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Also known as: 90-15-3, Naphthalen-1-ol, Alpha-naphthol, 1-naphthalenol, 1-hydroxynaphthalene, Furro er
Molecular Formula
C10H8O
Molecular Weight
144.17  g/mol
InChI Key
KJCVRFUGPWSIIH-UHFFFAOYSA-N
FDA UNII
2A71EAQ389

CAS 90-15-3
1-naphthol (1N) is a metabolite of carbaryl and naphthalene that is an intermediate in Metabolism of xenobiotics by cytochrome P450. It is generated by spontaneous reaction from (1R,2S)-Naphthalene epoxide then is it converted to 1,4-Dihydroxynaphthalene. Although 1-Naphthol is not persistent in the body, a single urine sample may adequately predict exposure over several months to chlorpyrifos, which is a broad-spectrum organophosphate insecticide. In adult men, TCPY and 1N were associated with reduced testosterone levels (A3198, A3199).
1 2D Structure

CAS 90-15-3

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
naphthalen-1-ol
2.1.2 InChI
InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
2.1.3 InChI Key
KJCVRFUGPWSIIH-UHFFFAOYSA-N
2.2 Other Identifiers
2.2.1 UNII
2A71EAQ389
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-hydroxynaphthalene

2. 1-naphthol, 1-(14)c-labeled

3. 1-naphthol, 2-(13)c-labeled

4. 1-naphthol, Ion(1+)

5. 1-naphthol, Lithium Salt

6. 1-naphthol, Potassium Salt

7. 1-naphthol, Sodium Salt

8. Alpha-naphthol

2.3.2 Depositor-Supplied Synonyms

1. 90-15-3

2. Naphthalen-1-ol

3. Alpha-naphthol

4. 1-naphthalenol

5. 1-hydroxynaphthalene

6. Furro Er

7. Fouramine Ern

8. Fourrine Ern

9. Tertral Ern

10. Basf Ursol Ern

11. Ursol Ern

12. Fourrine 99

13. Nako Trb

14. Zoba Ern

15. Durafur Developer D

16. Alpha-hydroxynaphthalene

17. .alpha.-naphthol

18. C.i. Oxidation Base 33

19. 1-naphthyl Alcohol

20. Nsc 9586

21. Ci Oxidation Base 33

22. Naphthol-1

23. Ccris 1172

24. Naphthyl-1-ol

25. C.i. 76605

26. .alpha.-hydroxynaphthalene

27. Hsdb 2650

28. Naphthol, 1-

29. Einecs 201-969-4

30. Alpha-naphthyl Alcohol

31. Chebi:10319

32. Ci 76605

33. Ai3-00106

34. Unii-2a71eaq389

35. Dtxsid6021793

36. 2a71eaq389

37. Nsc-9586

38. 1-naphtol-

39. 1-naphthol [mi]

40. 1-naphthol [hsdb]

41. Duloxetine Impurity D

42. Dtxcid401793

43. Duloxetine Impurity D [usp Impurity]

44. Duloxetine Hydrochloride Impurity D [ep Impurity]

45. Duloxetine Impurity D (usp Impurity)

46. Duloxetine Hydrochloride Impurity D (ep Impurity)

47. Alphanaphthol

48. 1naphthalenol

49. 1hydroxynaphthalene

50. Alphahydroxynaphthalene

51. 1-naphthol [inci]

52. 201-969-4

53. Inchi=1/c10h8o/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11

54. Kjcvrfugpwsiih-uhfffaoysa-n

55. Un2811

56. Naphthol

57. Naphthalenol

58. 1321-67-1

59. A-naphthol

60. 1-napthol

61. Mfcd00003930

62. Wln: L66j Bq

63. Chembl122617

64. Sgcut00118

65. Nsc9586

66. To_000072

67. C11714

68. Ab-131/40232333

69. Hydroxynaphthalene

70. Cas-90-15-3

71. Napthalenol

72. Alpha-napthol

73. Napthyl Alcohol

74. 1-naphtyol

75. Naphthalene-1-ol

76. Naphthol 1

77. 1-naphtol

78. 8 -naphthol

79. Hydroxy Naphthalene

80. (+)-naphthol

81. 1np

82. Nchembio791-comp4

83. 1-naphthol, Reagent

84. 1-naphthol, Purified

85. Naphth-1-ol, 9

86. Ls-95401

87. 1-naphthol (standard)

88. Schembl3416

89. Alpha-naphthol, 1-naphthol

90. 33420_riedel

91. 35825_riedel

92. N1000_sial

93. N2780_sial

94. 1-naphthol, Pure Pa, 99%

95. 1-naphthol, Lr, >=99%

96. 70438_fluka

97. 70442_fluka

98. Bdbm23450

99. Hy-y1309r

100. 1-naphthol, Bioxtra, >=99%

101. 4b33

102. 1-naphthol, P.a., 99.0%

103. Hy-y1309

104. Tox21_202120

105. Tox21_302768

106. 1-naphthol, >=98.0% (gc)

107. Bbl011611

108. Msk000684

109. Stl163337

110. Zinc00967929

111. Akos000118822

112. Cs-w020125

113. Fn07835

114. Gs-6917

115. 1-naphthol, Reagentplus(r), >=99%

116. Duloxetine Ep Impurity D (1-naphthol)

117. Ncgc00249169-01

118. Ncgc00256563-01

119. Ncgc00259669-01

120. Db-259778

121. St5214429

122. 1-naphthol, Saj Special Grade, >=99.0%

123. 1-naphthol, Vetec(tm) Reagent Grade, 98%

124. N0026

125. N0864

126. Ns00005331

127. En300-19501

128. 1-naphthol, Pestanal(r), Analytical Standard

129. Q408876

130. 1-naphthol, Certified Reference Material, Tracecert(r)

131. 1-naphthol, Puriss., For Fluorescence, >=99.0% (gc)

132. F1908-0108

133. Z104474036

134. 1-naphthol, Puriss. P.a., Reag. Ph. Eur., >=99% (gc)

135. 50356-21-3

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 144.17 g/mol
Molecular Formula C10H8O
XLogP32.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area20.2
Heavy Atom Count11
Formal Charge0
Complexity133
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

1-Naphthol was selectively toxic to human colorectal tumors compared to corresponding normal colonic tissue removed at surgery and maintained in short-term organ culture. Nineteen of 24 tumors studied have shown a significant differential response. Three human colonic adenocarcinoma xenografts, in the short-term organ culture system, displayed the same response to 1-naphthol as primary tumors removed at surgery. 1-Naphthol, 1,2- and 1,4-naphthoquinone were also toxic to two human colonic adenocarcinoma cell lines, LoVo and COLO 206. The selective toxicity of 1-naphthol is mediated in part through an accumulation of 1-naphthol in the tumor tissue due to impaired conjugation by the tumor. The higher concentrations of 1-naphthol may then exert their toxicity either directly or by formation of naphthoquinones. Some indirect evidence was obtained for the possible involvement of 1,2- or 1,4-naphthoquinone in the cytotoxicity of 1-naphthol. Our studies suggest that further studies are warranted of the possible use of 1-naphthol or related compounds as antitumor agents.

PMID:4005142 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1977081 Wilson GD et al; Br J Cancer 51 (6): 853-63 (1985)


4.2 Minimum/Potential Fatal Human Dose

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN), 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB). /BETA-NAPHTHOL/

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-126


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Urinary excretion of (14)C following topical application of ((14)C)naphth-1-ol indicated that about 50% was absorbed percutaneously in man.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 160


Sixty-two workers of a carbochemical plant exposed to benzene, naphthalene, toluene, o-xylene, p-xylene, phenol and pyridine were examined. In urine samples collected before and after occupational exposure significant differences in concn values of phenol (21.7-97.6 mg/l), 1-naphthol (0.1-9.38 mg/l), hippuric acid (95.5-873.9 mg/l) and m-methylhippuric acid (29.0-93.5 mg/l) were found. There was a correlation between benzene and naphthalene in the breathing zone air and phenol and 1-naphthol in the urine of coke plant workers.

PMID:8107574 Bieniek G et al; Medycyna Pracy 44 (6): 579-86 (1993)


Chemical exposure of assemblers handling creosote impregnated wood and of a single worker chiselling coal tar pitch layer was assessed by measuring airborne naphthalene and various polycyclic aromatic hydrocarbons, and by measurement of urinary excretion of 1-naphthol and 1-pyrenol. The sum concn polycyclic aromatic hydrocarbon and of 4-6 aromatic ring containing polycyclic aromatic hydrocarbons were high, 440 ug/cu m and 290 ug/cu m, respectively, when chiselling. In the assemblers workplace, the polycyclic aromatic hydrocarbons concn were about 1/50 of this value. Regarding airborne naphthalene concn the situation was reversed (assemblers, 1000 ug/cu m; chiseller, 160 ug/cu m). Correspondingly, the assemblers urinary 1-naphthol concn were 15-20 times higher than those of the chiseller. The urinary 1-pyrenol concn of the chiseller was 2-4 times higher than among the assemblers. As the estimated pyrene inhalation doses among the assemblers could account only for 2%-25% of the 24 hr pyrenol excretion in the urine, the skin was presumably the main route of uptake. ...

PMID:7591181 Heikkila P et al; Int Arch Occup Environ Health 67 (3): 211-7 (1995)


Oral administration of 45 mg alpha-Naphthol/kg bw resulted in 95% of the administered dose being eliminated within 72 hr after treatment in male mice.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 613


5.2 Metabolism/Metabolites

Yields 1-napthhyl-alpha-D-glucoside ... in blowfly and in grass grub; yields 1-naphthyl phosphate in fly and in grass grub. /from table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. N-3


Yields 1-naphthyl-beta-D-glucuronide in rat, in rabbit, in fly and in mouse. /from table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. N-3


Yields 1-naphthyl sulfate in rat, rabbit, mouse, guinea pig, fly, and grass grub. /from table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. N-3


After 0.1 mmol 1-naphthol injected into intestinal loops (rat in vivo), 70-90% in intestinal venous blood was present as 1-naphthol glucuronide. For 1.0 and 2.0 mmol injections, proportion of 1-naphthol present as 1-naphthol glucuronide was 25-50%.

PMID:590723 TURNER ET AL; GEN PHARMACOL 8 (1): 51-3 (1977)


For more Metabolism/Metabolites (Complete) data for 1-NAPHTHOL (8 total), please visit the HSDB record page.


1-Naphthol has known human metabolites that include 1-Naphthyl glucuronide.

1-Naphthol is a known human metabolite of naphthalene.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.


5.3 Mechanism of Action

The mechanism(s) of toxicity of 1-naphthol and two of its possible metabolites, 1,2- and 1,4-naphthoquinone, to freshly isolated rat hepatocytes has been studied. 1-Naphthol and both naphthoquinones exhibited a dose-dependent toxicity to hepatocytes. [1-14C]-1-Naphthol was metabolised by hepatocytes predominantly to its glucuronic acid and sulphate ester conjugates, but small amounts of covalently bound products were also formed. Blebbing on the surface of the hepatocytes was observed following exposure to 1-naphthol and the naphthoquinones, together with a dose-dependent decrease in intracellular glutathione (GSH), which preceded the onset of cytotoxicity. The toxicity of 1-naphthol and the naphthoquinones was potentiated by dicoumarol, an inhibitor of DT-diaphorase (NAD(P)H:quinone oxidoreductase). This enhanced toxicity was accompanied by a greater amount of surface blebbing, an increased depletion of intracellular GSH, particularly in the case of 1-naphthol and 1,4-naphthoquinone, and a decreased metabolism of 1-naphthol to its conjugates with variable effects on the amount of covalently bound products formed. These results support the suggestion that the toxicity of 1-naphthol may be mediated by the formation of 1,2-naphthoquinone and/or 1,4-naphthoquinone, which may then be metabolised by one electron reduction to naphthosemiquinone radicals. These, in turn, may covalently bind to important cellular macromolecules or enter a redox cycle with molecular oxygen thereby generating active oxygen species. Both of these processes appear to play a role in producing the cytotoxic effects of 1-naphthol.

PMID:6200119 Doherty MD et al; Biochem Pharmcol 33 (4): 543-9 (1984)


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