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Chemistry

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Also known as: Naphthalen-2-ol, 135-19-3, Beta-naphthol, 2-naphthalenol, Betanaphthol, 2-hydroxynaphthalene
Molecular Formula
C10H8O
Molecular Weight
144.17  g/mol
InChI Key
JWAZRIHNYRIHIV-UHFFFAOYSA-N
FDA UNII
P2Z71CIK5H

2-Naphthol
1 2D Structure

2-Naphthol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
naphthalen-2-ol
2.1.2 InChI
InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H
2.1.3 InChI Key
JWAZRIHNYRIHIV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C2C=C(C=CC2=C1)O
2.2 Other Identifiers
2.2.1 UNII
P2Z71CIK5H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-hydroxynaphthalene

2. 2-naphthol, (1+)

3. 2-naphthol, 1,4,5,8-(14)c4-labeled

4. 2-naphthol, 7-(14)c-labeled

5. 2-naphthol, 8-(14)c-labeled

6. 2-naphthol, Bismuth Salt

7. 2-naphthol, Magnesium Salt

8. 2-naphthol, Potassium Salt

9. 2-naphthol, Sodium Salt

10. 2-naphthol, Titanium(4+) Salt

11. Beta-naphthol

2.3.2 Depositor-Supplied Synonyms

1. Naphthalen-2-ol

2. 135-19-3

3. Beta-naphthol

4. 2-naphthalenol

5. Betanaphthol

6. 2-hydroxynaphthalene

7. Isonaphthol

8. Developer Bn

9. Naphthol B

10. 2-naphtol

11. Azogen Developer A

12. Beta-naphtol

13. Beta-napthol

14. Developer A

15. Developer Ams

16. Beta-hydroxynaphthalene

17. 2-naftolo

18. 2-naftol

19. Developer Sodium

20. C.i. Developer 5

21. .beta.-naphthol

22. Beta-naphthyl Alcohol

23. Beta-monoxynaphthalene

24. Beta-naftol

25. Beta-naftolo

26. Beta-naphthyl Hydroxide

27. Naphthol, Beta

28. C.i. Azoic Coupling Component 1

29. .beta.-hydroxynaphthalene

30. Antioxygene Bn

31. .beta.-naftolo

32. .beta.-naphtol

33. .beta.-napthol

34. .beta.-naftol

35. Nsc 2044

36. C.i. 37500

37. Mfcd00004067

38. .beta.-naphthyl Alcohol

39. .beta.-monoxynaphthalene

40. .beta.-naphthyl Hydroxide

41. 2-naphthalenol, Homopolymer

42. P2z71cik5h

43. Chembl14126

44. Chebi:10432

45. Naphthalen-2-ol (beta-naphthol)

46. Nsc-2044

47. Dsstox_cid_7061

48. Dsstox_rid_78296

49. Dsstox_gsid_27061

50. 26716-78-9

51. 2-naftol [dutch]

52. Beta-naftol [dutch]

53. 2-naphtol [french]

54. Caswell No. 590

55. 2-naftolo [italian]

56. Beta-naphtol [german]

57. Beta-naftolo [italian]

58. 2-napththol

59. Cas-135-19-3

60. Betanaphthol [nf]

61. Hsdb 6812

62. Einecs 205-182-7

63. Unii-p2z71cik5h

64. Epa Pesticide Chemical Code 010301

65. Hydronaphthol

66. Ai3-00081

67. 2-napthol

68. Napthalen-2-ol

69. 2-naphthylalcohol

70. Naphth-2-ol

71. Naphthol As-ptr

72. Naphthol, .beta.

73. 03v

74. Einecs 215-322-9

75. 2-hydroxy Naphthalene

76. 2-naphthol, Reagent

77. 2-naphthol, Purified

78. Brn 1817321

79. 2-naphthol, 98%

80. 2-naphthol, 99%

81. Naphth-2-ol, 10

82. Beta.-hydroxynaphthalene

83. Microcidin (salt/mix)

84. Betanaphthol [ii]

85. 2-naphthol [mi]

86. 2-naphthol, 98.5%

87. Betanaphthol [hsdb]

88. Ec 205-182-7

89. 2-naphthol [inci]

90. Schembl28781

91. Wln: L66j Cq

92. Betanaphthol [mart.]

93. Betanaphthol [who-dd]

94. 2-naphthol(flakes Or Chunks)

95. Sgcut00131

96. 2-naphthol, Lr, >=98%

97. Dtxsid5027061

98. Nsc2044

99. 4b32

100. Sodium 2-naphthoxide (salt/mix)

101. Hms3264n15

102. Pharmakon1600-01504501

103. Zinc967928

104. Hy-y0110

105. To_000010

106. Tox21_201884

107. Tox21_303038

108. Bdbm50159250

109. Nsc758883

110. S6035

111. Stl281866

112. Akos000119842

113. Am86551

114. Ccg-213932

115. Hr-0304

116. Nsc-758883

117. 2-naphthol 1000 Microg/ml In Methanol

118. 2-naphthol, Purum, >=98.0% (gc)

119. Ncgc00249132-01

120. Ncgc00257077-01

121. Ncgc00259433-01

122. Ac-10464

123. 2-naphthol, Bioxtra, >=99.0% (gc)

124. Sbi-0207084.p001

125. 2-naphthol, Saj First Grade, >=98.0%

126. Tolnaftate Impurity A [ep Impurity]

127. Cs-0008403

128. Ft-0613121

129. N0027

130. 2-naphthol, Fluorescence Indicator, >=99.0%

131. D86186

132. Ab01314260_03

133. 4-06-00-04208 (beilstein Handbook Reference)

134. A806896

135. Ab-131/40299865

136. Q949232

137. Sr-01000872753

138. Q-200736

139. Sr-01000872753-1

140. Brd-k21164796-001-01-0

141. Z57127515

142. F0001-0455

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 144.17 g/mol
Molecular Formula C10H8O
XLogP32.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass144.057514874 g/mol
Monoisotopic Mass144.057514874 g/mol
Topological Polar Surface Area20.2 Ų
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

2-Naphthol ... has had medical uses as a counterirritant in alopecia, also as an anthelmintic, and as an antiseptic in treatment of scabies.

Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 655


4.2 Drug Warning

2-Naphthol-containing pastes should be applied only for short periods of time and to a limited area not exceeding 150 square cm.

Marzulli, F.N., H.I. Maibach. Dermatotoxicology 4th ed. New York, NY: Hemisphere Publishing Corp., 1991., p. 864


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Between 5 and 10% of a cutaneous dose /of 2-naphthol/ has been recovered from the urine ... .

Marzulli, F.N., H.I. Maibach. Dermatotoxicology 4th ed. New York, NY: Hemisphere Publishing Corp., 1991., p. 864


5.2 Metabolism/Metabolites

Several pathways of drug metabolizing enzyme activity were measured in hepatic fractions of cattle, sheep, goats, chickens, turkeys, ducks, rabbits and rats. The pathways examined included the O-demethylation of p-nitrophenol, microsomal ester hydrolysis of procaine and glucuronidation of p-nitrophenol, and the cytosolic acetylation of sulfamethazine and sulfation of 2-naphthol. For most enzymatic pathways measured, goats were more similar to sheep (wether) than to cattle (steers). The exception was UDP-glucuronyltransferase activity, which was significantly higher for the goat than for any other species studied. Within the avian subset, the chicken and turkey were usually the most similar species. The activities of arylsulfotransferase isozymes III and IV were particularly low for the duck compared to the chicken and turkey. N-acetyltransferase activity was very high for rabbits and very low for sheep and goats.

PMID:2905957 Short CR et al; Comp Biochem Physiol C 91 (2): 419-24 (1988)


Several pathways of drug metabolizing enzymic activity were measured in hepatic fractions of the channel catfish and rat using model substrates. The pathways examined included the O-demethylation of p-nitroanisole, microsomal ester hydrolysis of procaine and glucuronidation of p-nitrophenol and the cytosolic acetylation of sulfamethazine and sulfation of 2-naphthol. Catfish liver preparations were incubated at both 25 C and 37 C. The oxidative metabolism of p-nitrophenol was only 1/8 of that of the rat at 37 C and 1/12 that of the rat at 25 C. Procaine ester hydrolysis was negligible in catfish microsomal preparations. At 37 C, p-nitrophenol glucuronidation was equivalent in catfish and rat microsomes. Catfish cytosolic preparations exhibited N-acetyltransferase and arylsulfotransferase nearly comparable to those of the rat. Rates of glucuronidation and sulfation were higher at 37 C than at 25 C in hepatic fractions of the catfish.

PMID:2898990 Short CR et al; Comp Biochem Physiol C 89 (2): 153-7 (1988)


To characterize the substrate specificities of various isozymes of carboxylesterases, a series of carbonates, thiocarbonates, carbamates, and carboxylic acid esters containing alpha- or beta-naphthol or p-nitrophenol as leaving groups were tested as substrates of human, rat and mouse liver microsomal esterases; hydrolases A and B from rat liver microsomes were also tested. The carbonates, thiocarbonates, and carboxylic esters of alpha-naphthol were cleaved more rapidly than the corresponding beta-naphthol isomers by the mammalian liver esterases. The majority of the substrates was consistently hydrolyzed at higher rates by hydrolase B compared with hydrolase A. Compared with the corresponding carboxylates, the carbonate moiety of alpha- and beta-naphthol and p-nitrophenol lowered the specific activities of the enzymes by about 5 fold but improved stability under basic conditions. Human and mouse liver microsomal esterase activities were 5 orders of magnitude lower than the esterase activities of hydrolase B. The functional group and lipophilicity of the substrate structure influenced the activity of mammalian esterases.

PMID:8321828 Huang TL et al; Pharm Res 10: 639-48 (1993)


The inhibition of hydroxysteroid-sulfotransferase (ST) activity in the rat liver by alkylamines was investigated. Liver homogenates were prepared from Wistar rats, and cytosolic fractions were obtained. ST activities towards dehydroepiandrosterone (DHEA), androsterone (AS), and 2-naphthol (2NA) were assayed. Cytosolic fractions were fractionated by column chromatography. Triethylamine, which was used as an elution solvent for column chromatography to purify chemically synthesized 3-phosphoadenosine-5-phosphosulfate (PAPS) inhibited androgen sulfation with AS and DHEA, but did not affect ST activities with cortisol and 2-NA. The sulfate donor ability of various PAPS preparations were compared. Fourteen primary, secondary, and tertiary amines were examined for inhibitory actions on ST activities towards DHEA, cortisol, and 2-NA. A secondary amine, di-n-butylamine, and three tertiary amines, triethylamine, tri-n-propylamine and tri-n-butylamine, inhibited DHEA ST activity by 40 to 60%, irrespective of sex. However, 2-NA and cortisol ST activities were not affected to any significant extent. Lineweaver Burk plots with partially purified hydroxysteroid ST indicated that the inhibition by triethylamine fitted a noncompetitive inhibition. The /results/ conclude that glucocorticoid ST appears to be distinct from the hydroxysteroid ST, and that this has implications for the inhibition of human liver ST activities by synthetic steroids and tertiary amines given as drugs.

Matsui M et al; Biochem Pharmacology 46 (3): 465-70 (1993)


For more Metabolism/Metabolites (Complete) data for 2-NAPHTHOL (8 total), please visit the HSDB record page.


2-Naphthol is a known human metabolite of naphthalene.

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


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