Evodiamine

Title: Evodiamine
CAS Registry Number: 518-17-2
CAS Name: 8,13,13b,14-Tetrahydro-14-methylindolo[2¢,3¢:3,4]pyrido[2,1-b]quinazolin-5(7H)-one
Molecular Formula: C19H17N3O
Molecular Weight: 303.36
Percent Composition: C 75.23%, H 5.65%, N 13.85%, O 5.27%
Literature References: From Evodia rutaecarpa Hook. & Thoms and bark of Zanthoxylum rhetsa DC., Rutaceae: Y. Asahina, K. Kashiwaki, J. Pharm. Soc. Jpn. 1915, 1293, C.A. 10, 607 (1916); Gopinath et al., Tetrahedron 8, 293 (1960). Structure: Y. Asahina J. Pharm. Soc. Jpn. 1924, 1; Ohta, J. Pharm. Soc. Jpn. 65, 15 (1945), C.A. 45, 5697 (1951). Synthesis: Asahina, Ohta, Ber. 61B, 319 (1928); T. Kametani et al., J. Am. Chem. Soc. 98, 6186 (1976); eidem, Heterocycles 4, 23 (1976). Biosynthesis: M. Yamazaki et al., Tetrahedron Lett. 1966, 3221; 1967, 3317. Mass spec.: J. Tamas et al., Acta Chim. Acad. Sci. Hung. 89, 85 (1976).
Properties: Yellow plates from alc, mp 278°. [a]D15 +352° (acetone); [a]D +440° (chloroform). uv max (acetonitrile): 272, 280, 291, 335 nm (log e 4.06, 4.02, 3.90, 3.30). Sol in acetone; slightly sol in alcohol, ether, chloroform. Practically insol in water, petr ether, benzene. Does not seem to form salts.
Melting point: mp 278°
Optical Rotation: [a]D15 +352° (acetone); [a]D +440° (chloroform)
Absorption maximum: uv max (acetonitrile): 272, 280, 291, 335 nm (log e 4.06, 4.02, 3.90, 3.30)
Exalamide Exaltolide? Exemestane Exendins Exifone

Evodiamine
Skeletal formula
Space-filling model
Systematic (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
Clinical data
Legal status  ?
Identifiers
CAS number 518-17-2 YesY
ATC code None
PubChem CID 151289
ChemSpider 133343 YesY
ChEMBL CHEMBL486598 N
Chemical data
Formula C19H17N3O 
Mol. mass 303.36 g/mol
 N (what is this?)  (verify)

Evodiamine is a chemical extracted from the Tetradium family of plants, 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 in a manner comparable to tianeptine by increasing the number of serotonin transporters available in the brain, enhacing the reuptake of serotonin.[3]