4-Amino-2-methyl-1-naphthol

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4-Amino-2-methyl-1-naphthol
Names
Preferred IUPAC name
4-Amino-2-methylnaphthalen-1-ol
Identifiers
3D model (
JSmol
)
ChemSpider
EC Number
  • 204-983-9
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
Appearance HCl: 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 water-soluble 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]

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

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]

References

  1. ^
    ISBN 9780126337631
    .
  2. ^
    ISBN 9781584881292
    .
  3. S2CID 975055
    .
  4. ISSN 0021-9258
    .
  5. ^
    ISSN 0165-0513
    .
  6. ISSN 0272-5533
    .
  7. ISSN 0022-3476
    .
  8. PMID 9875038
    .
  9. ^
    PMID 5963891
    .
  10. PMID 5867645
    .
  11. PMID 29725454
    .
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