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Gramine

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Gramine
Chemical structure of gramine
Names
Preferred IUPAC name 1-(1H-Indol-3-yl)-N,N-dimethylmethanamine
Other names donaxine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.591 Edit this at Wikidata
EC Number
  • 201-749-8
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N
  • InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3Key: OCDGBSUVYYVKQZ-UHFFFAOYAK
SMILES
  • c1cccc2c1c(c2)CN(C)C
Properties
Chemical formula 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 diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Occurrence

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

Effects and toxicity

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

The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats. 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.

References

  1. ^ 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. ^ 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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