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
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
| Molecular Weight | 144.17 g/mol |
|---|---|
| Molecular Formula | C10H8O |
| XLogP3 | 2.8 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Exact Mass | Da |
| Monoisotopic Mass | Da |
| Topological Polar Surface Area | 20.2 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 133 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
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. 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
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
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.
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)
BUILDING BLOCK
