60-70-8

Basic information

• Product Name: veratramine
• Synonyms: veratramine;Vreaframine;(3b,23b)-14,15,16,17-Teradehydroveratraman-3,23-diol;NSC 17821;NSC 2388;AIDS011940;(3,23)-14,15,16,17-Teradehydroveratraman-3,23-diol;NSC 23880
• CAS NO: 60-70-8
• Molecular Formula: C27H39NO2
• Molecular Weight: 409.61
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Alkaloids
• Mol File: 60-70-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 122-1240C
• Boiling Point: 529.83°C (rough estimate)
• Flash Point: 86.2°C
• Appearance: /
• Density: 1.0393 (rough estimate)
• Vapor Pressure: 1.33E-13mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: Soluble in DMSO (up to 12 mg/ml) or in Ethanol (up to 10 mg/ml)
• PKA: 14.82±0.60(Predicted)
• 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.
• Merck: 14,9952
• CAS DataBase Reference: veratramine(CAS DataBase Reference)
• NIST Chemistry Reference: veratramine(60-70-8)
• EPA Substance Registry System: veratramine(60-70-8)

Safety Data

• RIDADR: UN 2811 6.1/PG III
• RTECS: YX5094000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 60-70-8(Hazardous Substances Data)

Usage

Description

Veratramine is a teratogenic steroidal alkaloid derived from the corn lily (Veratrum sp.), specifically from Veratrum grandi/florum and V. viride. It is an analog of cyclopamine and occurs as a white solid. Veratramine has unique chemical properties, including two non-phenolic hydroxyl groups and an imino group. It forms colorless crystals of the monohydrate from aqueous ethanol and has various derivatives with distinct melting points and optical rotations.

Uses

Used in Pharmaceutical Industry:
Veratramine is used as a signal transduction inhibitor for treating tumors. It inhibits the Hedgehog (Hh) signaling pathway, which plays a crucial role in morphogenesis and has potential applications in cancer treatment. Veratramine can inhibit the Hh signaling-dependent proliferation of NIH/3T3 cells at 8 μM, making it a promising candidate for cancer therapy.
Used in Cardiovascular Applications:
Veratramine has anti-thrombotic activity, as it dose-dependently inhibits platelet aggregation in rabbits ex vivo. This property makes it potentially useful in the development of treatments for thrombotic disorders and related cardiovascular conditions.
Used in Central Nervous System (CNS) Applications:
Veratramine induces serotonin release and inhibits its re-uptake in the CNS. This dual action suggests potential applications in the treatment of neurological and psychiatric disorders, particularly those involving serotonin dysregulation, such as depression and anxiety.

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)

InChI:InChI=1/C27H39NO2/c1-15-11-25(30)26(28-14-15)17(3)20-7-8-21-22-6-5-18-12-19(29)9-10-27(18,4)24(22)13-23(21)16(20)2/h5,7-8,15,17,19,22,24-26,28-30H,6,9-14H2,1-4H3

Relevant articles and documents

Establishment of the C9 configuration of jervine and related alkaloids. Structure of the Birch reduction products of "jervine-11 beta-ol" and 11-deoxojervine.

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