Title: Gramine
CAS Registry Number: 87-52-5
CAS Name: N,N-Dimethyl-1H-indole-3-methanamine
Additional Names: 3-(dimethylaminomethyl)indole
Trademarks: Donaxine
Molecular Formula: C11H14N2
Molecular Weight: 174.24
Percent Composition: C 75.83%, H 8.10%, N 16.08%
Literature References: In chlorophyll-deficient mutants of barley: Euler et al., Z. Physiol. Chem. 217, 23 (1933). In the Asiatic reed Arundo donax L., Gramineae: Orechoff, Norkina, Ber. 68, 436 (1935). From Acer saccharinum L. (the Silver Maple) and A. rubrum L., Aceraceae: Pachter et al., J. Org. Chem. 24, 1285 (1959); Pachter, J. Am. Pharm. Assoc. Sci. Ed. 48, 670 (1959). Synthesis: Kühn, Stein, Ber. 70, 567 (1937). Biosynthesis from tryptophan in barley: Bowden, Marion, Can. J. Chem. 29, 1037 (1951); O'Donovan, Leete, J. Am. Chem. Soc. 85, 461 (1963); Gower, Leete, ibid. 3683; see also Gross et al., Tetrahedron Lett. 1971, 4047.
Properties: Shiny, flat needles or plates from acetone, mp 138-139°. Absorption spectrum: Kanakoa et al., Chem. Pharm. Bull. 8, 294 (1960). Sol in alcohol, ether, chloroform; slightly sol in cold acetone. Practically insol in petr ether, water.
Melting point: mp 138-139°
Derivative Type: Hydrochloride
Molecular Formula: C11H14N2.HCl
Molecular Weight: 210.70
Percent Composition: C 62.70%, H 7.18%, N 13.30%, Cl 16.83%
Properties: Crystals from ethanol + ether, dec 191°. Sol in water.
Derivative Type: Methiodide
Molecular Formula: C11H14N2.CH3I
Molecular Weight: 316.18
Percent Composition: C 45.58%, H 5.42%, N 8.86%, I 40.14%
Properties: Crystals from methanol + benzene, mp 168-169°. Sol in water: Geissman, Armen, J. Am. Chem. Soc. 74, 3916 (1952).
Melting point: mp 168-169°
Granaticin Grandisol Granisetron Granulocyte Colony-Stimulating Factor Granulocyte-Macrophage Colony-Stimulating Factor

Chemical structure of gramine
CAS number 87-52-5 YesY
ChemSpider 6625 YesY
KEGG C08304 YesY
Jmol-3D images Image 1
Molecular formula C11H14N2
Molar mass 174.24 g/mol
Melting point 138-139 °C
NFPA 704
NFPA 704.svg
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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]