Identification | Back Directory | [Name]
SINOMENINE HYDROCHLORIDE | [CAS]
6080-33-7 | [Synonyms]
SINOMENINE HCL Cucoline hydrochloride Kukoline hydrochloride Sinomenine Hydrocloride Tuduranine Hydrochloride SINOMENINE HYDROCHLORIDE Sabianine A hydrochloride Sinomenine Hydrochloride > (9α,13α,14α)- 7,8-Didehydro-4-
hydroxy-3,7-diMet Sinomenine hydrochloride (Cucoline hydrochloride) TIANFU-CHEM CAS:6080-33-7 SINOMENINE HYDROCHLORIDE hydroxy-dimethoxy-methyl-BLAH-azatetracyclo[BLAH]hexadeca-BLAH,BLAH,BLAH,BLAH-tetraenone (9a,13a,14a)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one hydrochloride 7,8-Didehydro-4-hydroxy-3,7-diMethoxy-17-Methyl-
9α,13α,14α-Morphinan-6-one Hydrochloride 9α,13α,14α-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, hydrochloride | [EINECS(EC#)]
618-347-7 | [Molecular Formula]
C19H24ClNO4 | [MDL Number]
MFCD01714307 | [MOL File]
6080-33-7.mol | [Molecular Weight]
365.85 |
Chemical Properties | Back Directory | [Melting point ]
231.0 to 235.0 °C | [storage temp. ]
2-8°C | [solubility ]
H2O: soluble20mg/mL, clear | [form ]
powder | [color ]
white to beige | [optical activity]
[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| |
Hazard Information | Back Directory | [Description]
Sinomenine is a natural plant alkaloid commonly used to alleviate inflammation associated with rheumatoid arthritis.1 It activates histamine release, reduces joint stiffness and pain, and alters cytokine generation without producing gastrointestinal adverse events.1,2,3,4 Sinomenine also impairs signaling through NF-κB, resulting in immunosuppression as well as reduced inflammation and pain.3,1 It enhances the bioavailability of some compounds, at least in part through an inhibition of drug export by transporters like P-glycoprotein.5,6 | [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.] |
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