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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17N3O
Molecular Weight 303.3578
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EVODIAMINE

SMILES

[H][C@]12N(C)C3=C(C=CC=C3)C(=O)N1CCC4=C2NC5=CC=CC=C45

InChI

InChIKey=TXDUTHBFYKGSAH-SFHVURJKSA-N
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

HIDE SMILES / InChI

Description

Evodiamine, a naturally occurring indole alkaloid, is one of the main bioactive ingredients of Evodia Rutaecara, the dried unripe fruit of which is also known as Wu zhu yu (Wu Zhu Yu, interchangeably) or Evodia Fruit. Evodia Fruit used in Traditional Chinese Medicine for the purposes of warmth, intestinal comfort (specifically; to alleviate abdominal pain, acid regurgitation, nausea and diarrhea), dysmenorrheal, and fighting inflammation and infections. With respect to the pharmacological actions of evodiamine, more attention has been paid to beneficial effects in insults involving cancer, obesity, nociception, inflammation, cardiovascular diseases, Alzheimer's disease, infectious diseases and thermo-regulative effects. Evodiamine has evolved a superior ability to bind various proteins including TRPV1, the aryl hydrocarbon receptor (AhR), and topoisomerases I and II. There are currently no human studies on evodia rutaecarpa berries or evodiamine.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
60.74 µM [IC50]
78.81 µM [IC50]
5.95 µM [Ki]
28.4 nM [Ki]
5.0 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Evodiamine is an active component of Evodia Rutaecara, the dried unripe fruit of which is also known as Wu zhu yu (Wu Zhu Yu, interchangeably) or Evodia Fruit, is a herb used in Traditional Chinese Medicine at doses of 3-9 grams (of the berries) thrice a day for the purposes of warmth, intestinal comfort (specifically; to alleviate abdominal pain, acid regurgitation, nausea and diarrhea), dysmenorrheal, and fighting inflammation and infections. In addition evodiamine is main component of a number of dietary supplement wich may help to promote diuresis and fat metabolism and increase energy.
Route of Administration: Oral
In Vitro Use Guide
20-40 μM evodiamine treatment for 24-48 h strongly reduced the growth and survival of human lung cancer A549 and H1299 cells