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Chemical compound
Evodiamine
ATC code
21-Methyl-3,13,21-triazapentacyclo[11.8.0.02,10 .04,9 .015,20 ]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
CAS Number
PubChem
CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.164.846
Formula C 19 H 17 N 3 O
Molar mass 303.365 g·mol−1 3D model (
JSmol )
O=C4N3CCc2c([nH]c1ccccc12)C3N(c5ccccc45)C
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
Y Key:TXDUTHBFYKGSAH-UHFFFAOYSA-N
Y
N Y
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Evodiamine is a
chemical compound extracted from the plant genus
Tetradium , which has been shown to reduce fat uptake in mouse studies. It is suspected that its
mechanism of action is similar to that of
capsaicin .
[1] As such, it has been included in some dietary supplements. Neither its fat-burning effects in humans nor any potential side effects have been empirically established.
Evodiamine acts primarily as a
thermogenic and
stimulant .
[2]
Evodiamine may also act by increasing the number of
serotonin transporters available in the brain, enhancing the reuptake of serotonin.
[3]
References
^ Kobayashi Y, Nakano Y, Kizaki M, Hoshikuma K, Yokoo Y, Kamiya T (October 2001). "Capsaicin-like anti-obese activities of evodiamine from fruits of Evodia rutaecarpa, a vanilloid receptor agonist". Planta Medica . 67 (7): 628–33.
doi :
10.1055/s-2001-17353 .
PMID
11582540 .
S2CID
19937385 .
^ Wang T, Wang Y, Kontani Y, Kobayashi Y, Sato Y, Mori N, Yamashita H (January 2008).
"Evodiamine improves diet-induced obesity in a uncoupling protein-1-independent manner: involvement of antiadipogenic mechanism and extracellularly regulated kinase/mitogen-activated protein kinase signaling" . Endocrinology . 149 (1): 358–66.
doi :
10.1210/en.2007-0467 .
PMID
17884939 .
^ Hu Y, Ehli EA, Hudziak JJ, Davies GE (October 2012). "Berberine and evodiamine influence serotonin transporter (5-HTT) expression via the 5-HTT-linked polymorphic region". The Pharmacogenomics Journal . 12 (5): 372–8.
doi :
10.1038/tpj.2011.24 .
PMID
21647174 .
S2CID
11148104 .
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14 -prostaglandin J2
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ginger ,
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ginger ,
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garlic )
AM404
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chili pepper )
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oregano ,
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wild bergamot , others)
DHEA
Diacyl glycerol
Dihydrocapsaicin (
chili pepper )
Estradiol
Eugenol (
basil ,
clove )
Evodiamine (
Euodia ruticarpa )
Gingerols (
ginger )
GSK1016790A
Heat
Hepoxilin A3
Hepoxilin B3
Homocapsaicin (
chili pepper )
Homodihydrocapsaicin (
chili pepper )
Incensole (
incense )
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pH (acidic conditions)
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Ruta graveolens )
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Euphorbia resinifera /
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Euphorbia resinifera /
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