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Chemical Structure| 67909-49-3 Chemical Structure| 67909-49-3

Structure of Dehydroevodiamine
CAS No.: 67909-49-3

Chemical Structure| 67909-49-3

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Dehydroevodiamine is an alkaloid isolated from E. rutaecarpa and possesses anti-inflammatory, antiarrhythmic, hypotensive, and anti-amnesic biological activities.

Synonyms: DHED

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Product Details of Dehydroevodiamine

CAS No. :67909-49-3
Formula : C19H15N3O
M.W : 301.34
SMILES Code : O=C1N2C(C([N-]C3=C4C=CC=C3)=C4CC2)=[N+](C)C5=C1C=CC=C5
Synonyms :
DHED
MDL No. :MFCD11656140
InChI Key :VXHNSVKJHXSKKM-UHFFFAOYSA-N
Pubchem ID :9817839

Safety of Dehydroevodiamine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280-P305+P351+P338

Related Pathways of Dehydroevodiamine

pyroptosis

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Hepa-1c1c7 cells 5 μM 12 h To confirm whether RUT, EOD, and DHED activate the AHR. Results showed that at 5 μM, RUT, EOD, and DHED induced luciferase activity by 23.6-, 2.14-, and 10.8-fold, respectively. Drug Metab Dispos. 2018 Jul;46(7):1030-1040
HepG2 cells 5 μM 12 h To confirm whether RUT, EOD, and DHED activate the AHR. Results showed that at 5 μM, RUT, EOD, and DHED induced luciferase activity by 20.4-, 2.43-, and 6.60-fold, respectively. Drug Metab Dispos. 2018 Jul;46(7):1030-1040
Mouse primary hepatocytes 5 μM 24 h To investigate whether RUT, EOD, and DHED could directly activate the AHR. Results showed that Cyp1a1 mRNA was significantly upregulated by RUT, EOD, and DHED, with induction of 665-, 12.5-, and 20.6-fold, respectively, with an efficacy order of RUT > DHED > EOD. Drug Metab Dispos. 2018 Jul;46(7):1030-1040

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
C57BL/6N mice Wild-type and Ahr-/- mice Gavage 80 mg/kg Once daily for 3, 12, and 21 days To determine whether RUT, EOD, and DHED possess AHR activity in vivo. Results showed that RUT and DHED significantly induced the expression of Cyp1a1, Cyp1a2, and Cyp1b1 mRNAs in Ahr+/+ mice but not in Ahr-/- mice. EOD failed to activate AHR in vivo. Additionally, RUT and DHED disrupted bile acid homeostasis via an AHR-dependent mechanism. Drug Metab Dispos. 2018 Jul;46(7):1030-1040
SD rats DSS-induced ulcerative colitis model Gavage 20 mg/kg and 40 mg/kg 7 consecutive days Significantly alleviated DSS-induced colitis symptoms, suppressed inflammatory and oxidative stress responses, repaired colonic barrier injury, inhibited apoptosis, modulated gut microbes and serum metabolites, and inhibited the PI3K/AKT/NF-κB signaling pathway by targeting AKT1 Molecules. 2024 Aug 26;29(17):4031

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.32mL

0.66mL

0.33mL

16.59mL

3.32mL

1.66mL

33.19mL

6.64mL

3.32mL

Dissolving Methods
The prepared working fluid is recommended to be prepared now and used up as soon as possible in a short period of time. The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

References

[1]Shin KY, Kim KY, Suh YH. Dehydroevodiamine·HCl enhances cognitive function in memory-impaired rat models. Korean J Physiol Pharmacol. 2017 Jan;21(1):55-64.

[2]Shin KY, Noh SJ, et al. Dehydroevodiamine•HCl Protects Against Memory Impairment and Cerebral Amyloid-β Production in Tg2576 Mice by Acting as a γ-Secretase Inhibitor. CNS Neurol Disord Drug Targets. 2016;15(8):935-944.

[3]Loh SH, Tsai YT, Lee CY, Chang CY, Tsai CS, Cheng TH, Lin CI. Antiarrhythmic effects of dehydroevodiamine in isolated human myocardium and cardiomyocytes. J Ethnopharmacol. 2014 May 14;153(3):753-62

[4]Noh EJ, Ahn KS, Shin EM, Jung SH, Kim YS. Inhibition of lipopolysaccharide-induced iNOS and COX-2 expression by dehydroevodiamine through suppression of NF-kappaB activation in RAW 264.7 macrophages. Life Sci. 2006 Jul 10;79(7):695-701

[5]Wang HH, Chou CJ, Liao JF, Chen CF. Dehydroevodiamine attenuates beta-amyloid peptide-induced amnesia in mice. Eur J Pharmacol. 2001 Feb 16;413(2-3):221-5

[6]Shin KY, Kim KY, Suh YH. Dehydroevodiamine•HCl enhances cognitive function in memory-impaired rat models. Korean J Physiol Pharmacol. 2017 Jan;21(1):55-64

[7]Peng JH, Zhang CE, Wei W, Hong XP, Pan XP, Wang JZ. Dehydroevodiamine attenuates tau hyperphosphorylation and spatial memory deficit induced by activation of glycogen synthase kinase-3 in rats. Neuropharmacology. 2007 Jun;52(7):1521-7

[8]Fang J, Liu R, Tian Q, Hong XP, Wang SH, Cao FY, Pan XP, Wang JZ. Dehydroevodiamine attenuates calyculin A-induced tau hyperphosphorylation in rat brain slices. Acta Pharmacol Sin. 2007 Nov;28(11):1717-23

 

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