Crinine

Chemical compound From Wikipedia, the free encyclopedia

Crinine in an alkaloid found in a variety of plants including many species in the family Amaryllidaceae. It was first isolated and characterized in the 1950s as a constituent of several plants in the genus Crinum, from which it derives its name.[1][2][3]

Quick facts Names, Identifiers ...
Crinine
Names
IUPAC name
(1S,13R,15R)-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-15-ol
Other names
Crinidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2/t11-,15+,16+/m0/s1
    Key: RPAORVSEYNOMBR-IUIKQTSFSA-N
  • C1CN2CC3=CC4=C(C=C3[C@]15[C@H]2C[C@H](C=C5)O)OCO4
Properties
C16H17NO3
Molar mass 271.316 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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Several laboratory syntheses of crinine have been reported.[4][5][6][7]

There are many alkaloids with a chemical structure similar to crinine and they are generally referred to as crinine-type alkaloids. As of 2020, there were at least 85 known crinine-type alkaloids.[8]

Chemical structures of selected crinine-type alkaloids
Buphasine
Macowine
Augustisine
Amaryllisine
Buphanidrine

References

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