Gramine

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
Gramine
Chemical structure of 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 Edit this at Wikidata
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 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 [77 °F], 100 kPa).
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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 is a close analogue of the psychedelic drug dimethyltryptamine (DMT), but its side chain has one less carbon atom in comparison.[5] In contrast to DMT, gramine does not have significant psychedelic-like behavioral effects in animals.[5] The same is true of 5-methoxygramine (5-MeO-gramine), which failed to substitute for DOM in rodent drug discrimination tests.[6]

Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).[7]

The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats.[8] Numerous studies have been done on the toxicity of gramine and tryptamines to insects harmful to crops in order to assess their potential use as an insecticide.[9]

Recent toxicity evaluations show Gramine to be relatively low toxicity in humans, and to have anti-mutagenic and potential neuroprotective action, as a widely found alkaloid present in Oats and Barley.[10] There are numerous recent studies on the potential health benefits of Gramine.

See also

References

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