Evoxine

Evoxine (haploperine) is a furoquinoline alkaloid with hypnotic and sedative effects. It is found naturally in a variety of Australian and African plants including Evodia xanthoxyloides[1] and Teclea gerrardii.[2]

Evoxine
Names
IUPAC name
(±)-1-(4,8-Dimethoxyfuro[2,3-b]quinolin-7-yl)oxy-3-methylbutane-2,3-diol
Other names
Haploperine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
InChI
  • InChI=1S/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
    Key: FGANMDNHTVJAHL-UHFFFAOYSA-N
  • InChI=1/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
    Key: FGANMDNHTVJAHL-UHFFFAOYAV
SMILES
  • CC(C)(C(COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC)O)O
Properties
Chemical formula
 C18H21NO6
Molar mass 347.367 g·mol−1
Pharmacology
none
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Eastwood, FW; Hughes, GK; Ritchie, E. (1954). "Alkaloids of the Australian Rutaceae: Evodia xanthoxyloides F.Muell. IV. The structures of Evoxine and Evoxoidine". Australian Journal of Chemistry. 7 (1): 87–98. doi:10.1071/CH9540087.
  2. Waffo, AF; Coombes, PH; Crouch, NR; Mulholland, DA; El Amin, SM; Smith, PJ (2007). "Acridone and furoquinoline alkaloids from Teclea gerrardii (Rutaceae: Toddalioideae) of southern Africa". Phytochemistry. 68 (5): 663–7. doi:10.1016/j.phytochem.2006.10.011. PMID 17174364.


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