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);Rutecarpine (8CI);7,8-dihydroindolo[2′,3′:3,4]pyrido[2,1-b]quinazolin-5(13H)-one;RHETINE;8,13-DIHYDRO-INDOLO[2’3′:3,4]PYRIDO[2,1-B]QUINAZOLIN-5(7H)-ONE;RUTECARPINE 95+;Rutaecarpine std.
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 Structure
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
pka15.79±0.20(Predicted)
color white
Merck 14,8298
InChIKeyACVGWSKVRYFWRP-UHFFFAOYSA-N
CAS DataBase Reference84-26-4(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 Information
ProviderLanguage
RutaecarpineEnglish
SigmaAldrichEnglish
Rutaecarpine Usage And Synthesis
DescriptionThis 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 PropertiesSolid
UsesRutaecarpine 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
DefinitionChEBI: Rutecarpine is a member of beta-carbolines.
ReferencesAsahina, 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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