2-Methylnaphthalene-1,4-diamine is a synthetic menadione analog with vitamin K activity.[3][2]
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Preferred IUPAC name
2-Methylnaphthalene-1,4-diamine | |
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Properties | |
C11H12N2 | |
Molar mass | 172.231 g·mol−1 |
Appearance | yellowish crystals[1] |
Melting point | 110-113 °C[3][1] |
dihydrochloride is freely soluble[2] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Methylnaphthalene-1,4-diamine was first synthesized in 1925.[1][3] In 1942 two different research groups noted the vitamin K activity of the compound.[3][4][5] It forms a dihydrochloride salt (C11H14Cl2N2) with hydrochloric acid and one of the aforementioned research groups suggested the name vitamin K6 for the salt.[3]
2-Methylnaphthalene-1,4-diamine and its dihydrochloride can be made from 2-methylnaphthalene or its close analogs. Dihydrochloride blackens without melting at about 300 °C.[3]
4-Amino-3-methyl-1-naphthol or its dihydrochloride have not been used as commercial medicinal forms of vitamin K unlike phylloquinone and menadione for example.[6]
Oral toxicity of dihydrochloride for rats is approximately the same as for 4-amino-2-methyl-1-naphthol hydrochloride.[3]