Hasubanan is an alkaloid with the chemical formula of C16H21N. It forms the central core of a class of alkaloids known collectively as hasubanans.[1] The compound is derived from reticuline, as is morphinan, but is comparatively more oxidized and rearranged. It is similar to acutumine.

Hasubanan
Names
IUPAC name
(3aS-cis)-2,3,4,5-Tetrahydro-3a,9b-butano-1H-benz[e]indole
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C16H21N/c1-2-6-14-13(5-1)7-10-16-9-4-3-8-15(14,16)11-12-17-16/h1-2,5-6,17H,3-4,7-12H2/t15-,16+/m1/s1 checkY
    Key: RKWPQIQYRNOTMT-CVEARBPZSA-N checkY
  • InChI=1/C16H21N/c1-2-6-14-13(5-1)7-10-16-9-4-3-8-15(14,16)11-12-17-16/h1-2,5-6,17H,3-4,7-12H2/t15-,16+/m1/s1
    Key: RKWPQIQYRNOTMT-CVEARBPZBP
  • C2C[C@]14CCCC[C@@]4(CCN1)c3ccccc23
Properties
C16H21N
Molar mass 227.351 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Various alkaloids of this family have been synthesized in the laboratories.[2]

See also

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References

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  1. ^ Zhang H, Yue J (2005). "Hasubanan type alkaloids from Stephania longa". J Nat Prod. 68 (8): 1201–7. doi:10.1021/np0500833. PMID 16124761.
  2. ^ Ikonnikova, Viktoria A.; Baranov, Mikhail S.; Mikhaylov, Andrey A. (2022-07-18). "Developments in the Synthesis of Hasubanan Alkaloids". European Journal of Organic Chemistry. 2022 (31): ejoc.202200675. doi:10.1002/ejoc.202200675. ISSN 1434-193X. S2CID 250661115.
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