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CAS NO.84-26-4
98%(1-25)Kilogram98%(26-500)Kilogram98%(501-1000)Kilogram
rutecarpine
CAS: 84-26-4
Molecular Formula: C18H13N3O
| Name | rutecarpine |
| Synonyms | RHETINE RUTECARPINE Rutacarpine rutecarpine Rutaecarpine Rutecarpine (8CI) |
| CAS | 84-26-4 |
| EINECS | 635-907-6 |
| InChI | InChI=1/C18H15N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,17,19-20H,9-10H2 |
| InChIKey | ACVGWSKVRYFWRP-UHFFFAOYSA-N |
| Molecular Formula | C18H13N3O |
| Molar Mass | 287.32 |
| Density | 1.2030 (rough estimate) |
| Melting Point | 259.5-260° |
| Boling Point | 429.62°C (rough estimate) |
| Specific Rotation(α) | +350°(acetone) |
| Flash Point | 313.753°C |
| Solubility | Soluble in acetone, slightly soluble in ethanol, ether, chloroform, almost insoluble in water, petroleum ether, benzene. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White crystal |
| Color | white |
| Merck | 14,8298 |
| pKa | 15.79±0.20(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.5855 (estimate) |
| MDL | MFCD00210551 |
| Physical and Chemical Properties | Soluble in acetone, ethanol-soluble, ether, chloroform, almost insoluble in water, petroleum ether, benzene. Dry, nearly mature fruit from Evodia rutaecarpa (Jess.)Benth. |
| Overview | rutaecarpine (Rut) is derived from the traditional Chinese medicine Evodiarutaecarpa(Juss) chemical monomer extracted from. Fructus evodiae is a traditional Chinese medicine for the treatment of hypertension, angina pectoris and so on, which is widely used. Fructus evodiae is its main active ingredient. Studies have shown that evodiamine has anti-hypertension, anti-cancer, anti-inflammatory, anti-thrombosis and other pharmacological effects, which indicates that it has the prospect of developing new monomer drugs, at present, many scholars are committed to the development of a new mechanism of anti-hypertension and anti-inflammatory drugs. Image: Evodia fructus |
| synthesis | at present, the methods for synthesizing Rut are as follows: 1: The raw materials of this method are easily available, and the reaction conditions are mild, A series of derivatives can be obtained by changing the type of lactam, and the crude product can be purified by recrystallization from ethanol. Rut was synthesized by this method, and the yield was 92%. figure: synthetic route Two: Rut was obtained by using isatoic anhydride as raw material through 7-step reaction, with long reaction time and many steps, the target product reported in the literature is only Rut, no other derivatives, the yield is 30% Three: with isatoic anhydride as raw material, after 4 steps of reaction, Rut is obtained, the conditions are mild, the time is short, in the literature, the synthesis of the target product can be substituted on the benzene ring to obtain derivatives, and the yield is low. IV: O-aminobenzamide and Glutaric anhydride as raw materials. The yield of Rut was 34.6% over the 6-step reaction. The conditions were mild and the time was long. |
| metabolism research | Rut can effectively induce the activities of CYP1A 1 and CYP1A2 in the liver, rut can induce CYP2B in the liver of mice. Rut is a mechanism inhibitor of CYP3A 4: ①the inhibitory effect of Rut on CYP3A 4 depends on the pre-incubation time; ②The inhibitory effect needs NAD-PH; ③The competitive inhibitor of CYP3A 4 ketoconazole could attenuate the inhibitory effect of Rut; ④The activity of CYP3A 4 inhibited by Rut could not be restored by permeabilization. |
| pharmacological effects | cardiovascular system effects: Ru t can enhance the protective effect of crystalloid cardioplegia, its role can be canceled by capsazep ine and CGRP8 ~ 37. In addition, Rut has protective effect on allergic injury of isolated guinea pig heart and increases the level of CGRP in coronary effluent, pretreatment with CGRP8 -37 can abrogate the protective effects of Rut on the heart. Rut has a wide range of cardioprotective effects that are associated with activation of the capsaicin receptor and promotion of CGRP release. In addition, the hypotensive and vasodilatory effects of Rut are mainly related to the Ca2-NO-cGMP pathway of endothelial cells, and are also related to the reduction of intracellular calcium in smooth muscle cells. The hypotensive and vasodilative effects of Rut are related to the activation of capsaicin receptors and the promotion of CGRP release. effects on the digestive system: in vitro experiments showed that Rut could antagonize the contractile effects of acetylcholine or histamine on the isolated ileum of guinea pigs. In addition, the protective effect of Rut on gastric mucosa may be related to the activation of capsaicin receptor and the promotion of CGRP release. Rut can inhibit colitis in mice by Diarrhea, reduce the intestinal weight index, reduce the colitis damage, reduce the colon tissue myeloperoxidase and prostaglandin (PG)E2 content. effects on the nervous system: Rut could reduce the infarct size, promote the recovery of brain function and increase the concentration of CGRP in ischemic area in a dose-dependent manner. The researchers suggest that the protective effect of Rut may be related to the increase of CGRP concentration. In addition, studies have shown that Rut can block the delayed rectifier potassium channel of NG108-15 nerve cells, and prolong the action potential duration. antiplatelet: the antiplatelet effect of Rut is related to the inhibition of phospholipase C activity, reduction of inositol phosphate degradation, inhibition of thromboxane production, and thus inhibition of platelet calcium mobilization. In vivo experiments in mice also showed that Rut could effectively inhibit platelet and arterial thrombosis. Anti-inflammatory and analgesic effects: Studies on rats and mice have shown that Rut has significant anti-inflammatory and anti-nociceptive effects. In addition, Rut reduced the colitis injury and the levels of myeloperoxidase and PGE2 in animals with ulcerative colitis. The anti-inflammatory effect of Rut was related to its inhibition of arachidonic acid release and prostaglandin synthesis. Anti-cancer effect: Rut can inhibit the binding of TCDD receptor to the four oxygen two benzene two oxygen heterocyclic ring (TC DD), and inhibit the benzopyrene 7, Mutagenicity of 8-dihydrodiol pem2 cells, which is associated with Rut's inhibition of cytochrome P450( CYP)1A1. Studies on mouse and human liver microsomes have confirmed that Ru t can selectively inhibit CYP1A, and its inhibitory effect on CYP1A2 is stronger than that on CYPAl. Many pre-carcinogens need to be converted into electrophilic compounds by CYP to ultimately exert a carcinogenic effect, therefore, Rut may have an anti-cancer effect. |
| references | [1] Yu Qi, Guo Cheng, Cheng zeneng. Research progress of evodiamine [J]. Journal of Pharmaceutical Practice, 2007, 25(6):353-357. [2] Duan Xu, Ling Feng. Pharmacological effects of secondary alkaloids from Evodia [J]. Chinese Journal of Traditional Chinese Medicine, 2007, 25 (9):1857-1859. [3] Li Yingying. Study on the mechanism and pharmacokinetics of the regulation of glucose and lipid metabolism by activating CAR [D]. Zhejiang University, 2016. [4] Liu Baolin, Wu Weiwei, Jin Changfeng, et al. Therapeutic effect of evodiamine on ulcerative colitis in mice [J]. Chinese Journal of Clinical Pharmacology and Therapeutics, 2004, 9(11):1273-1277. [5] Wu Hai. Study on absorption mechanism of secondary alkaloids from fructus evodiae [D]. Sichuan University, 2007. |
| Use | for content determination/identification/pharmacological experiments. Pharmacological Efficacy: anti-hypertensive, anti-arrhythmia, the role of the excited uterus. delayed rectifier potassium channel blockers. Inhibition of platelet aggregation; Vasodilator. |
Mol Download Chemical properties
CAS:
84-26-4
MF:
C18H13N3O
MW:
287.32
EINECS:
635-907-6
MDL No.:
MFCD00210551
Melting point:
259.5-260°
Boiling point:
429.62°C (rough estimate)
Density
1.2030 (rough estimate)
refractive index
1.5855 (estimate)
storage temp.
Sealed in dry,2-8°C
solubility
DMSO: 18 mg/mL clear yellow solution, soluble
form
solid
pka
15.79±0.20(Predicted)
color
white
Merck
14,8298
InChIKey
ACVGWSKVRYFWRP-UHFFFAOYSA-N
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