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Chemistry

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Also known as: Cyanomethane, Methyl cyanide, 75-05-8, Ethanenitrile, Ethyl nitrile, Methanecarbonitrile
Molecular Formula
C2H3N
Molecular Weight
41.05  g/mol
InChI Key
WEVYAHXRMPXWCK-UHFFFAOYSA-N
FDA UNII
Z072SB282N

Acetonitrile
Acetonitrile has many uses, including as a solvent, for spinning fibers, and in lithium batteries. It is primarily found in air from automobile exhaust and manufacturing facilities. Acute (short-term) inhalation exposure results in irritation of mucous membranes. Chronic (long-term) exposure results in central nervous system effects, such as headaches, numbness, and tremors. No data are available on its carcinogenic effects in humans; EPA has classified it as a Group D, not classifiable as to human carcinogenicity.
1 2D Structure

Acetonitrile

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
acetonitrile
2.1.2 InChI
InChI=1S/C2H3N/c1-2-3/h1H3
2.1.3 InChI Key
WEVYAHXRMPXWCK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC#N
2.2 Other Identifiers
2.2.1 UNII
Z072SB282N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acetonitrile, 1-(14)c-labeled

2. Acetonitrile, 3h-labeled

2.3.2 Depositor-Supplied Synonyms

1. Cyanomethane

2. Methyl Cyanide

3. 75-05-8

4. Ethanenitrile

5. Ethyl Nitrile

6. Methanecarbonitrile

7. Methane, Cyano-

8. Acetonitril

9. Cyanure De Methyl

10. Methylkyanid

11. Mecn

12. Methylkyanid [czech]

13. Usaf Ek-488

14. Rcra Waste Number U003

15. Nci-c60822

16. Cyanure De Methyl [french]

17. Acetonitril [german, Dutch]

18. Acetonitrile, Anhydrous

19. Ch3cn

20. Ncme

21. Acetonitrile, Dimer

22. 148642-19-7

23. Acetonitrile With 0.1% Ammonium Acetate

24. Ch3-c#n

25. Chebi:38472

26. Z072sb282n

27. Nsc-7593

28. Acetonitrile With 0.1per Cent Ammonium Acetate

29. Mfcd00001878

30. Acetonitrile [un1648] [flammable Liquid]

31. Acetonitril (german, Dutch)

32. Acetonitrile, For Dna Synthesis

33. Acetnitrile

34. Ethanonitrile

35. 66016-35-1

36. Ccn

37. Hsdb 42

38. Ccris 1628

39. Nsc 7593

40. Acetonitrile, For Hplc, Gradient Grade, >=99.9%

41. Einecs 200-835-2

42. Un1648

43. Rcra Waste No. U003

44. Acetonitile

45. Acetonitnle

46. Acetonitriie

47. Acteonitril

48. Acteonitrile

49. Actonitrile

50. Methylcyanide

51. Methylnitrile

52. Ace-tonitrile

53. Aceto-nitrile

54. Acetonitrile-

55. Unii-z072sb282n

56. Ai3-00327

57. Acetonitrile Acs

58. Cc.equiv.n

59. Acetonitrile Lc-ms

60. Acetonitrile,homopolymer

61. Cyanomethylidyne Radical

62. Dsstox_cid_9

63. Acetonitrile Hplc Grade

64. H3ccn

65. Acetonitrile [ii]

66. Acetonitrile [mi]

67. Acetonitrile, Lcms Grade

68. Bmse000826

69. Bmse000896

70. Acetonitrile [hsdb]

71. Ec 200-835-2

72. Acetonitrile, Hplc Reagent

73. Wln: Nc1

74. Acetonitrile, >=99.5%

75. Dsstox_rid_75320

76. Dsstox_gsid_20009

77. Acetonitrile [mart.]

78. Acetonitrile With Formic Acid

79. Acetonitrile [usp-rs]

80. Acetonitrile, Puriss., 95%

81. Chembl45211

82. Acetonitrile, For Chromatography

83. Dtxsid7020009

84. Acetonitrile Uv/hplc Acs Grade

85. Acetonitrile, Analytical Standard

86. Acetonitrile For Preparative Hplc

87. Acetonitrile, Ar, >=99.5%

88. Acetonitrile, Environmental Grade

89. Nsc7593

90. Acetonitrile, Anhydrous, 99.8%

91. Acetonitrile, >=99.5% (gc)

92. Acetonitrile, Hplc Gradient Grade

93. Amidite Diluent, For Dna Synthesis

94. Str02933

95. Acetonitrile, Far Uv/gradient Grade

96. Tox21_202481

97. Acetonitrile, Hplc Grade (far Uv)

98. Acetonitrile, P.a., Dry, 99.9%

99. Acetonitrile, Reagentplus(r), 99%

100. C1151

101. Stl283937

102. Acetonitrile, Spectrophotometric Grade

103. Acetonitrile, >=99.8%, For Hplc

104. Acetonitrile, For Hplc, >=99.9%

105. Akos000269067

106. Acetonitrile, Hplc Plus, >=99.9%

107. Na 1648

108. Un 1648

109. Acetonitrile, >=99.5%, Acs Reagent

110. Acetonitrile, Acs Reagent, >=99.5%

111. Acetonitrile, Aldrasorb(tm), 99.8%

112. Acetonitrile, Purum, >=99.0% (gc)

113. Cas-75-05-8

114. Acetonitrile (for Hplc) Isocratic Grade

115. Acetonitrile, Hplc Grade, >=99.93%

116. Ncgc00091552-01

117. Ncgc00260030-01

118. Acetonitrile 1000 Microg/ml In Methanol

119. Acetonitrile, Purification Grade, 99.8%

120. Ultrapure Acetonitrile, For Dna Synthesis

121. Acetonitrile With 0.1% Formic Acid (v/v)

122. Acetonitrile, Biotech. Grade, >=99.93%

123. Acetonitrile, P.a., Acs Reagent, 99.8%

124. Acetonitrile, Saj First Grade, >=99.0%

125. A0060

126. A0293

127. A0793

128. Acetonitrile, Jis Special Grade, >=99.5%

129. Ft-0621807

130. Ft-0621808

131. Acetonitrile, Anhydrous, Zero2(tm), 99.8%

132. Acetonitrile, For Hplc-gc, >=99.8% (gc)

133. Acetonitrile, For Uhplc, For Mass Spectrometry

134. Acetonitrile, Supergradient Hplc Grade (far Uv)

135. Acetonitrile, Spectrophotometric Grade, >=99.5%

136. Q408047

137. Acetonitrile, For Hplc, For Uv, >=99.9% (gc)

138. Acetonitrile, Puriss. P.a., Acs Reagent, 99.8%

139. J-008497

140. Acetonitrile, For Preparative Hplc, >=99.8% (gc)

141. Acetonitrile, For Synthesis Of Dna, >=99.9% (gc)

142. Acetonitrile, Hplc Plus, >=99.9%, Poly-coated Bottles

143. Acetonitrile Solution, Contains 0.035 % (v/v) Acetic Acid

144. Acetonitrile Solution, Contains 0.05 % (v/v) Acetic Acid

145. Acetonitrile Solution, Contains 0.1 % (v/v) Acetic Acid

146. Acetonitrile, Electronic Grade, 99.999% Trace Metals Basis

147. Acetonitrile, For Hplc, Gradient Grade, >=99.9% (gc)

148. Acetonitrile, For Hplc, Gradient Grade, >=99.90% (gc)

149. Acetonitrile, Puriss. P.a., Acs Reagent, >=99.5% (gc)

150. Acetonitrile Solution, Contains 0.1 % (v/v) Ammonium Hydroxide

151. Acetonitrile With 0.1% Ammonium Acetate, Tested For Uhplc-ms

152. Acetonitrile, For Protein Sequence Analysis, >=99.8% (gc)

153. Acetonitrile, For Residue Analysis, Suitable For 5000 Per Jis

154. Acetonitrile, Vetec(tm) Reagent Grade, Anhydrous, >=99.8%

155. Acetonitrile Solution, ~20% In H2o, For Protein Sequence Analysis

156. Acetonitrile Solution, Contains 0.05 % (v/v) Trifluoroacetic Acid

157. Acetonitrile Solution, Contains 0.1 % (v/v) Formic Acid, For Hplc

158. Acetonitrile, Preparateur, >=99.9% (gc), Customized Plastic Drum

159. Acetonitrile Solution, Contains 0.1 % (v/v) Trifluoroacetic Acid, For Hplc

160. Acetonitrile Solution, For Hplc, Acetonitrile:water 56 : 44% (w/w)

161. Acetonitrile, >=99.8%, For Residue Analysis, Suitable For 1000 Per Jis

162. Acetonitrile, >=99.8%, For Residue Analysis, Suitable For 300 Per Jis

163. Acetonitrile, Puriss. P.a., Acs Reagent, Reag. Ph. Eur., >=99.5% (gc)

164. Acetonitrile Solution, Contains 0.035 % (v/v) Trifluoroacetic Acid, For Hplc

165. Acetonitrile Solution, Contains 0.1 % (v/v) Formic Acid, For Uhplc, For Mass Spectrometry

166. Acetonitrile Solution, Contains 0.10 % (v/v) Trifluoroacetic Acid, 10.0 % (v/v) Water

167. Acetonitrile Solution, Contains 10.0% Acetone, 40.0% 2-propanol, 0.05% Formic Acid

168. Acetonitrile, Configured For Perkinelmer 8900, Configured For Polygen, For Dna Synthesis

169. Acetonitrile, Pharmaceutical Secondary Standard; Certified Reference Material

170. Acetonitrile, Preparateur, >=99.9% (gc), One-time Steel-plastic (sp) Drum

171. Alcohol Determination - Acetonitrile, United States Pharmacopeia (usp) Reference Standard

172. Acetonitrile Solution, Contains 5 % (v/v) Water, 0.05 % (w/v) Ammonium Formate, 0.1 % (v/v) Formic Acid, For Hplc

173. Acetonitrile Solution, For Hplc, Acetonitrile:water 5:95% (v/v), 10 Mm Ammoniumbicarbonate, Ph 10,0

174. Acetonitrile Solution, Nmr Reference Standard, 0.23 Wt. % In D2o (99.9 Atom % D), Water 0.05 Wt. %, Nmr Tube Size 6.5 Mm X 8 In.

175. Residual Solvent - Acetonitrile, Pharmaceutical Secondary Standard; Certified Reference Material

176. Residual Solvent Class 2 - Acetonitrile, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 41.05 g/mol
Molecular Formula C2H3N
XLogP30
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass41.026549100 g/mol
Monoisotopic Mass41.026549100 g/mol
Topological Polar Surface Area23.8 Ų
Heavy Atom Count3
Formal Charge0
Complexity29.3
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

Like hydrogen cyanide (HCN), acetonitrile (ACN) is readily absorbed from the lungs and gastrointestinal tract, and is distributed throughout the body in both humans and laboratory animals. In a group of male and female test subjects, 74% of inhaled ACN was absorbed when cigarette smoke was held in the mouth for 2 seconds (and not inhaled), and 91% was absorbed when smoke was inhaled. Autopsy of an individual who died 2 days following inhalation of ACN vapors showed that cyanide reaches the spleen, lungs, and kidneys, but was not detected in the liver

U.S. Environmental Protection Agency's Integrated Risk Information System (IRIS).Toxicological Review of Acetonitrile (75-05-8). Available from, as of July 28, 2008: https://cfpub.epa.gov/ncea/iris/index.cfm


The kinetics of distribution were studied in mice following intravenous dosing. After 5 minutes, the highest levels of radioactivity were found in the liver and kidney with levels declining with time. At 24 and 48 hours, radioactivity was found highest in the gastrointestine, thymus, liver, and testes. Covalent binding studies showed approximately one-half of the radioactivity in the liver bound to macromolecular fractions. The radioactivity in other organs was primarily in the lipid fractions. Acetonitrile was shown to be converted to cyanide by rat nasal and liver tissues with the maximum rate being ten times higher per gram of protein in the nasal tissue than in any other tissue monitored.

American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's with Other World Wide Occupational Exposure Values. CD-ROM Cincinnati, OH 45240-1634 2007.


Whole body autoradiography in male mice injected intravenously with acetonitrile (ACN) radiolabeled with (14)C in the methyl group indicated that radioactivity was widely distributed throughout the body (e.g., liver, thymus, and reproductive organs). Interestingly, nonvolatile radioactivity was also observed in nasal secretions, mouth cavity, esophagus, and stomach contents. One could infer from these observations that ACN could also distribute to the stomach upon inhalation exposure.

U.S. Environmental Protection Agency's Integrated Risk Information System (IRIS).Toxicological Review of Acetonitrile (75-05-8). Available from, as of July 28, 2008: https://cfpub.epa.gov/ncea/iris/index.cfm


Absorption of acetonitrile (ACN) is rapid in beagle dogs exposed to 16,000 ppm ACN (26,880 mg/cu m) vapors for 4 hours, based on blood cyanide concentrations peaking and reaching steady-state concentrations of 305-433 ug/100 mL after approximately 3 hours.

U.S. Environmental Protection Agency's Integrated Risk Information System (IRIS).Toxicological Review of Acetonitrile (75-05-8). Available from, as of July 28, 2008: https://cfpub.epa.gov/ncea/iris/index.cfm


For more Absorption, Distribution and Excretion (Complete) data for ACETONITRILE (6 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

Inorganic cyanide has long been known to react with trivalent iron of cytochrome oxidase in mitochondria and block the reduction of oxygen needed for cellular respiration, thus leading to cytotoxic anoxia. The toxicity of acetonitrile (ACN) is believed to be mediated, in part, through this mechanism. ACN is metabolized to inorganic cyanide, but the conversion occurs slowly compared to other nitriles (which may explain the delay in onset of acute symptoms). /Previous studies/ suggest that the conversion to cyanide is oxygen- and NADPH-dependent, possibly mediated by P450 isozyme (2E1 or P-450j). Some /studies/ suggest that ACN produces cyanohydrin by a P450 reaction, which is then decomposed by catalase to release cyanide. Formaldehyde and formic acid are also postulated to be by-products of ACN metabolism. Cyanide can be further oxidized to thiocyanate, a less toxic compound that is excreted in urine, but one that may interfere with thyroid function. Conversion is mediated by rhodanese, a sulfurtransferase found in liver and human nasal respiratory mucosa. A minor urinary metabolite that has been detected after administration of ACN in drinking water to rats is 2-aminothiolazine-4-carboxylic acid. Cyanide also can be oxidized to cyanate ion with further oxidation to formic acid).

U.S. Environmental Protection Agency's Integrated Risk Information System (IRIS).Toxicological Review of Acetonitrile (75-05-8). Available from, as of July 28, 2008: https://cfpub.epa.gov/ncea/iris/index.cfm


/Male Wistar/ rats given 2340 or 1500 mg/kg died within 3 to 28 hr after the intraperitoneal injection, but rats given 600 mg/kg survived with no apparent symptoms. After administration of 2340 mg/kg, concentrations of acetonitrile and free and combined cyanide in various organs ranged from 900 to 1700 mg/kg, 200 to 3500 ug/kg, and 3.5 to 17 mg/kg tissue, respectively. Mean total urinary acetonitrile and free and combined cyanide (essentially all thiocyanate) excreted during the 11 days following an intraperitoneal injection of 600 mg/kg were 28, 0.2 and 12 mg, respectively. These values were equivalent to 3, 0.035 and 2.3% of the acetonitrile dose, respectively. Urinary acetonitrile was detectable for 4 days after dosing, whereas free and combined cyanide were detectable until 11 days, at which time the animals were sacrificed.

IPCS/WHO; Environmental Health Criteria 154: Acetonitrile (1993). Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc154.htm


Thiocyanate was measured as index of cyanide ion release in urine of rats given equimolar doses of nitriles. More thiocyanate was excreted after oral administration than after ip administration. Oral administration of acetonitrile yielded 37% of dose as thiocyanate (SCN-), whereas after ip injection, 4.5% of dose was excreted as thiocyanate. /nitriles/

PMID:6128199 SILVER EH ET AL; DRUG METAB DISPOS 10 (5): 495-8 (1982)


When rat liver microsomes were incubated with glycolonitrile or acetonitrile, cyanide was liberated without the formation of formaldehyde. Based on the amount of cytochrome P450 in the microsomal preparation and the rates of cyanide formed, the action of an enzyme system was postulated in the metabolism of both compounds.

PMID:3801055 Freeman JJ, Hayes EP; Biochem Pharmacol 36 (1): 184-7 (1987)


For more Metabolism/Metabolites (Complete) data for ACETONITRILE (7 total), please visit the HSDB record page.


4.3 Biological Half-Life

Whole body: 15-32 hours; [TDR, p. 23]

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. 23


A case of suicidal oral acetonitrile ingestion in a previously healthy 30-year-old man /was reported/. He ingested about 5 mL (64 mg/kg) of acetonitrile (98%) and, 30 min later, about 1 mL of ammonia and vomited once. ...Half-lives were calculated for acetonitrile and cyanide and found to be 32 and 15 hr, respectively.

IPCS/WHO; Environmental Health Criteria 154: Acetonitrile (1993). Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc154.htm


4.4 Mechanism of Action

Aliphatic nitriles (including acetonitrile) possess little if any acute toxicity in absence of normal hepatic function & are activated by hepatic mechanisms to release cyanide which accounts for major acute toxic effects.

PMID:6267734 WILLHITE CC, SMITH RP; TOXICOL APPL PHARMACOL 59 (3): 589-602 (1981)


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01-Jan-2021
31-Aug-2024
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