Gramine

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Gramine
Chemical structure of gramine
Identifiers
CAS number 87-52-5 7pxY
ChemSpider 6625 7pxY
KEGG C08304 7pxY
ChEMBL CHEMBL254348 7pxY
Jmol-3D images Image 1
Properties
Molecular formula C11H14N2
Molar mass 174.24 g/mol
Melting point 138-139 °C
Hazards
NFPA 704

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 14pxY (verify) (what is: 10pxY/10pxN?)
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] 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.

Gramine can be synthesized from indole

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.

Retromichael addition of gramine

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 raises blood pressure and heart rate.

References

  1. 1.0 1.1 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. 3.0 3.1 3.2 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. Erspamer, V. (1954). "Pharmacology of Indolealkylamines". Pharmacological Reviews 6 (4): 425–487. PMID 13236482. 
  6. 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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