Gramine
Chemical structure of gramine
Names
Preferred IUPAC name
1-(1H-Indol-3-yl)-N,N-dimethylmethanamine
Other names
donaxine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.591
EC Number
  • 201-749-8
KEGG
UNII
  • InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 checkY
    Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N checkY
  • InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
    Key: OCDGBSUVYYVKQZ-UHFFFAOYAK
  • c1cccc2c1c(c[nH]2)CN(C)C
Properties
C11H14N2
Molar mass 174.24 g/mol
Melting point 138 to 139 °C (280 to 282 °F; 411 to 412 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
1
0
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

Gramine (also called donaxine) is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.[1]

Occurrence

Gramine has been found in the giant reed, Arundo donax,[2][3] Acer saccharinum (Silver Maple),[4] Hordeum,[1][3] (a grass genus that includes barley) and Phalaris[3] (another grass genus).

Effects and toxicity

Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).[5]

The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats.[6] Numerous studies have been done on the toxicity of gramine to insects harmful to crops in order to assess its potential use as an insecticide.[7]

References

  1. 1 2 Corcuera, L. J. (1993). "Biochemical Basis of the Resistance of the Barley to Aphids". Phytochemistry. 33 (4): 741–747. doi:10.1016/0031-9422(93)85267-U.
  2. ↑ Orechoff, A.; Norkina, S. (1935). "Über die Alkaloide von Arundo Donax L.". Berichte der Deutschen Chemischen Gesellschaft. 68 (3): 436–437. doi:10.1002/cber.19350680312.
  3. 1 2 3 Cheeke, P. R. (1989). Toxicants of Plant Origin, Alkaloids. CRC Press. p. 172. ISBN 0-8493-6990-8.
  4. ↑ Pachter, I. J.; Zacharias, D. E.; Ribeiro, O. (1959). "Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis". Journal of Organic Chemistry. 24 (9): 1285–1287. doi:10.1021/jo01091a032.
  5. ↑ Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z (2013). "Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay". PLOS ONE. 8 (5): e63354. Bibcode:2013PLoSO...863354S. doi:10.1371/journal.pone.0063354. PMC 3653934. PMID 23691032.
  6. ↑ Erspamer, V. (1954). "Pharmacology of Indolealkylamines". Pharmacological Reviews. 6 (4): 425–487. PMID 13236482.
  7. ↑ Corcuera, L. J. (1984). "Effects of Indole Alkaloids from Gramineae on Aphids". Phytochemistry. 23 (3): 539–541. doi:10.1016/S0031-9422(00)80376-3.
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