veratramine Property

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

Safety

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P405Store locked up.

veratramine Chemical Properties,Usage,Production

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]¹⁹_D - 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]^14.5_D + 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]²⁷_D + 27.4°, which forms the N-acetyl compound, m.p. 220-3°C; [α]²⁸_D + 81° and the triacetyl derivative, m.p. l89.5-190.5°C; [α]²⁴_D + 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)