Rutaecarpine
Rutaecarpine Basic information
- Product Name:
- Rutaecarpine
- Synonyms:
-
- :3,4]pyrido[2,1-b]quinazolin-5(7H)-one
- Indolo(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13-dihydro- (9CI)
- Rutacarpine
- Rutecarpine (8CI)
- 7,8-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one
- RHETINE
- RUTECARPINE
- 8,13-DIHYDRO-INDOLO[2'3':3,4]PYRIDO[2,1-B]QUINAZOLIN-5(7H)-ONE
- CAS:
- 84-26-4
- MF:
- C18H13N3O
- MW:
- 287.32
- EINECS:
- 635-907-6
- Product Categories:
-
- chemical reagent
- pharmaceutical intermediate
- phytochemical
- reference standards from Chinese medicinal herbs (TCM).
- standardized herbal extract
- Indoles and derivatives
- Inhibitors
- Mol File:
- 84-26-4.mol
Rutaecarpine Chemical Properties
- 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
- InChI
- 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
- InChIKey
- ACVGWSKVRYFWRP-UHFFFAOYSA-N
- SMILES
- N1C2=C(C=CC=C2)C(=O)N2CCC3C4=C(NC=3C=12)C=CC=C4
- CAS DataBase Reference
- 84-26-4(CAS DataBase Reference)
Safety Information
- Hazard Codes
- T
- Risk Statements
- 25-36/37/38
- Safety Statements
- 45-36-26
- RIDADR
- UN 2811 6.1/PG 3
- WGK Germany
- 3
- RTECS
- NM3454000
- HS Code
- 29339900
MSDS
- Language:English Provider:Rutaecarpine
- Language:English Provider:SigmaAldrich
Rutaecarpine Usage And Synthesis
Description
This alkaloid occurs with Evodiamine (q.v.) in the Chinese drug 'Wou-chou-yu'
which is the dried fruit of Evodia rutaecarpa Benth. It crystallizes from boiling
EtOH as colourless, or pale yellow, needles and is optically inactive. The acetyl
derivative has m.p. 184-6°C and the benzoyl compound, m.p. 194°C. The
alkaloid gives a yellow colour with concentrated H2S04 and is decomposed by
KOH in boiling amyl alcohol yielding anthranilic acid and 3-{3-aminoethylindole-
2-O!carboxylic acid, CllH120 2N2, silky crystals, m.p. 257°C.
Pharmacologically, the alkaloid causes increased arterial pressure on injection.
Chemical Properties
Solid
Uses
Rutaecarpine is an indole alkaloid contained in the fruit of Evodiae fruits. It been shown to ameliorate bodyweight gain through orexigenic neuropeptides NPY and AgRP. It also playes a role in the treatment of high blood pressure
Definition
ChEBI: Rutecarpine is a member of beta-carbolines.
in vivo
Rutaecarpine showed in vivo anti-inflammatory activity on rat l-carrageenan induced paw edema by intraperitoneal administration[1]. Rutaecarpine significantly decreases the number of antibody-forming cells and causes weight decrease in spleen in a dose-dependent manner. In addition, rutaecarpine administered mice exhibit reduced splenic cellularity, decreased numbers of total T cells, CD4+ cells, CD8+ cells, and B cells in spleen. IL-2, interferon and IL-10 mRNA expressions are suppressed significantly by rutaecarpine treatment. The number of CD4+IL-2+ cells is reduced significantly following administration of mice with rutaecarpine[3].
IC 50
COX-2: 0.28 μM (IC50, in BMMC); COX-1: 8.7 μM (IC50, in BMMC)
References
Asahina, Kashiwagi., J. Pharm. Chim., 14,54 (1916)
Asahina, Mayeda.,J. Pharm. Soc., Japan, No. 416 (1916)
Asahina, Fujita., ibid, 863 (1921)
Kermack, Perkin, Robinson.,J. Chem. Soc., 119,1615 (1921)
Asahina, Manske, Robinson., ibid, 1708 (1927)
Asahina, Irie, Ohta., J. Pharm. Soc., Japan, 48, 51 (1928)
Ohta., ibid, 60, 109 (1940)
Schopf, Steuer., Annalen, 558, 124 (1947)
Biosynthesis:
Yamazaki, Ikuta., Tetrahedron Lett., 3221 (1966)
Yamazakietal., ibid, 3317 (1967)
Pharmacology:
Raymond-Hamet., Cornpt. rend., 220, 749 (1945)
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