Apparicine

Apparicine
Names
IUPAC name
(19E)-2,7,16,17,19,20-Hexadehydro-3,7-seco-6-norcuran
Systematic IUPAC name
(2R,4E,5S)-4-Ethylidene-6-methylidene-1,3,4,5,6,7-hexahydro-2,5-ethanoazocino[4,3-b]indole
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C18H20N2/c1-3-13-10-20-9-8-14(13)12(2)18-16(11-20)15-6-4-5-7-17(15)19-18/h3-7,14,19H,2,8-11H2,1H3/b13-3-/t14-/m1/s1
    Key: LCVACABZTLIWCE-CRAFIKPXSA-N
  • C\C=C1\C[N@]2CC[C@@H]1C(=C)c1[nH]c3ccccc3c1C2
Properties
C18H20N2
Molar mass 264.372 g·mol−1
Density 0.945875
log P 3.404
Acidity (pKa) 8.37
1.665
0.552121
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Apparicine is a monoterpenoid tricyclic indole alkaloid.[1] It is named after Apparicio Duarte, a Brazilian botanist who studied the Aspidosperma species from which apparicine was first isolated.[2][3] It was the first member of the vallesamine group of indole alkaloids to be isolated and have its structure established,[3] which was first published in 1965.[4] It has also been known by the synonyms gomezine, pericalline, and tabernoschizine.[5]

  1. ^ Herbert 1983, p. 13.
  2. ^ Elia 2008, p. 594.
  3. ^ a b Joule 1983, p. 286.
  4. ^ Joule et al. 1965, p. 4773.
  5. ^ Gilbert 1968, p. 273.