Gramine

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]

Gramine

Chemical structure of gramine
Names
Preferred IUPAC name 1-(1H-Indol-3-yl)-N,N-dimethylmethanamine
Other names donaxine
Identifiers
CAS Number	87-52-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28948 Y
ChEMBL	ChEMBL254348 Y
ChemSpider	6625 Y
ECHA InfoCard	100.001.591
EC Number	201-749-8
KEGG	C08304 Y
PubChem CID	6890
UNII	FGQ8A78L14
CompTox Dashboard (EPA)	DTXSID3058955
InChI InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 Y Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N Y 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
SMILES c1cccc2c1c(c[nH]2)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)	2 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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

• Dimethyltryptamine (DMT)