Gigantine

Gigantine
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
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]

See also

References

  1. ^ a b 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. ^ a b 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.


Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.