Gramine: Difference between revisions
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| MolarMass = 174.24 g/mol |
| MolarMass = 174.24 g/mol |
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| MeltingPtC = 138 to 139 |
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Revision as of 23:07, 1 November 2015
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| Names | |
|---|---|
| IUPAC name
1-(1H-indol-3-yl)-N,N-dimethylmethanamine
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.591 |
| KEGG | |
CompTox Dashboard (EPA)
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| 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) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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] and Phalaris[3] plant species.
Synthesis
Despite being widely available in several plant species, gramine is far easier to synthesize directly from indole via a Mannich reaction with dimethylamine and formaldehyde.
Uses
Gramine is used mostly in synthetic organic chemistry as a starting material for tryptophan syntheses.
All reactions of gramine follow the same general reaction scheme. Gramine is reacted with a strong electrophile, such as methyl iodide, to form the quaternary ammonium salt 2. The ammonium salt will undergo a Hofmann elimination or Michael addition to give the very active intermediate 3, which can accept a wide range of nucleophiles to give the desired product 4.
Toxicity
The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats.[5] Numerous studies have been done on the toxicity in insects harmful to crops for use as a possible insecticide.[6]
Gramine is a norepinephrine reuptake inhibitor in synaptic vesicles.[citation needed] Resulting effects of extra norepinephrine raise blood pressure and heart rate.
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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ 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.