Gigantine

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Gigantine
Gigantine v2.svg
Names
IUPAC name
6,7-dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-5-ol
Other names
1,2-Dimethyl-5-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
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
    Key: HRJQUAXWKYISJC-UHFFFAOYSA-N
  • 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
  • CC1C2=CC(=C(C(=C2CCN1C)O)OC)OC
  • C[C@H]1C=2C(=C(O)C(OC)=C(OC)C2)CCN1C
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).

Gigantine is a tetrahydroisoquinoline alkaloid found in Carnegiea gigantea and other related cactus species. [1] [2] It was first discovered along with macromerine in 1967. [3] Gigantine is found in significant quantities in many mescaline-containing cactus species, but it is unclear whether it contributes to their psychoactive effects. [1] The compound has been suspected to be hallucinogenic based on animal studies in cats and monkeys, but has not been evaluated in humans. [4] [3]

Contents

See also

References

  1. 1 2 Shulgin, Alexander Theodore; Perry, Wendy E. (2002). The Simple Plant Isoquinolines. Transform Press. ISBN   978-0-9630096-2-3. OCLC   51006569. OL   8521520M.
  2. ↑ Bruhn JG, Lundström J (1976). "Alkaloids of Carnegiea gigantea. Arizonine, a new tetrahydroisoquinoline alkaloid". Lloydia. 39 (4): 197–203. PMID   957908.
  3. 1 2 Hodgkins JE, Brown SD, Massingill JL (April 1967). "Two new alkaloids in cacti". Tetrahedron Lett. 8 (14): 1321–1324. doi:10.1016/s0040-4039(00)90694-4. PMID   6044211. Synthetic d,l-macromerine, natural macromerine and natural gigantine are physiologically active. Both alkaloids caused hallucinogenic reactions when tested on squirrel monkeys and cats (macromerine; 20 mg/kilo-I.P., hallucinogenic; gigantine, 20 mg/kilo-I.P., lethal; 5 mg/kilo-I.P., hallucinogenic).14 Macromerine shows "anti" adrenaline results in the turtle heart.15 [...] REFERENCES [...] (14) We wish to thank Dr. E. S. Barratt, Director, Behavioral Science Lab., Department of Neurology and Psychiatry, University of Texas Medical Branch, Galveston, Texas, for obtaining the physiological data. (15) We wish to thank S. Eppstein, M.D., for his interpretation of the E.K.G.'s and Professor E. W. Gardner of T.C.U. for assistance in obtaining the [...]
  4. ↑ Keeper Trout & friends (2013). Trout's Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1) (PDF). Mydriatic Productions/Better Days Publishing. Suspected hallucinogen based on animal studies. Claimed to be hallucinogenic in monkeys and cats at 5 mg./ kg./ip.; Hodgkins et al. 1967. Apparently lacking any human evaluation. Fatal in monkeys and cats at 20 mg/kg/ip. Hodgkins et al. 1967.


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