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Rutaecarpine (also known as rutecarpine; Rutacarpine; Rutaecarpin; Rhetine) is a naturally occuring indolopyridoquinazolinone alkaloid isolated from isolated from the chinese herb Evodia rutaecarpa which has vasorelaxing effect and inhibits platelet aggregation and Cox-2. It is alos a selective inhibitor of CYP1A1(cytochrome P450 1A).
Physicochemical Properties
| Molecular Formula | C18H13N3O | |
| Molecular Weight | 287.32 | |
| Exact Mass | 287.105 | |
| CAS # | 84-26-4 | |
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| PubChem CID | 65752 | |
| Appearance | Light yellow to yellow solid powder | |
| Density | 1.5±0.1 g/cm3 | |
| Boiling Point | 550.1±60.0 °C at 760 mmHg | |
| Melting Point | 259.5 - 260ºC | |
| Flash Point | 286.5±32.9 °C | |
| Vapour Pressure | 0.0±1.5 mmHg at 25°C | |
| Index of Refraction | 1.792 | |
| LogP | 2.03 | |
| Hydrogen Bond Donor Count | 1 | |
| Hydrogen Bond Acceptor Count | 2 | |
| Rotatable Bond Count | 0 | |
| Heavy Atom Count | 22 | |
| Complexity | 517 | |
| Defined Atom Stereocenter Count | 0 | |
| InChi Key | ACVGWSKVRYFWRP-UHFFFAOYSA-N | |
| InChi Code | InChI=1S/C18H13N3O/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/h1-8,19H,9-10H2 | |
| Chemical Name | 8,13-dihydro-indolo[2,3:3,4]pyrido[2,1-b]quinazolin-5(7H)-one | |
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| HS Tariff Code | 2934.99.9001 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Numerous intriguing biological characteristics of rupine have been demonstrated, including impacts on the endocrine and cardiovascular systems, antithrombotic, anticancer, anti-inflammatory and analgesic, anti-obesity and thermoregulatory, and vasodilatory activities [2]. With an IC50 of 0.28 μM and 8.7 μM, respectively, rutaecarpine suppresses the COX-2 and COX-1-dependent phases of PGD2 synthesis in BMMC in a concentration-dependent manner. It inhibits in a dose-dependent manner the COX-2-dependent conversion of exogenous arachidonic acid to PGE2 by COX-2-transfected HEK293 cells [1]. |
| ln Vivo | Rats' paw edema caused by L-carrageenan was treated with an intraperitoneal injection of evodiamine, which demonstrated in vivo anti-inflammatory action [1]. Rupine induced a dose-dependent decrease in the number of antibody-forming cells as well as a drop in spleen weight. Furthermore, animals with evodiamine displayed decreased spleen cellularity as well as decreased splenic total T cells, CD4+ cells, CD8+ cells, and B cells. IL-2, interferon, and IL-10 mRNA expression were all markedly suppressed by evodiamine therapy. Following rupine administration to mice, there was a considerable decrease in the quantity of CD4+IL-2+ cells [3]. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites Rutaecarpine has known human metabolites that include 3-Hydroxyrutaecarpine, 6-Hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4(9),5,7,15,17,19-octaen-14-one, 5-Hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4(9),5,7,15,17,19-octaen-14-one, 8-Hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4(9),5,7,15,17,19-octaen-14-one, 11-hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one, and 7-Hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4(9),5,7,15,17,19-octaen-14-one. |
| References |
[1]. A new class of COX-2 inhibitor, rutaecarpine from Evodia rutaecarpa. Inflamm Res. 1999 Dec;48(12):621-5. [2]. Progress in the studies on rutaecarpine. Molecules. 2008 Feb 6;13(2):272-300. [3]. Immunosuppressive effects of rutaecarpine in female BALB/c mice. Toxicol Lett. 2006 Jul 1;164(2):155-66. |
| Additional Infomation |
Rutecarpine is a member of beta-carbolines. Rutaecarpine has been reported in Tetradium ruticarpum, Zanthoxylum wutaiense, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4804 mL | 17.4022 mL | 34.8044 mL | |
| 5 mM | 0.6961 mL | 3.4804 mL | 6.9609 mL | |
| 10 mM | 0.3480 mL | 1.7402 mL | 3.4804 mL |