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HomeProduct name listveratramine

veratramine

  • CAS NO.:60-70-8
  • Empirical Formula: C27H39NO2
  • Molecular Weight: 409.6
  • MDL number: MFCD00468124
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-06-08 17:06:34
veratramine Structural

What is veratramine?

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

The Uses of veratramine

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.

The Uses of veratramine

It is useful as signal transduction inhibitor for treating tumors

What are the applications of Application

Veratramine is a signal transduction inhibitor for treating tumors

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)

Properties of veratramine

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)
form  solid
pka 14.82±0.60(Predicted)
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

Safety information for veratramine

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P405:Store locked up.

Computed Descriptors for veratramine

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