Basic information Safety Supplier Related

veratramine

Basic information Safety Supplier Related

veratramine Basic information

Product Name:
veratramine
Synonyms:
  • veratramine
  • Vreaframine
  • (3b,23b)-14,15,16,17-Teradehydroveratraman-3,23-diol
  • NSC 17821
  • NSC 2388
  • Veratramine (NSC17821
  • Veratramine, >99%
  • Veratramine 60-70-8
CAS:
60-70-8
MF:
C27H39NO2
MW:
409.6
Product Categories:
  • Alkaloids
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
60-70-8.mol
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veratramine Chemical Properties

Melting point:
122-1240C
alpha 
D25 -71.8° (c = 1.21); D25 -70° (c = 1.56 in methanol)
Boiling point:
529.83°C (rough estimate)
Density 
1.0393 (rough estimate)
refractive index 
1.6400 (estimate)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
Soluble in DMSO (up to 12 mg/ml) or in Ethanol (up to 10 mg/ml)
pka
14.82±0.60(Predicted)
form 
solid
color 
Tan
λmax
268nm(lit.)
Merck 
14,9952
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
CAS DataBase Reference
60-70-8
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Safety Information

RIDADR 
UN 2811 6.1/PG III
RTECS 
YX5094000
HS Code 
2933.39.4100
HazardClass 
6.1
PackingGroup 
III
Hazardous Substances Data
60-70-8(Hazardous Substances Data)
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veratramine Usage And Synthesis

Description

This alkaloid occurs naturally in Veratrum grandi/lorum and V. viride and is also formed during the hydrolysis of Veratrosine (q.v.). It forms colourless crystals of the monohydrate from aqueous EtOH and has [α]19D - 70° (MeOH). The hydrochloride forms colourless plates from EtOH, m.p. 20l-2°C and the picrate, yellow plates, m.p. 217.5 - 218°C. Two non-phenolic hydroxyl groups and an imino group are present and the triacetyl derivative, m.p. 205.5-206°C; [α]14.5D + 37.8° (MeOH), on controlled hydrolysis furnishes the N-acetyl com_x0002_pound, m.p. 176-8°C. The O-acetate has also been prepared as colourless prisms from aqueous EtOH, m.p. 20l-2°C but it is still uncertain which of the hydroxyl groups is acetylated in this derivative. Treatment with methyl iodide in MeOH in the presence of sodium carbonate gives N-methylveratraminc methiodide, m.p. 268°C (dec.) from which the methochloride, m.p. 277°C can be obtained. On catalytic hydrogenation, the base furnishes the dihydro derivative, m.p. 198- 200°C; [α]27D + 27.4°, which forms the N-acetyl compound, m.p. 220-3°C; [α]28D + 81° and the triacetyl derivative, m.p. l89.5-190.5°C; [α]24D + 84°.

Chemical Properties

White Solid

Uses

It is useful as signal transduction inhibitor for treating tumors

Uses

The hedgehog (Hh) signaling pathway, which is blocked by cyclopamine , plays a key role in morphogenesis and has potential applications in the treatment of cancer. Veratramine, a teratogenic steroidal alkaloid isolated from the corn lily (Veratrum sp.), is an analog of cyclopamine that can inhibit the Hh signaling-dependent proliferation of NIH/3T3 cells at 8 μM. Additionally, veratramine has anti-thrombotic activity as it dose dependently inhibits platelet aggregation in rabbits ex vivo. While it may be most useful as a signal transduction inhibitor for treating tumors, veratramine also induces serotonin release and inhibits its re-uptake in the CNS.

Definition

ChEBI: A piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions.

References

Saito., Bull. Chem. Soc., Japan, 15, 22 (1940)
Jacobs, Craig.,J. Biol. Chem., 155,565 (1944)
Jacobs,.Craig., ibid, 160,555 (1945)
Tamm, Wintersteiner., J. Amer. Chem. Soc., 74,3842 (1952)
Mass spectra: Budzikiwicz., Tetrahedron, 20,2267 (1964)
Synthesis: Masamune, Takasugi, Murai., Tetrahedron, 27,3369 (1971)

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