Evodiamine (CAS 518-17-2)

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Application:	An antiangiogenic and antiinflammatory agonist of TRPV1
CAS Number:	518-17-2
Purity:	97%
Molecular Weight:	303.4
Molecular Formula:	C₁₉H₁₇N₃O

Ordering Information

Product Name	Catalog #	Unit	Price	Qty	Add
Evodiamine	sc-201479	20 mg	$26
Evodiamine	sc-201479A	100 mg	$70

This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.

Description

Evodiamine is a quinozole alkaloid isolated from Evodia rutaecarpa, described as an agonist of the vanilloid receptor subtype 1 (TRPV1) with affinity (K_i = 5.95 microM) comparable to that of the prototypical TRPV1 chemical activator Capsaicin (sc-3577, K_i= 1.8 microM). Evodiamine induction of ⁴⁵Ca²⁺ uptake was competitively antagonized by the Capsaicin antagonist Capsazepine (sc-201098). Evodiamine is described to inhibit prostaglandin E₂ synthesis, cyclooxygenase-2 induction and NF-κB activation, producing antiinflammatory effects. The interferon-γ priming signal regulating the transcriptional activation of the iNOS gene is blocked by Evodiamine, suppressing iNOS protein synthesis but not affecting iNOS function. Evodiamine also demonstrates antiangiogenesis through inhibition of vascular endothelial growth factor gene expression and inhibition of the p44/p42 mitogen-activated protein kinase that correlated to endothelial cell angiogenesis. Promotion of apoptosis in human leukemic U937 cells is described with Evodiamine.

Technical Information

Appearance:	Off-white to light yellow solid
Physical State:	Solid
Derived from:	Evodia rutaecarpa
Solubility:	Soluble in DMSO (5 mg/mL,warm to 40°C), water (<1 mg/mL) at 25 °C, and ethanol (<1 mg/mL) at 25 °C.
Storage:	Store at -20° C
Melting Point:	278 °C
Boiling Point:	575.07 °C at 760 mmHg (Predicted)
Density:	1.40 g/cm³ (Predicted)
Refractive Index:	n²⁰_D 1.76 (Predicted)
Ki Data:	TRPV1: K_i= 5.95 µM (rat)

Safety and Reference Information

Transport:	UN 2811, Class 6.1, Packing group III
WGK Germany:	3
PubChem CID:	151289
Merck Index:	14: 3908
MDL Number:	MFCD06407824
SMILES:	CN1C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

References

1. Chiou, W.F., et al. 1997. J. Nat. Prod. 60: 708-711. PMID: 9249975
2. Pearce, L.V., et al. 2004. Org. Biomol. Chem. 2: 2281-2286. PMID: 15305207
3. Choi, Y.H., et al. 2006. Arch. Pharm. Res. 29: 293-297. PMID: 16681034
4. Shyu, K.G., et al. 2006. Life Sci. 78: 2234-2243. PMID: 16280136
5. Lee, T.J., et al. 2006. Mol. Cancer Ther. 5: 2398-2407. PMID: 16985074

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