Evodiamine

Evodiamine
Clinical data
ATC code	none;
Identifiers
	IUPAC name 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	518-17-2 ;
PubChem CID	442088;
ChemSpider	133343 ;
UNII	C01825BVNL;
ChEMBL	ChEMBL486598 ;
CompTox Dashboard (EPA)	DTXSID10966123 ;
ECHA InfoCard	100.164.846
Chemical and physical data
Formula	C19H17N3O
Molar mass	303.365 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4N3CCc2c([nH]c1ccccc12)C3N(c5ccccc45)C;
	InChI 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 ; Key:TXDUTHBFYKGSAH-UHFFFAOYSA-N ;
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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.

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[Kobiyashi2001-1] 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.

[Wang2008-2] 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.

[3] 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.