Veratramine , ≥98% , 60-70-8

CAS NO.：60-70-8

Empirical Formula: C27H39NO2

Molecular Weight: 409.6

MDL number: MFCD00468124

PRODUCT 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)
• 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.
• InChIKey: MALFODICFSIXPO-KFKQDBFTSA-N
• SMILES: N1C[C@@H](C)C[C@@H](O)[C@@H]1[C@H](C1=C(C)C2C[C@@]3([H])[C@]([H])(C=2C=C1)CC=C1C[C@@H](O)CC[C@]31C)C
• CAS DataBase Reference: 60-70-8

Description and Uses

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°.

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.

Safety

• Symbol(GHS): GHS06
• Signal word: Danger
• Hazard statements: H301
• Precautionary statements: P501-P270-P264-P301+P310+P330-P405
• 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)