Muldamine
Stereo skeletal formula of muldamine
Ball-and-stick model of muldamine
Names
IUPAC name
3β-Hydroxy-16,28-seco-22β-solanid-5-en-16α-yl acetate
Systematic IUPAC name
(1R,2R,3aS,3bS,7S,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-1-{(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl}-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl acetate
Other names
Alkaloid Q

Teinemine 16-acetate

5-Veratranine-3β,11α-diol 11-acetate
Identifiers
3D model (JSmol)
ChemSpider
MeSH Muldamine
UNII
  • InChI=1S/C29H47NO3/c1-17-6-9-25(30-16-17)18(2)27-26(33-19(3)31)15-24-22-8-7-20-14-21(32)10-12-28(20,4)23(22)11-13-29(24,27)5/h7,17-18,21-27,30,32H,6,8-16H2,1-5H3 checkY
    Key: ZVYUDNWAHWVPPN-UHFFFAOYSA-N checkY
  • CC(C1C(CC2C3CC=C4CC(O)CCC4(C)C3CCC12C)OC(C)=O)C1CCC(C)CN1
Properties
C29H47NO3
Molar mass 457.699 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Muldamine is a phytosterol alkaloid isolated from Veratrum californicum.[1] It is the acetate ester of the piperidine steroid teinemine.[2]

See also

References

  1. ↑ Keeler R F (1971). "Teratogenic compounds of Veratrum californicum (Durand). 13. Structure of muldamine". Steroids. 18 (6): 741–752. doi:10.1016/0039-128X(71)90033-X. PMID 5135731.
  2. ↑ Gaffield, William; Wong, Rosalind Y.; Lundin, Robert E.; Keeler, Richard F. (1982). "Structure of the steroidal alkaloid muldamine and its deacetyl derivative". Phytochemistry. 21 (9): 2397–2400. Bibcode:1982PChem..21.2397G. doi:10.1016/0031-9422(82)85214-X. S2CID 84867178.


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