Hasubanonine

Hasubanonine
Names

Other names Hasubanonine
Identifiers
CAS Number	1805-85-2^Y
3D model (Jmol)	Interactive image
ChemSpider	390731^Y
PubChem	442246
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/s1^Y Key: DXUSNRCTWFHYFS-LEWJYISDSA-N^Y 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/s1 Key: DXUSNRCTWFHYFS-LEWJYISDBB
SMILES O=C4C(\OC)=C(\OC)[C@]23N(CC[C@@]3(c1c(ccc(OC)c1OC)CC2)C4)C
Properties
Chemical formula	C₂₁H₂₇NO₅
Molar mass	373.19 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Hasubanonine is a member of the hasubanan family of alkaloids. The alkaloid with an isoquinoline substructure has the molecular formula of C₂₁H₂₇NO₅.^[1] The enantiomer of the natural product is being studied as a potential painkiller.^[2] 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. ^[3]

References

↑ Hasubanonine
↑ Deseret News - Chemists hoping to ease pain
↑ Herzon, S. B.; Calandra, N. A.; King, S. M. Angew. Chem. Int. Ed. 2011, 1:5 (12 September 2011), doi:10.1002/anie.201102226

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