Veratramine

Catalog Number	ACM60708
CAS Number	60-70-8
Structure
Synonyms	(3b,23b)-14,15,16,17-Teradehydroveratraman-3,23-diol
Molecular Weight	409.6
InChI	InChI=1S/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/t15-,17-,19-,22-,24-,25+,26-,27-/m0/s1
InChI Key	MALFODICFSIXPO-KFKQDBFTSA-N
Melting Point	122-124 °C
Purity	95%+
Complexity	676
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	8
Exact Mass	409.298079487
Heavy Atom Count	30
Hydrogen Bond Acceptor Count	3
Hydrogen Bond Donor Count	3
Isomeric SMILES	C[C@H]1C[C@H]([C@@H](NC1)[C@@H](C)C2=C(C3=C(C=C2)[C@@H]4CC=C5C[C@H](CC[C@@]5([C@H]4C3)C)O)C)O
Monoisotopic Mass	409.298079487
PhysicalState	Powder
Rotatable Bond Count	2
Topological Polar Surface Area	52.5 Ų

Case Study

Veratramine-Type Alkaloids with Potent Analgesic Properties

Li, Qiong, et al. Journal of ethnopharmacology, 2019, 244, 112137.

Veratramine-type alkaloids exhibit a variety of biological activities, such as anti-tumor, anti-hypertensive and anti-platelet aggregation pharmacological activities. This work isolated and characterized seven new veratridine-type steroidal alkaloids with analgesic properties from Veratrum taliense.
Extraction and isolation of veratramine-type alkaloids
· The roots and rhizomes (10 kg) of V. taliense were air-dried, powdered, and then extracted with MeOH at room temperature. The resulting MeOH extracts (2.0 kg) were combined, concentrated, and acidified with 0.5% hydrochloric acid (10:1 v/v). The mixture was filtered to separate the non-alkaloid part from the acidic aqueous fraction. The acidic aqueous fraction was then treated with 0.5% aqueous ammonia until reaching a pH of 9-10, and partitioned with EtOAc to yield an alkaloidal fraction (400 g).
· The alkaloidal fraction was further separated using silica gel column chromatography (CC) with varying ratios of CHCl3-MeOH elution. Subsequent fractionation of the second fraction (56 g) using RP-18 column chromatography with a MeOH-H2O gradient solvent system produced four subfractions (Fr. II-1 to Fr. II-4).
· Fr. II-1 (3 g) and Fr. II-2 (2 g) were purified through silica gel CC eluting with CHCl3-MeOH and CHCl3-acetone, respectively, resulting in the isolation of compound 2 (140 mg) and compound 3 (94 mg).
· Fr. II-3 (10 g) was divided into three sub-fractions (Fr. II-3-1 to Fr. II-3-3) by CC silica gel elution with CHCl3-MeOH. Fr. II-3-1 (2 g) was chromatographed over an RP-18 column eluting with CH3CN-H2O to yield compound 1 (2.5 mg).
· Fr. II-3-2 (500 mg) and Fr. II-3-3 (2 g) were subjected to RP-18 column chromatography to isolate compounds 4, 5, 6, and 7 using varying ratios of CH3CN-H2O as the eluting solvent.

Custom Q&A

What is the chemical formula for Veratramine?

The chemical formula for Veratramine is C27H39NO2.

What is the molecular weight of Veratramine?

The molecular weight of Veratramine is 409.6.

What is the melting point of Veratramine?

The melting point of Veratramine is 122-124 degrees Celsius.

In what form is Veratramine soluble?

Veratramine is soluble in DMSO (up to 12 mg/ml) or in Ethanol (up to 10 mg/ml).

How should Veratramine be stored?

Veratramine should be sealed in dry, stored in a freezer, under -20 degrees Celsius.

What is the HazardClass of Veratramine?

The HazardClass of Veratramine is 6.1.

What is Veratramine used for?

Veratramine is useful as a signal transduction inhibitor for treating tumors.

What is the hedgehog signaling pathway blocked by?

The hedgehog (Hh) signaling pathway is blocked by cyclopamine.

What is the role of Veratramine in inhibiting platelet aggregation in rabbits ex vivo?

Veratramine dose dependently inhibits platelet aggregation in rabbits ex vivo.

What chemical properties does Veratramine have?

Veratramine is a white solid with chemical properties that include two non-phenolic hydroxyl groups and an imino group.

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