Dicentrine

Last updated
Dicentrine
(S)-(+)-dicentrine.svg
Names
Preferred IUPAC name
(7aS)-10,11-Dimethoxy-7-methyl-6,7,7a,8-tetrahydro-2H,5H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinoline
Other names
(S)-(+)-Dicentrine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1
    Key: YJWBWQWUHVXPNC-AWEZNQCLSA-N
  • CN1CCc2cc3c(c-4c2[C@@H]1Cc5c4cc(c(c5)OC)OC)OCO3
Properties
C20H21NO4
Molar mass 339.391 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dicentrine is an aporphinic alkaloid found in several plant species, mainly from family Lauraceae, including Lindera megaphylla . [1] At high doses, dicentrine shows antinociceptive activity in a mouse model of pain. [2] It probably acts via a TRPA1-dependent mechanism. [2]

References

  1. ↑ Huang, Ray-Ling; Chen, Chien-Chih; Huang, Yu-Lin; Ou, Jun-Chih; Hu, Cheng-Po; Chen, Chieh-Fu; Chang, Chungming (1998). "Anti-Tumor Effects of d-Dicentrine from the Root of Lindera megaphylla". Planta Medica. 64 (3): 212–215. doi:10.1055/s-2006-957411. PMID   9581516.
  2. 1 2 Montrucchio, Deise Prehs; Córdova, Marina Machado; Santos, Adair Roberto Soares (2013-07-04). "Plant Derived Aporphinic Alkaloid S-(+)-Dicentrine Induces Antinociceptive Effect in Both Acute and Chronic Inflammatory Pain Models: Evidence for a Role of TRPA1 Channels". PLOS ONE. 8 (7) e67730. Bibcode:2013PLoSO...867730M. doi: 10.1371/journal.pone.0067730 . ISSN   1932-6203. PMC   3701576 . PMID   23861794.
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