Gigantine

Gigantine
Names
	Preferred IUPAC name (1S)-6,7-Dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-ol
Identifiers
CAS Number	32829-58-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	390724 ;
PubChem CID	442237;
UNII	5QO2DDT36D ;
	InChI 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 Key: HRJQUAXWKYISJC-QMMMGPOBSA-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;
	SMILES O(c1cc2c(c(O)c1OC)CCN(C)[C@H]2C)C;
Properties
Chemical formula	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

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]

References

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

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[pmid957908-1] 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