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| 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 | |
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| Properties | |
| C13H19NO3 | |
| Molar mass | 237.299 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Gigantine is atetrahydroisoquinolinealkaloid found inCarnegiea gigantea and other relatedcactus species.[1][2] It was first discovered along withmacromerine in 1967.[3] Gigantine is found in significant quantities in manymescaline-containing cactus species, but it is unclear whether it contributes to theirpsychoactive effects.[1] The compound has been suspected to behallucinogenic based on animal studies in cats and monkeys, but has not been evaluated in humans.[4][3]
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 [...]
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.
