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| veratramine Basic information |
| 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 |
| 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) |
| veratramine Preparation Products And Raw materials |
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