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

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)

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]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)

veratramine(60-70-8)Related Product Information

• Phoxim
• 2-(4-BIPHENYL)ETHYLAMINE
• 3,4-DIMETHYLPHENETHYLAMINE
• veratramine
• Benzeneethanamine, -alpha--ethyl-3-methyl-
• 3-(4-ISOBUTYL-PHENYL)-PROPAN-1-OL
• 4-(2,4-DIMETHYLPHENYL)-1-BUTENE
• 2-(4-METHYLBENZYL)PIPERIDINE
• 2-[4-(2-CYCLOHEXYL-ETHYL)-PHENYL]-ETHYLAMINE
• trimethylcumene
• 1,4-DI-ISO-PROPYL-2-METHYLBENZENE
• 1-(4-METHYL-PHENYL)-2-BUTANAMINE
• VERATROSINE
• Amfepentorex
• 3-(4-ISOPROPYL-PHENYL)-PROPAN-1-OL
• 1-(3-METHYLPHENYL)-4-METHYL-3-PENTENE
• 2-(3-METHYLBENZYL)PIPERIDINE
• RARECHEM AN KB 0358