4-Amino-2-methyl-1-naphthol

Last updated
4-Amino-2-methyl-1-naphthol
Vitamin K5.svg
Names
Preferred IUPAC name
4-Amino-2-methylnaphthalen-1-ol
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 204-983-9
PubChem CID
UNII
  • InChI=1S/C11H11NO/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6,13H,12H2,1H3
    Key: UGQFCTZXVAPVCS-UHFFFAOYSA-N
  • CC1=C(C2=CC=CC=C2C(=C1)N)O
Properties
C11H11NO
Molar mass 173.215 g·mol−1
AppearanceHCl: white crystalline powder [1]
Solubility HCl: soluble in water, poorly soluble in ethanol, insoluble in diethyl ether [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Amino-2-methyl-1-naphthol is a menadione analog. Its hydrochloride (HCl) salt is often called vitamin K5. The HCl salt has been used as a medicine for vitamin K deficiency under tradenames such as Synkamin, [1] [2] which was sold by Parke-Davis, but has since been discontinued. [3]

Contents

Vitamin K function of the compound was first noted in 1940. [4] [5]

Oral lethal dose for the HCl salt in rats is 0.7 g/kg. [5]

Uses

4-Amino-2-methyl-1-naphthol HCl salt is a vitamin K and prevents bleeding caused by vitamin K deficiency when given via intravenous or intramuscular injections at doses of about 1–3 mg. HCl salt is water-soluble and its parenteral administration requires no emulsifiers [6] [7] unlike fat-soluble phylloquinone for example, which is often in formulations with lecithin or glycocholic acid. [8] Parenterally given 1 mg/ml aqueous solutions and orally taken 4 mg tablets of the HCl salt have been available commercially. [1]

Chemistry

4-Amino-2-methyl-1-naphthol HCl salt has a mass of 209.57 g/mol. [1] It darkens at 262 °C and decays without melting at 280–282 °C. [2]

HCl salt breaks down in aqueous solutions via oxidation which is quite fast at neutral pH. First a pink and later a purple precipitant forms. The colored precipitant is (4-oxy-2-methylnaphtylimine)-2-methyl-1,4-naphthoquinone, which is a condensation reaction product of 4-amino-2-methyl-1-naphthol and menadione. Latter is formed via oxidation and deamination of 4-amino-2-methyl-1-naphthol. [9]

4-Amino-2-methyl-1-naphthol can be made from 2-methylnaphthalene or menadione. [2]

Research

4-Amino-2-methyl-1-naphthol HCl salt prevents the growth of different molds and bacteria. Thus it has been studied as potential food preservative. [10] [9]

HCl salt has been studied as a potential treatment for cancer as it prevents glycolysis in cancer cells, which provides them energy for growth. [11]

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References

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