Aknadinine

Aknadinine
Names
Other names
4-demethylhasubanonine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C20H25NO5/c1-21-10-9-19-11-13(22)17(25-3)18(26-4)20(19,21)8-7-12-5-6-14(24-2)16(23)15(12)19/h5-6,23H,7-11H2,1-4H3/t19-,20+/m0/s1
    Key: XLWYWPDYNLZUJS-VQTJNVASSA-N
  • CN1CC[C@@]23[C@@]1(CCC4=C2C(=C(C=C4)OC)O)C(=C(C(=O)C3)OC)OC
Properties
C20H25NO5
Molar mass 359.42
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Aknadinine (also known as 4-demethylhasubanonine) is an opioid alkaloid isolated from members of the genus Stephania (Stephania cepharantha and Stephania hernandifolia.). Structurally it is a member of the hasubanan family of alkaloids and features an isoquinoline substructure.

See also

References

  1. 1 2 Moza, B.K.; B. Bhaburi; D.K. Basu; J. Kunitomo; Y. Okamoto; E. Yuge; Y. Nagai; T. Ibuka (1970). "Constitution of three new alkaloids, aknadinine (4-demethylhasubanonine), aknadicine (4-demethylnorhasubanonine), and aknadilactam (4-demethyl-16-oxohasubanonine)". Tetrahedron. 26 (2): 427–433. doi:10.1016/S0040-4020(01)97839-1. ISSN 0040-4020.
  2. ↑ He, L; Zhang, YH; Tang, LJ; Song, SH; Sun, QY (October 2010). "[Study on the alkaloids in the stems and leaves of Stephania cepharantha (II)]". Zhong Yao Cai (in Chinese). 33 (10): 1568–1570. PMID 21355192.
  3. ↑ Kupchan, SM; Suffness, MI; White, DN; McPhail, AT; Sim, GA (1968). "The isolation and structural elucidation of 4-demethylhasubanonine, a new alkaloid from Stephania hernandifolia". Journal of Organic Chemistry. 33 (12): 4529–32. doi:10.1021/jo01276a052. PMID 5743784.