Hasubanonine

Hasubanonine

Names
Other names Hasubanonine
Identifiers
CAS Registry Number	1805-85-2
ChemSpider	390731 Y
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
Jmol-3D images	Image
PubChem	442246
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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