Veratramine

CAS# 60-70-8

Veratramine

Catalog No. BCN2965----Order now to get a substantial discount!

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Chemical structure

Veratramine

3D structure

Chemical Properties of Veratramine

Cas No. 60-70-8 SDF Download SDF
PubChem ID 6070 Appearance White powder
Formula C27H39NO2 M.Wt 409.6
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms NSC17821; NSC23880
Solubility DMSO : ≥ 100 mg/mL (244.14 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (2S,3R,5S)-2-[(1S)-1-[(3S,6aR,11aS,11bR)-3-hydroxy-10,11b-dimethyl-1,2,3,4,6,6a,11,11a-octahydrobenzo[a]fluoren-9-yl]ethyl]-5-methylpiperidin-3-ol
SMILES CC1CC(C(NC1)C(C)C2=C(C3=C(C=C2)C4CC=C5CC(CCC5(C4C3)C)O)C)O
Standard InChIKey MALFODICFSIXPO-KFKQDBFTSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Veratramine

The herbs of Veratrum nigrum L.

Biological Activity of Veratramine

DescriptionVeratramine exhibits cytotoxic activity against human tumor cell lines A549, PANC-1, SW1990 and NCI-H249. Veratramine shows hypotensive effect, the effect is directly positively correlated with the dosage.
In vitro

Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum.[Pubmed: 18570211 ]

Phytother Res. 2008 Aug;22(8):1093-6.


METHODS AND RESULTS:
The antitumor activity of six extracts (ethanol extract, petroleum ether fraction, CHCl(3) fraction, ethyl acetate fraction, n-butanol fraction and total alkaloids) from the rhizomes of Veratrum dahuricum, and six compounds (Veratramine (1), jervine (2), germine (3), veramitaline (4), veratrosine (5) and cyclopamine (6)) from the ethanol extract were investigated in vitro. The 12 samples exhibited cytotoxic activity against human tumor cell lines A549, PANC-1, SW1990 and NCI-H249.
CONCLUSIONS:
Among these samples, CHCl(3) fraction, the total alkaloids, compounds 1 and 6 showed higher inhibitory activity, compound 3 selectively exhibited significant cytotoxicity to SW1990 and NCI-H249.

In vivo

Hypotensive effect and toxicology of total alkaloids and veratramine from roots and rhizomes of Veratrum nigrum L. in spontaneously hypertensive rats.[Pubmed: 18771011]

Pharmazie. 2008 Aug;63(8):606-10.


METHODS AND RESULTS:
Total alkaloids (VTA) and Veratramine of Veratrum nigrum L. were tested for hypotensive effect using spontaneously hypertensive rats (SHR). Acute toxicities were also evaluated. There was a dose-dependent reduction in blood pressure and heart rate after a single ingestion (1.0 to 4.0 mg/kg, intragastric administration) of VTA. A single oral ingestion (0.56 to 2.24 mg/kg) of Veratramine, the major component of VTA, dose-dependently decreased blood pressure and heart rate, suggesting that Veratramine was involved in the hypotensive effect of VTA in SHR.
CONCLUSIONS:
The hypotensive effects of VTA and Veratramine are directly positively correlated with the dosage. Side effects were not obvious.

Gender-Dependent Pharmacokinetics of Veratramine in Rats: In Vivo and In Vitro Evidence.[Pubmed: 26791530]

AAPS J. 2016 Mar;18(2):432-44.

Veratramine, a major alkaloid from Veratrum nigrum L., has distinct anti-tumor and anti-hypertension effects. Our previous study indicated that Veratramine had severe toxicity toward male rats.
METHODS AND RESULTS:
In order to elucidate the underling mechanism, in vivo pharmacokinetic experiments and in vitro mechanistic studies have been conducted. Veratramine was administrated to male and female rats intravenously via the jugular vein at a dose of 50 μg/kg or orally via gavage at 20 mg/kg. As a result, significant pharmacokinetic differences were observed between male and female rats after oral administration with much lower concentrations of Veratramine and 7-hydroxyl-Veratramine and higher concentrations of Veratramine-3-O-sulfate found in the plasma and urine of female rats. The absolute bioavailability of Veratramine was 0.9% in female rats and 22.5% in male rats. Further experiments of Veratramine on Caco-2 cell monolayer model and in vitro incubation with GI content or rat intestinal subcellular fractions demonstrated that its efficient passive diffusion mediated absorption with minimal intestinal metabolism, suggesting no gender-related difference during its absorption process. When Veratramine was incubated with male or female rat liver microsomes/cytosols, significant male-predominant formation of 7-hydroxyl-Veratramine and female-predominant formation of Veratramine-3-O-sulfate were observed.
CONCLUSIONS:
In conclusion, the significant gender-dependent hepatic metabolism of Veratramine could be the major contributor to its gender-dependent pharmacokinetics.

Veratramine Dilution Calculator

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Preparing Stock Solutions of Veratramine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4414 mL 12.207 mL 24.4141 mL 48.8281 mL 61.0352 mL
5 mM 0.4883 mL 2.4414 mL 4.8828 mL 9.7656 mL 12.207 mL
10 mM 0.2441 mL 1.2207 mL 2.4414 mL 4.8828 mL 6.1035 mL
50 mM 0.0488 mL 0.2441 mL 0.4883 mL 0.9766 mL 1.2207 mL
100 mM 0.0244 mL 0.1221 mL 0.2441 mL 0.4883 mL 0.6104 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Veratramine

Veratramine(NSC17821; NSC23880) is useful as a signal transduction inhibitor for treating tumors.

References:
[1]. Wang L, et al. Hypotensive effect and toxicology of total alkaloids and veratramine from roots and rhizomes of Veratrum nigrum L. in spontaneously hypertensive rats. Pharmazie. 2008 Aug;63(8):606-10. [2]. Li HJ, et al. Puqienine F, a novel veratramine alkaloid from the bulbs of Fritillaria puqiensis. Chem Pharm Bull (Tokyo). 2006 May;54(5):722-4.

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References on Veratramine

Gender-Dependent Pharmacokinetics of Veratramine in Rats: In Vivo and In Vitro Evidence.[Pubmed:26791530]

AAPS J. 2016 Mar;18(2):432-44.

Veratramine, a major alkaloid from Veratrum nigrum L., has distinct anti-tumor and anti-hypertension effects. Our previous study indicated that Veratramine had severe toxicity toward male rats. In order to elucidate the underling mechanism, in vivo pharmacokinetic experiments and in vitro mechanistic studies have been conducted. Veratramine was administrated to male and female rats intravenously via the jugular vein at a dose of 50 mug/kg or orally via gavage at 20 mg/kg. As a result, significant pharmacokinetic differences were observed between male and female rats after oral administration with much lower concentrations of Veratramine and 7-hydroxyl-Veratramine and higher concentrations of Veratramine-3-O-sulfate found in the plasma and urine of female rats. The absolute bioavailability of Veratramine was 0.9% in female rats and 22.5% in male rats. Further experiments of Veratramine on Caco-2 cell monolayer model and in vitro incubation with GI content or rat intestinal subcellular fractions demonstrated that its efficient passive diffusion mediated absorption with minimal intestinal metabolism, suggesting no gender-related difference during its absorption process. When Veratramine was incubated with male or female rat liver microsomes/cytosols, significant male-predominant formation of 7-hydroxyl-Veratramine and female-predominant formation of Veratramine-3-O-sulfate were observed. In conclusion, the significant gender-dependent hepatic metabolism of Veratramine could be the major contributor to its gender-dependent pharmacokinetics.

Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum.[Pubmed:18570211]

Phytother Res. 2008 Aug;22(8):1093-6.

The antitumor activity of six extracts (ethanol extract, petroleum ether fraction, CHCl(3) fraction, ethyl acetate fraction, n-butanol fraction and total alkaloids) from the rhizomes of Veratrum dahuricum, and six compounds (Veratramine (1), jervine (2), germine (3), veramitaline (4), veratrosine (5) and cyclopamine (6)) from the ethanol extract were investigated in vitro. The 12 samples exhibited cytotoxic activity against human tumor cell lines A549, PANC-1, SW1990 and NCI-H249. Among these samples, CHCl(3) fraction, the total alkaloids, compounds 1 and 6 showed higher inhibitory activity, compound 3 selectively exhibited significant cytotoxicity to SW1990 and NCI-H249.

Hypotensive effect and toxicology of total alkaloids and veratramine from roots and rhizomes of Veratrum nigrum L. in spontaneously hypertensive rats.[Pubmed:18771011]

Pharmazie. 2008 Aug;63(8):606-10.

Total alkaloids (VTA) and Veratramine of Veratrum nigrum L. were tested for hypotensive effect using spontaneously hypertensive rats (SHR). Acute toxicities were also evaluated. There was a dose-dependent reduction in blood pressure and heart rate after a single ingestion (1.0 to 4.0 mg/kg, intragastric administration) of VTA. A single oral ingestion (0.56 to 2.24 mg/kg) of Veratramine, the major component of VTA, dose-dependently decreased blood pressure and heart rate, suggesting that Veratramine was involved in the hypotensive effect of VTA in SHR. The hypotensive effects of VTA and Veratramine are directly positively correlated with the dosage. Side effects were not obvious.

Description

Veratramine(NSC17821; NSC23880) is useful as a signal transduction inhibitor for treating tumors.

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