Gramine

Gramine
Names
	Preferred IUPAC name 1-(1H-Indol-3-yl)-N,N-dimethylmethanamine
	Other names donaxine
Identifiers
CAS Number	87-52-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28948 ;
ChEMBL	ChEMBL254348 ;
ChemSpider	6625 ;
ECHA InfoCard	100.001.591
EC Number	201-749-8;
KEGG	C08304 ;
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 Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N ; InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 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). verify (what is ?) 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

^ ^a ^b 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.
^ 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.
^ ^a ^b ^c Cheeke, P. R. (1989). Toxicants of Plant Origin, Alkaloids. CRC Press. p. 172. ISBN 0-8493-6990-8.
^ 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.
^ 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.
^ Erspamer, V. (1954). "Pharmacology of Indolealkylamines". Pharmacological Reviews. 6 (4): 425–487. PMID 13236482.
^ 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.

[barley-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.

[toxicants-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.

[pmid23691032-5] 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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