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
Names
IUPAC name
3-(Dimethylaminomethyl)indole
Other names
donaxine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.591
EC Number
  • 201-749-8
KEGG
UNII
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)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
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 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 in insects harmful to crops for use as a possible insecticide.[7]

gollark: Skynet: simple websocket-based data transfer (ask if you want the server code).Use with `local skynet = require "skynet"````skynet.receive(channel) - receive a message on the given channel - returns channel, message, metadataskynet.send(channel, data, [meta]) - send a message (can be any JSON-serializable type) on the given channelskynet.listen() - convert "websocket_message"s to "skynet_message"sskynet.open(channel) - opens "channel"```
gollark: https://raw.githubusercontent.com/osmarks/skynet/master/client.lua
gollark: You could just autodownload mEXT/skynet.
gollark: (note that for obvious reasons you cannot *send* to a specific socket ID)
gollark: I mean, the metadata is more of "entire response object", so you also get the ID of the websocket sending it, and the message ID.

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. 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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