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Chemistry

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Also known as: Methylbenzene, Toluol, 108-88-3, Phenylmethane, Benzene, methyl-, Methacide
Molecular Formula
C7H8
Molecular Weight
92.14  g/mol
InChI Key
YXFVVABEGXRONW-UHFFFAOYSA-N
FDA UNII
3FPU23BG52

Toluene
A widely used industrial solvent.
1 2D Structure

Toluene

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
toluene
2.1.2 InChI
InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
2.1.3 InChI Key
YXFVVABEGXRONW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC=CC=C1
2.2 Other Identifiers
2.2.1 UNII
3FPU23BG52
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Methylbenzene

2. Toluol

3. 108-88-3

4. Phenylmethane

5. Benzene, Methyl-

6. Methacide

7. Methylbenzol

8. Antisal 1a

9. Toluen

10. Tolu-sol

11. Monomethyl Benzene

12. Methane, Phenyl-

13. Tolueen

14. Toluolo

15. Phenyl Methane

16. 1-methylbenzene

17. Methyl-benzene

18. P-toluene

19. Rcra Waste Number U220

20. Nci-c07272

21. 4-methylbenzene

22. Benzene, Methyl

23. Cp 25

24. Nsc 406333

25. Un 1294

26. Phme

27. Nsc-406333

28. Chembl9113

29. 3fpu23bg52

30. Chebi:17578

31. Toluene, Anhydrous

32. Mfcd00008512

33. Ncgc00090939-02

34. Dsstox_cid_1360

35. Tolueen [dutch]

36. Toluen [czech]

37. Toluene, Analytical Standard

38. Dsstox_rid_76107

39. Dsstox_gsid_21360

40. Tolueno [spanish]

41. Toluolo [italian]

42. Caswell No. 859

43. Tolueno

44. Methyl Benzene

45. Para-toluene

46. Toluene, Acs Reagent, >=99.5%

47. Toluene 1000 Microg/ml In Methanol

48. Cas-108-88-3

49. Ccris 2366

50. Hsdb 131

51. Einecs 203-625-9

52. Un1294

53. Rcra Waste No. U220

54. Epa Pesticide Chemical Code 080601

55. Unii-3fpu23bg52

56. Dracyl

57. Phenyl-methane

58. Toluene Solvent

59. 2-methylbenzene

60. Toluene Solution

61. Toluene-

62. Ai3-02261

63. Meph

64. Titration Solvent

65. 2-methyl Benzene

66. 4-methyl-benzene

67. Benzylidyne Radical

68. Toluene Acs Grade

69. Toluene Hplc Grade

70. Methylbenzene, 9ci

71. Toluene (technical)

72. Toluene, For Hplc

73. Phch3

74. Toluene, Acs Reagent

75. Toluene, Hplc Grade

76. 4i7k

77. Toluene [hsdb]

78. Toluene [iarc]

79. Toluene [inci]

80. Toluene, 99.5%

81. Toluene [mi]

82. Toluene [mart.]

83. Otoline (9ci)

84. Toluene [usp-rs]

85. Toluene Reagent Grade Acs

86. Ec 203-625-9

87. Toluene, Environmental Grade

88. Toluene, Semiconductor Grade

89. Toluene, Lr, >=99%

90. C6h5ch3

91. Toluene [green Book]

92. Wln: 1r

93. Bidd:er0288

94. Toluene, Anhydrous, 99.8%

95. Toluene, Astm, 99.5%

96. Toluene, P.a., 99.5%

97. Gtpl5481

98. Dtxsid7021360

99. Toluene, Ar, >=99.5%

100. Toluene, For Hplc, 99.9%

101. Toluene, Lr, Rectified, 99%

102. Dtxsid00184990

103. Toluene Gc, For Residue Analysis

104. Toluene, Hplc Grade, 99.8%

105. Toluene, Spectrophotometric Grade

106. Toluene 10 Microg/ml In Methanol

107. Toluene, Lr, Sulfur Free, 99%

108. Zinc967534

109. Toluene, Ar, Rectified, 99.5%

110. Toluene, Technical Grade, 95.0%

111. Bcp16202

112. Toluene, For Hplc, >=99.8%

113. Toluene, For Hplc, >=99.9%

114. Toluene, Histology Grade, Practical

115. Toluene, Pra Grade, >=99.8%

116. Toluene 100 Microg/ml In Methanol

117. Tox21_111042

118. Tox21_201224

119. Bdbm50008558

120. Nsc406333

121. Toluene, Purification Grade, 99.8%

122. Akos015840411

123. Zinc100116646

124. Db11558

125. Toluene, Puriss., >=99.5% (gc)

126. Toluene, Saj First Grade, >=99.0%

127. Ncgc00090939-01

128. Ncgc00090939-03

129. Ncgc00258776-01

130. Toluene [un1294] [flammable Liquid]

131. Toluene, Jis Special Grade, >=99.5%

132. Toluene, Laboratory Reagent, >=99.3%

133. 50643-04-4

134. Ramipril Impurity G [ep Impurity]

135. Toluene, For Hplc, >=99.7% (gc)

136. Toluene, Uv Hplc Spectroscopic, 99.5%

137. Toluene, Anhydrous, Zero2(tm), 99.8%

138. Ft-0688208

139. T0260

140. Toluene, Suitable For Determination Of Dioxins

141. C01455

142. Q15779

143. Toluene, Suitable For Scintillation, >=99.7%

144. Toluene Liquid Density, Nist(r) Srm(r) 211d

145. Toluene, For Residue Analysis, >=99.8% (gc)

146. A801937

147. Sr-01000944565

148. Toluene, Acs Spectrophotometric Grade, >=99.5%

149. Sr-01000944565-1

150. Toluene, P.a., Acs Reagent, Reag. Iso, 99.5%

151. Toluene, Suitable For 5000 Per Jis, For Residue Analysis

152. Toluene, Hplc Plus, For Hplc, Gc, And Residue Analysis, >=99.9%

153. Toluene, P.a., Acs Reagent, Reag. Iso, Reag. Ph. Eur., 99.5%

154. Toluene, Suitable For 300 Per Jis, For Residue Analysis, >=99.8%

155. Toluene, Absolute, Over Molecular Sieve (h2o <=0.005%), >=99.7% (gc)

156. Toluene, Pharmaceutical Secondary Standard; Certified Reference Material

157. Toluene, Suitable For 1000 Per Jis, For Residue Analysis, >=99.8%

158. Residual Solvent - Toluene, Pharmaceutical Secondary Standard; Certified Reference Material

159. Toluene, Puriss. P.a., Acs Reagent, Reag. Iso, Reag. Ph. Eur., >=99.7% (gc)

160. 25013-04-1

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 92.14 g/mol
Molecular Formula C7H8
XLogP32.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass92.062600255 g/mol
Monoisotopic Mass92.062600255 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count7
Formal Charge0
Complexity42
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 Minimum/Potential Fatal Human Dose

Lethal levels 1.0 mg%; 10.0 ug/ml

Winek, C.L. Drug and Chemical Blood-Level Data 1985. Pittsburgh, PA: Allied Fischer Scientific, 1985.


Ingestion of approximately 60 mL (625 mg/kg) of toluene proved fatal for a white male mental patient.

Ameno K et al; Forensic Sci Int 41: 255-60 (1989)


4.2 Drug Indication

Used for the removal of ascarids (Toxocara canis and Toxascaris leonina) and hookworms (Ancylostoma caninum and Uncinaria stenocephala) and as an aid in removing tapeworms (Taenia pisiformis, Dipylidium caninum, and Echinococcus granulosus) from dogs and cats.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Solvents

Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant and Hackh's Chemical Dictionary, 5th ed) (See all compounds classified as Solvents.)


5.2 Absorption, Distribution and Excretion

In a group of 37 rotogravure printers a close correlation (rs = 0.78) was found between the time weighted toluene exposure during a five day working week (range 8-416 mg/cu m, median 75) and the concentration of toluene in subcutaneous adipose tissue (range 1.1-20.7 mg/kg, median 3.8). After exposure ceased, the elimination of toluene was followed up in 11 subjects. The toluene concentration in venous blood decreased non-linearly and the elimination curves contained at least three exponential components. The first two had median estimated half times of nine minutes and two hours respectively. The third component, with a median half time of 90 hours, reflected the decline in adipose tissue, which had a median half time of 79 hours (range 44-178). The study showed protracted endogenous toluene exposure from adipose tissue depots long after the end of exogenous exposure. The observations also suggest that the blood toluene concentrations on Monday mornings might be used as an index of the exposure in the previous week.

PMID:2818975 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1009794 Nise G et al; Br J Ind Med 46 (6): 407-11 (1989)


Studies quantifying oral absorption of toluene are limited but have demonstrated nearly 100% absorption following a single oral exposure. In volunteers exposed to an infusion of 2 mg toluene/minute for 3 hours (~5 mg/kg) via a gastric tube, absorption of toluene, measured by monitoring exhaled air for toluene and urine for toluene metabolites, was found to be complete. /Another study/ reported that greater than 99% of a single gavage dose of radiolabeled toluene in rats was eliminated in the urine or expired air, indicating near-total absorption of the exposure dose.

USEPA; Toxicology Review of Toluene (CAS No. 108-88-3) p. 4 (September 2005). Available from, as of February, 2016: https://www.epa.gov/iris/


Toluene is absorbed through human skin slowly, with absorption rates ranging from 14 to 23 mg/sq cm-hour.

USEPA; Toxicology Review of Toluene (CAS No. 108-88-3) p. 4 (September 2005). Available from, as of February, 2016: https://www.epa.gov/iris/


Studies in both humans and animals have shown that the majority of toluene in the body is eliminated in the urine, mainly as metabolites.

USEPA; Toxicology Review of Toluene (CAS No. 108-88-3) p. 4 (September 2005). Available from, as of February, 2016: https://www.epa.gov/iris/


For more Absorption, Distribution and Excretion (Complete) data for TOLUENE (28 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

Toluene is well metabolized, but a portion is exhaled unchanged. Hepatic P450s catalyze metabolism of toluene primarily to benzyl alcohol and lesser amounts of cresols. Benzyl alcohol is converted by ADH and aldehyde dehydrogenase (ALDH) to benzoic acid, which is primarily conjugated with glycine and eliminated in the urine as hippuric acid.

Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 7th ed. New York, NY: McGraw-Hill, 2008., p. 1010


Toluene is metabolized to benzoic acid, followed by hepatic cytochrome P-450 catalyzed glycine conjugation to form hippuric acid. Approximately 75% to 80% of the absorbed toluene is metabolized to benzoic acid, and 62% to 72% is eliminated by humans in the urine as hippuric acid. As the amount of absorbed toluene is increased, the relative importance of the glucuronide conjugated increased. Relatively small amounts appear in urine as the o-cresol (0.12%-0.43%) and p-cresol where they occur as glucuronide and sulfate derivatives. Less than 2% of the absorbed toluene is eliminated in feces.

American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 3


In rats, approx 0.5%-1.1% of the dose is converted to o-cresol and p-cresol and is excreted as glucuronide and sulfate conjugates.

Bakke OM, Scheline RR; Tox Appl Pharm 16: 691-700 (1970) as cited in NRC; Alkyl Benzenes p.221 (1981)


In mammalian species, acidic metabolites are conjugated with glycine to form hippuric acid and phenylacetic acid. In humans, the phenylacetic acid metabolite is also conjugated with glutamine to form phenacetylglutamine.

James MO et al; Proc R Soc Lond Ser B 182: 25-35 (1972) as cited in NRC; Alkyl Benzenes p.219 (1981)


Toluene has known human metabolites that include 4-Methylphenol, Benzyl alcohol, and o-Cresol.

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


5.4 Biological Half-Life

Blood: 0.5 hours (can range up to 90 hours depending upon fat deposition); for hippuric acid in urine: 1.5 hours; [TDR, p. 1145]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 1145


In mice, toluene is eliminated from alveolar air with a biologic half-life of 2.6 hours; elimination from blood and brain occurs with a half-life of 1 hour. In rats, the mean half-time for toluene uptake from air at 1000 to 3000 ppm was 34 minutes and the half-times for the rapid and slow elimination phases were 6 and 90 minutes, respectively. Alveolar and circulating toluene concentrations decrease as a direct function of respiratory and cardiac rates after exposure ceases. The elimination half-time for toluene from human tissue is 0.5 to 2.7 days after inhaling 70 ppm for 2 hours.

American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 3-4


After exposure ceased, the elimination of toluene was followed up in 11 /rotogravure printers/. The toluene concentration in venous blood decreased non-linearly and the elimination curves contained at least three exponential components. The first two had median estimated half times of nine minutes and two hours respectively. The third component, with a median half time of 90 hours, reflected the decline in adipose tissue, which had a median half time of 79 hours (range 44-178).

PMID:2818975 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1009794 Nise G et al; Br J Ind Med 46 (6): 407-11 (1989)


0.083 days (Inhaled as environmental air)

Cleland, J.G., G.L. Kingsbury. Multimedia Environmental Goals for Environmental Assessment. Volume 1. EPA-600/7-77-136a. Research Triangle Park, NC: EPA, Nov. 1977., p. E-146


5.5 Mechanism of Action

The present study demonstrates reductions of dopamine (DA) turnover in various areas of the anterior nucleus caudate of rat by toluene at concentrations lower than the current OSHA threshold limit value (100 ppm). Thus, toluene at low concentrations may produce disturbances in dopaminergic mechanisms of the basal ganglia probably leading to functional changes in sensory-motor integration. The increases in DA turnover in the cholecystokinin (CCK)-DA terminals of the subcortical limbic system induced by high concentrations of toluene may be part of the neurochemical basis for its abuse as a euphoric agent in man.

PMID:7112606 Fuxe K et al; Toxicol Lett 12 (2-3): 115-23 (1982)


Exposure to toluene causes both reversible and irreversible changes in the central nervous system. The effects of toluene inhalation on some specific enzymes and glutamate and GABA receptor binding in defined parts of the rat brain were studied following several exposure schemes. The activities of the transmitter synthesizing enzymes glutamic acid decarboxylase (GAD), choline acetyltransferase (ChAT) and aromatic amino-acid decarboxylase (AAD) were used as markers for permanent loss of neuronal activity. Catecholaminergic neurons showed a 50% reduction in the brain stem after 4 weeks exposure to 250 and 1000 ppm toluene. Following 500 ppm of toluene, 16 hr/day for 3 months, a general increase in the activities was seen. This is most probably due to a reduction in total protein content, to which the activities were related. The neurotransmitters glutamate and GABA had their specific receptor binding increased in most of the brain areas studied, but decreased in some areas. The glial enzyme, glutamine synthetase, has its activity increased in the cerebellar hemisphere following 4 weeks exposure to 1000 ppm. This suggests that glial cells in the area may have proliferated, a frequent phenomenon following CNS damage.

Bjornaes S, Naalsund Lu; Toxicol 49 (2-3): 367-74 (1988)


The effect on energetic metabolism of rat liver mitochondria (RLM) of styrene and other aliphatic benzene derivatives, i.e. toluene, ethylbenzene, alpha-methylstyrene and butylbenzene, is studied. It is shown that these compounds uncouple oxidative phosphorylation and this effect is connected with the stimulation of passive entry of protons into mitochondria. The relationship between hydrophobicity of these compounds and their biological activity and mechanism of uncoupling effect are discussed.

PMID:2904817 Mickiewicz W, Rzeczycki W; Biochem Pharmacol 37 (23): 4439-44 (1988)


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01-Jan-2021
31-Mar-2025
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ABOUT THIS PAGE

Looking for 108-88-3 / Toluene API manufacturers, exporters & distributors?

Toluene manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Toluene API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Toluene manufacturer or Toluene supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Toluene manufacturer or Toluene supplier.

PharmaCompass also assists you with knowing the Toluene API Price utilized in the formulation of products. Toluene API Price is not always fixed or binding as the Toluene Price is obtained through a variety of data sources. The Toluene Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Toluene

Synonyms

Methylbenzene, Toluol, 108-88-3, Phenylmethane, Benzene, methyl-, Methacide

Cas Number

108-88-3

Unique Ingredient Identifier (UNII)

3FPU23BG52

About Toluene

A widely used industrial solvent.

Toluene Manufacturers

A Toluene manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Toluene, including repackagers and relabelers. The FDA regulates Toluene manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Toluene API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Toluene manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Toluene Suppliers

A Toluene supplier is an individual or a company that provides Toluene active pharmaceutical ingredient (API) or Toluene finished formulations upon request. The Toluene suppliers may include Toluene API manufacturers, exporters, distributors and traders.

click here to find a list of Toluene suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Toluene GMP

Toluene Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Toluene GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Toluene GMP manufacturer or Toluene GMP API supplier for your needs.

Toluene CoA

A Toluene CoA (Certificate of Analysis) is a formal document that attests to Toluene's compliance with Toluene specifications and serves as a tool for batch-level quality control.

Toluene CoA mostly includes findings from lab analyses of a specific batch. For each Toluene CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Toluene may be tested according to a variety of international standards, such as European Pharmacopoeia (Toluene EP), Toluene JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Toluene USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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