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Dehydroevodiamine

CAS# 67909-49-3

Dehydroevodiamine

2D Structure

Catalog No. BCN2974----Order now to get a substantial discount!

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Dehydroevodiamine

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Chemical Properties of Dehydroevodiamine

Cas No. 67909-49-3 SDF Download SDF
PubChem ID 9817839 Appearance Yellow powder
Formula C19H15N3O M.Wt 301.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1,3,5,7,9,15,17,19-octaen-14-one
SMILES CN1C2=CC=CC=C2C(=O)N3C1=C4C(=C5C=CC=CC5=N4)CC3
Standard InChIKey VXHNSVKJHXSKKM-UHFFFAOYSA-N
Standard InChI InChI=1S/C19H15N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9H,10-11H2,1H3
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 Dehydroevodiamine

The fruits of Evodia rutaecarpa

Biological Activity of Dehydroevodiamine

DescriptionDehydroevodiamine has anticholinesterase activity and an anti-amnesic effect, it also may be a novel and effective ligand for improvement of beta-amyloid type amnesia. Dehydroevodiamine has antiarrhythmic, and anti-inflammatory properties, the effect of dehydroevodiamine-mediated inhibition of the expression LPS-induced iNOS and COX-2 genes is due to under the suppression of NF-kappaB activation in the transcriptional level.
TargetsBeta Amyloid | NOS | COX | PGE | NF-kB
In vitro

Antiarrhythmic effects of dehydroevodiamine in isolated human myocardium and cardiomyocytes.[Pubmed: 24680993 ]

J Ethnopharmacol. 2014 May 14;153(3):753-62.

Dehydroevodiamine alkaloid (DeHE), a bioactive component of the Chinese herbal medicine Wu-Chu-Yu (Evodiae frutus), exerted antiarrhythmic effect in guinea-pig ventricular myocytes. We further characterize the electromechanical effects of DeHE in the human atrial and ventricular tissues obtained from hearts of patients undergoing corrective cardiac surgery or heart transplantation.
METHODS AND RESULTS:
The transmembrane potentials of human myocardia were recorded with a traditional microelectrode technique while sarcolemmal Na(+) and Ca(2+) currents in single human cardiomyocytes were measured by a whole-cell patch-clamp technique. The intracellular pH (pHi) and Na(+)-H(+) exchanger (NHE) activity were determined using BCECF-fluorescence in human atria. In human atria, DeHE (0.1-0.3 μM) depressed upstroke velocity, amplitude of action potential, and contractile force, both in slow and fast response action potential. Moreover, the similar depressant effects of DeHE were found in human ventricular myocardium. Both in isolated human atrial and ventricular myocytes, DeHE (0.1-1 μM) reversibly, concentration-dependently decreased the Na(+) and Ca(2+)currents. Moreover, DeHE (0.1 and 0.3 μM) suppressed delayed afterdepolarizations and aftercontractions, induced by epinephrine and high [Ca(2+)]o in atria. In human ventricular myocardium, the strophanthidin-induced triggered activities were attenuated by pretreating DeHE (0.3 μM). The resting pHi and NHE activity were also significantly increased by DeHE (0.1-0.3 μM).
CONCLUSIONS:
We concluded for the first time that, in the human hearts, DeHE could antagonize triggered arrhythmias induced by cardiotonic agents through a general reduction of the Na(+) and Ca(2+) inward currents, while increase of resting pHi and NHE activity.

In vivo

Dehydroevodiamine attenuates beta-amyloid peptide-induced amnesia in mice.[Pubmed: 11226396]

Eur J Pharmacol. 2001 Feb 16;413(2-3):221-5.

Dehydroevodiamine has been reported to have anticholinesterase activity and an anti-amnesic effect.
METHODS AND RESULTS:
This study examined the effects of Dehydroevodiamine on scopolamine- and beta-amyloid peptide-(25--35)-induced amnesia in mice, using a step-through passive avoidance test. Similarly to the cholinesterase inhibitor, physostigmine (0.03--0.3 mg/kg, i.p.), Dehydroevodiamine (0.75--12.0 mg/kg, i.p.) administered 30 min before the training trial, immediately after the training trial, and 30 min before the retention test significantly improved scopolamine- and beta-amyloid peptide-(25--35)-induced amnesia. In beta-amyloid peptide-(25--35)-induced amnesia, the rank order of anti-amnesic potency in these three administration schedules for Dehydroevodiamine was different from that for physostigmine. Furthermore, Dehydroevodiamine was more potent to improve beta-amyloid peptide-(25--35)-induced amnesia than scopolamine-induced amnesia when administered before the training trial.
CONCLUSIONS:
These results suggested that Dehydroevodiamine may have an action other than that of an anticholinesterase and may be a novel and effective ligand for improvement of beta-amyloid type amnesia.

Protocol of Dehydroevodiamine

Cell Research

Inhibition of lipopolysaccharide-induced iNOS and COX-2 expression by dehydroevodiamine through suppression of NF-kappaB activation in RAW 264.7 macrophages.[Pubmed: 16554073 ]

Life Sci. 2006 Jul 10;79(7):695-701.

Dehydroevodiamine is a major bioactive quinazoline alkaloid isolated from Evodiae Fructus.
METHODS AND RESULTS:
We investigated the anti-inflammatory properties of Dehydroevodiamine in RAW 264.7 murine macrophages. The results indicated that Dehydroevodiamine inhibited the expression of LPS-induced iNOS and COX-2 proteins and suppressed also their mRNAs from RT-PCR experiment on RAW 264.7 cells. Furthermore, this compound inhibited the level of LPS-stimulated prostaglandin E2 (PGE2) and LPS-induced nuclear factor-kappa B (NF-kappaB).
CONCLUSIONS:
Therefore, we suggested that the effect of Dehydroevodiamine-mediated inhibition of the expression LPS-induced iNOS and COX-2 genes is due to under the suppression of NF-kappaB activation in the transcriptional level.

Dehydroevodiamine Dilution Calculator

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Preparing Stock Solutions of Dehydroevodiamine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3179 mL 16.5893 mL 33.1785 mL 66.357 mL 82.9463 mL
5 mM 0.6636 mL 3.3179 mL 6.6357 mL 13.2714 mL 16.5893 mL
10 mM 0.3318 mL 1.6589 mL 3.3179 mL 6.6357 mL 8.2946 mL
50 mM 0.0664 mL 0.3318 mL 0.6636 mL 1.3271 mL 1.6589 mL
100 mM 0.0332 mL 0.1659 mL 0.3318 mL 0.6636 mL 0.8295 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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References on Dehydroevodiamine

Antiarrhythmic effects of dehydroevodiamine in isolated human myocardium and cardiomyocytes.[Pubmed:24680993]

J Ethnopharmacol. 2014 May 14;153(3):753-62.

ETHNOPHARMACOLOGICAL RELEVANCE: Dehydroevodiamine alkaloid (DeHE), a bioactive component of the Chinese herbal medicine Wu-Chu-Yu (Evodiae frutus), exerted antiarrhythmic effect in guinea-pig ventricular myocytes. We further characterize the electromechanical effects of DeHE in the human atrial and ventricular tissues obtained from hearts of patients undergoing corrective cardiac surgery or heart transplantation. MATERIALS AND METHODS: The transmembrane potentials of human myocardia were recorded with a traditional microelectrode technique while sarcolemmal Na(+) and Ca(2+) currents in single human cardiomyocytes were measured by a whole-cell patch-clamp technique. The intracellular pH (pHi) and Na(+)-H(+) exchanger (NHE) activity were determined using BCECF-fluorescence in human atria. RESULTS: In human atria, DeHE (0.1-0.3 muM) depressed upstroke velocity, amplitude of action potential, and contractile force, both in slow and fast response action potential. Moreover, the similar depressant effects of DeHE were found in human ventricular myocardium. Both in isolated human atrial and ventricular myocytes, DeHE (0.1-1 muM) reversibly, concentration-dependently decreased the Na(+) and Ca(2+)currents. Moreover, DeHE (0.1 and 0.3 muM) suppressed delayed afterdepolarizations and aftercontractions, induced by epinephrine and high [Ca(2+)]o in atria. In human ventricular myocardium, the strophanthidin-induced triggered activities were attenuated by pretreating DeHE (0.3 muM). The resting pHi and NHE activity were also significantly increased by DeHE (0.1-0.3 muM). CONCLUSIONS: We concluded for the first time that, in the human hearts, DeHE could antagonize triggered arrhythmias induced by cardiotonic agents through a general reduction of the Na(+) and Ca(2+) inward currents, while increase of resting pHi and NHE activity.

Inhibition of lipopolysaccharide-induced iNOS and COX-2 expression by dehydroevodiamine through suppression of NF-kappaB activation in RAW 264.7 macrophages.[Pubmed:16554073]

Life Sci. 2006 Jul 10;79(7):695-701.

Dehydroevodiamine is a major bioactive quinazoline alkaloid isolated from Evodiae Fructus. We investigated the anti-inflammatory properties of Dehydroevodiamine in RAW 264.7 murine macrophages. The results indicated that Dehydroevodiamine inhibited the expression of LPS-induced iNOS and COX-2 proteins and suppressed also their mRNAs from RT-PCR experiment on RAW 264.7 cells. Furthermore, this compound inhibited the level of LPS-stimulated prostaglandin E2 (PGE2) and LPS-induced nuclear factor-kappa B (NF-kappaB). Therefore, we suggested that the effect of Dehydroevodiamine-mediated inhibition of the expression LPS-induced iNOS and COX-2 genes is due to under the suppression of NF-kappaB activation in the transcriptional level.

Description

Dehydroevodiamine is a major bioactive quinazoline alkaloid isolated from Evodiae Fructus, has an antiarrhythmic effect in guinea-pig ventricular myocytes. Dehydroevodiamine inhibits LPS-induced iNOS, COX-2, prostaglandin E2 (PGE2) and nuclear factor-kappa B (NF-κB) expression in murine macrophage cells.

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