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E3531

Sigma-Aldrich

Evodiamine

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About This Item

Empirical Formula (Hill Notation):
C19H17N3O
CAS Number:
518-17-2
Molecular Weight:
303.36
MDL number:
MFCD06407824
UNSPSC Code:
12352116
PubChem Substance ID:
329799050
NACRES:
NA.25

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

[H][C@@]1(N(C)C2=C3C=CC=C2)C4=C(C(C=CC=C5)=C5N4)CCN1C3=O

InChI

1S/C19H17N3O/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/h2-9,18,20H,10-11H2,1H3/t18-/m0/s1

InChI key

TXDUTHBFYKGSAH-SFHVURJKSA-N

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Biochem/physiol Actions

Evodiamine is an indole alkaloid found in Evodia rutaescarpa. It acts as an anti-inflammatory compound; the mechanism of action may be inhibition of prostaglandin E2 synthesis or by cyclooxygenase 2 induction and NF-κB activation. Evodiamine has been studied for multiple cellular effects, including apoptotic activity, interference with metastasis and inhibition of angiogenesis.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Wanbin Yang et al.
Investigational new drugs, 37(5), 865-875 (2018-11-30)
Purpose Transdifferentiation exists within stromal cells in the tumour microenvironment. Transforming growth factor-β (TGF-β) secreted by tumour-associated fibroblasts (TAFs) affects the differentiation states of epithelial cells, including epithelial-mesenchymal transition (EMT). Evodiamine, a natural drug, can regulate differentiation. However, the specific
Rui-fang Li et al.
Pharmacology, 97(1-2), 43-47 (2015-11-21)
The objective of this work was to investigate the effect of orally administered evodiamine on the pharmacokinetics of dapoxetine and its active metabolite desmethyl dapoxetine in rats. Twelve healthy male Sprague-Dawley rats were randomly divided into 2 groups: the control
Jia Du et al.
Anticancer research, 37(11), 6141-6151 (2017-10-25)
The synergistic combinations of natural products have long been the basis of Traditional Chinese herbal Medicine formulas. In this study, we investigated the synergistic effects of a combination of berberine and evodiamine against human breast cancer MCF-7 cells in vitro
Fan Yang et al.
Biochemical and biophysical research communications, 485(1), 54-61 (2017-02-13)
Evodiamine is an alkaloid extracted from Euodia rutaecarpa (Juss.) Benth. There is little information about the mechanisms of evodiamine on the apoptosis of hepatocellular carcinoma (HCC). A xenograft model and CCK8 assay were used to investigate the anti-HCC effect of
Yang-Ling Li et al.
Biochemical and biophysical research communications, 498(3), 481-486 (2018-03-06)
Hypoxia promotes HCC progression and therapy resistance, and there is no systemic treatment for HCC patients after sorafenib resistance. Thus, it is urgent to develop potential therapeutic regimens for HCC patients by targeting hypoxia signaling. In this study, we showed
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Articles

NF-κB and Inflammation

Chronic inflammation is an underlying factor in the development and progression of many of the chronic diseases of aging, such as arthritis, atherosclerosis, diabetes, and cancer.

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