Gigantine

Gigantine is an tetrahydroisoquinoline alkaloid found in Carnegiea gigantea and other related cacti.[1] Gigantine was first discovered along with macromerine in 1967.[2] It is found in significant quantities in many mescaline-containing cactus species, but it is unclear whether gigantine contributes in any way to their psychoactive effects.[3]

Gigantine
Names
Preferred IUPAC name
(1S)-6,7-Dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H19NO3/c1-8-10-7-11(16-3)13(17-4)12(15)9(10)5-6-14(8)2/h7-8,15H,5-6H2,1-4H3/t8-/m0/s1 ☒N
    Key: HRJQUAXWKYISJC-QMMMGPOBSA-N ☒N
  • InChI=1/C13H19NO3/c1-8-10-7-11(16-3)13(17-4)12(15)9(10)5-6-14(8)2/h7-8,15H,5-6H2,1-4H3/t8-/m0/s1
    Key: HRJQUAXWKYISJC-QMMMGPOBBT
  • O(c1cc2c(c(O)c1OC)CCN(C)[C@H]2C)C
Properties
C13H19NO3
Molar mass 237.299 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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Infobox references

References
  1. Bruhn JG, Lundström J (1976). "Alkaloids of Carnegiea gigantea. Arizonine, a new tetrahydroisoquinoline alkaloid". Lloydia. 39 (4): 197–203. PMID 957908.
  2. "Two New Alkaloids in Cacti" [macromerine and gigantine] J E Hodgkins, Tetrahedron Lett., 14, 1321 (1967)
  3. Shulgin AT, Perry WE. The Simple Plant Isoquinolines. Transform Press, 2002. ISBN 978-0-9630096-2-3
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