2-Methylnaphthalene-1,4-diamine

Vitamin K6.svg skin-invert-image 2-Methylnaphthalene-1,4-diamine 83-68-1 correct CAS correct FDA YL68XZ7ZVU 9837191 8012912 DTXSID30431565 1S/C11H12N2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,12-13H2,1H3 BCKLPBBBFNWJHH-UHFFFAOYSA-N CC1=C(C2=CC=CC=C2C(=C1)N)N 11 12 2 yellowish crystals 110-113 °C dihydrochloride is freely soluble 2-Methylnaphthalene-1,4-diamine is a synthetic menadione analog with vitamin K activity.Veldstra H, Wiardi PW 1943 Water soluble antihemorrhagic substances I: synthesis of 2-methyl-4-aminonaphthol-1 hydrochloride and of 2-methyl-1,4-diaminonaphthalene dihydrochloride, the water soluble synthetic vitamins K5 and K6 Recueil des Travaux Chimiques des Pays-Bas 62 2 75–84 10.1002/recl.19430620203 0165-0513The Merck index Budavari S Chapman & Hall Electronic Pub. Division 2000 9781584881292 12th 1581 etal 2-Methylnaphthalene-1,4-diamine was first synthesized in 1925.Veselý V, Kapp J 1925 Sur les dérivés nitres du méthyl-2-naphtalène Recueil des Travaux Chimiques des Pays-Bas 44 4 360–375 10.1002/recl.19250440409 0165-0513 In 1942 two different research groups noted the vitamin K activity of the compound.Baker BR, Carlson GH 1942 Water-soluble compounds with antihemorrhagic activity Journal of the American Chemical Society 64 11 2657–2664 10.1021/ja01263a038 1942JAChS..64.2657B 0002-7863Robinson FA, Holland DO 1948 Preparation of water-soluble derivatives of 2-methylnaphthalene Journal of the Chemical Society 2 182–186 10.1039/JR9480000182 18906382 0368-1769 It forms a dihydrochloride salt (C11H14Cl2N2) with hydrochloric acid and one of the aforementioned research groups suggested the name vitamin K6 for the salt. 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. 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.etal Fiore LD 2001 Anaphylactoid reactions to vitamin K Journal of Thrombosis and Thrombolysis 11 2 175–183 10.1023/A:1011237019082 1573-742X 11406734 975055 Oral toxicity of dihydrochloride for rats is approximately the same as for 4-amino-2-methyl-1-naphthol hydrochloride. References Category:Naphthylamines Category:Vitamin K Category:Substances discovered in the 1920s