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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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    PharmaCompass offers a list of Acetonitrile 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 Acetonitrile manufacturer or Acetonitrile supplier for your needs.

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

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    API | Excipient name

    Acetonitrile

    Synonyms

    Cyanomethane, Methyl cyanide, 75-05-8, Ethanenitrile, Ethyl nitrile, Methanecarbonitrile

    Cas Number

    75-05-8

    Unique Ingredient Identifier (UNII)

    Z072SB282N

    About 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.

    Acetonitrile Manufacturers

    A Acetonitrile manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Acetonitrile, including repackagers and relabelers. The FDA regulates Acetonitrile manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Acetonitrile 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 Acetonitrile manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Acetonitrile Suppliers

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

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

    Acetonitrile USDMF

    A Acetonitrile DMF (Drug Master File) is a document detailing the whole manufacturing process of Acetonitrile active pharmaceutical ingredient (API) in detail. Different forms of Acetonitrile DMFs exist exist since differing nations have different regulations, such as Acetonitrile USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Acetonitrile DMF submitted to regulatory agencies in the US is known as a USDMF. Acetonitrile USDMF includes data on Acetonitrile's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Acetonitrile USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Acetonitrile suppliers with USDMF on PharmaCompass.

    Acetonitrile GMP

    Acetonitrile 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 Acetonitrile 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 Acetonitrile GMP manufacturer or Acetonitrile GMP API supplier for your needs.

    Acetonitrile CoA

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

    Acetonitrile CoA mostly includes findings from lab analyses of a specific batch. For each Acetonitrile 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.

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