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Hasubanonine

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Hasubanonine
Names
Systematic IUPAC name 3,4,7,8-Tetramethoxy-17-methyl-7,8-didehydrohasubanan-6-one
Other names Hasubanonine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C21H27NO5/c1-22-11-10-20-12-14(23)17(25-3)19(27-5)21(20,22)9-8-13-6-7-15(24-2)18(26-4)16(13)20/h6-7H,8-12H2,1-5H3/t20-,21+/m0/s1Key: DXUSNRCTWFHYFS-LEWJYISDSA-N
  • InChI=1/C21H27NO5/c1-22-11-10-20-12-14(23)17(25-3)19(27-5)21(20,22)9-8-13-6-7-15(24-2)18(26-4)16(13)20/h6-7H,8-12H2,1-5H3/t20-,21+/m0/s1Key: DXUSNRCTWFHYFS-LEWJYISDBB
SMILES
  • O=C4C(\OC)=C(\OC)23N(CC3(c1c(ccc(OC)c1OC)CC2)C4)C
Properties
Chemical formula C21H27NO5
Molar mass 373.449 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Hasubanonine is a member of the hasubanan family of alkaloids. The alkaloid with an isoquinoline substructure has the molecular formula of C21H27NO5. The enantiomer of the natural product is being studied as a potential painkiller. Hasubanonine is structurally related to the morphinan class of opioid analgesics.

The enantioselective total synthesis of (–)-hasubanonine and related natural products, (−)-runanine, (−)-delavayine, and (+)-periglaucine B were first achieved by Prof. Seth Herzon and co-workers at Yale University in 2011.

References

  1. Hasubanonine
  2. "Y. Chemists hoping to ease pain". Deseret News. August 17, 2006. Archived from the original on March 10, 2007.
  3. Herzon, Seth B.; Calandra, Nicholas A.; King, Sandra M.; McCarthy, M. C.; Gauss, J. (2011). "Efficient Entry to the Hasubanan Alkaloids: First Enantioselective Total Syntheses of (−)-Hasubanonine, (−)-Runanine, (−)-Delavayine, and (+)-Periglaucine B". Angewandte Chemie International Edition. 50 (38): 8863–8866. doi:10.1002/anie.201102226. PMID 21638524.


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