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Rutaecarpine

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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
  • Indoles and derivatives
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Inhibitors
Mol File:
84-26-4.mol
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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
InChIKey
ACVGWSKVRYFWRP-UHFFFAOYSA-N
CAS DataBase Reference
84-26-4(CAS DataBase Reference)
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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

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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.

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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