055/s-2008-1081346
[5] KRITIKA KESARWANI Rajiv G. Bioavailability enhancers of herbal origin: An overview[J]. Asian Pacific journal of tropical biomedicine, 2013, 3 4: Pages 253-266. DOI: 10.1016/s2221-1691(13)60060-x
[6] ZHEN LIU. Sinomenine sensitizes multidrug-resistant colon cancer cells (Caco-2) to doxorubicin by downregulation of MDR-1 expression.[J]. PLoS ONE, 2014: e98560. DOI: 10.1371/journal.pone.0098560 |
| | SINOMENINE HYDROCHLORIDE Preparation Products And Raw materials |
|