| Revision as of 23:10, 25 September 2010 editL.tak (talk | contribs)Extended confirmed users, Pending changes reviewers22,225 editsm moved Tris(2-chloroethyl)amine to HN3 (nitrogen mustard): most used common name← Previous edit |
Latest revision as of 13:36, 1 February 2024 edit undo2405:4803:fefb:8f50:80c5:1a95:772b:4af (talk)No edit summaryTag: Visual edit |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Name = Tris(2-chloroethyl)amine |
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| Watchedfields = changed |
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| ImageFile = Nitrogen-mustard-HN3.png |
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| verifiedrevid = 442314920 |
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| ImageFile = Trichlormethine.svg |
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| ImageName = Tris(2-chloroethyl)amine |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = HN3-3D-vdW.png |
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| ImageSize = 160 |
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| ImageName1 = Tris(2-chloroethyl)amine |
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| ImageName = Skeletal formula of 2-Chloro-N,N-bis(2-chloroethyl)ethanamine |
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| ImageFile1 = HN3-3D-vdW.png |
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| IUPACName = 2-chloro-N,N-bis(2-chloroethyl)ethanamine |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| OtherNames = HN3, Compound 9560<br />Nitrogen mustard gas; tris-(2-chloroethyl)amine<br />trichlormethine; trimustine hydrochloride |
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| ImageSize1 = 160 |
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| Section1 = {{Chembox Identifiers |
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| ImageName1 = Spacefill model of 2-Chloro-N,N-bis(2-chloroethyl)ethanamine |
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| CASNo = 555-77-1 |
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| PIN = 2-Chloro-''N'',''N''-bis(2-chloroethyl)ethanamine |
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| SMILES = ClCCN(CCCl)CCCl |
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| OtherNames = Trichlormethine<br>Tris(2-chloroethyl)amine<br />EA-1053<br />TL-145 |
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| Section2 = {{Chembox Properties |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 555-77-1 |
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| Formula = C<sub>6</sub>H<sub>12</sub>Cl<sub>3</sub>N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| MolarMass = 204.53 g mol<sup>−1</sup> |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| Density = 1.24 g/cm<sup>3</sup> |
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| UNII = 66WBM7N0NM |
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| MeltingPt = -3.7 to -4°C |
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| BoilingPt = 143 °C |
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| PubChem = 5561 |
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| ChemSpiderID = 5360 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| MeSHName = 2,2',2+-trichlorotriethylamine |
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| ChEMBL = 443613 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| SMILES = ClCCN(CCCl)CCCl |
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| StdInChI = 1S/C6H12Cl3N/c7-1-4-10(5-2-8)6-3-9/h1-6H2 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = FDAYLTPAFBGXAB-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| Section2 = {{Chembox Properties |
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| C=6 | H=12 | N=1 | Cl=3 |
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| Appearance = Colourless liquid |
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| Odor = Fishy, ammoniacal |
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| Density = 1.24 g mL<sup>−1</sup> |
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| MeltingPtC = −4 to −3.7 |
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| BoilingPtC = 143 |
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| LogP = 1.306 |
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| Section3 = {{Chembox Related |
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| OtherFunction_label = amines |
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| OtherFunction = {{unbulleted list|]|]|]|]|]|]|]|]|]|]|]|]|]}} |
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| OtherCompounds = {{unbulleted list|]|]|]|]}} |
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'''Tris(2-chloroethyl)amine''' is the ] with the ] N(CH<sub>2</sub>CH<sub>2</sub>Cl)<sub>3</sub>. Often abbreviated HN3, it is a powerful ] and a ] (although it is not a gas) used for ]. HN3 was the last of the nitrogen mustard agents developed. It was designed as a military agent and is the only one of the nitrogen mustards that is still used for military purposes. It is the principal representative of the nitrogen mustards because its vesicant properties are almost equal to those of ] and thus the analogy between the two types of mustard is the strongest.<ref name=niosh>. Emergency Response Safety and Health Database. ]. August 22, 2008. Accessed April 10, 2009.</ref> As a vesicant the use and production is strongly restricted within the ] where it is classified as a ]. |
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'''2-Chloro-''N'',''N''-bis(2-chloroethyl)ethanamine''', also known as '''trichlormethine''', '''tris(2-chloroethyl)amine''' is the ] with the ] N(CH<sub>2</sub>CH<sub>2</sub>Cl)<sub>3</sub>. Often abbreviated HN3 or HN-3, it is a powerful ] and a ] used for ]. HN3 was the last of the nitrogen mustard agents developed. It was designed as a military agent and is the only one of the nitrogen mustards that is still used for military purposes. It is the principal representative of the nitrogen mustards because its vesicant properties are almost equal to those of ] and thus the analogy between the two types of mustard is the strongest.<ref name=niosh>. Emergency Response Safety and Health Database. ]. August 22, 2008. Accessed April 10, 2009.</ref> As a ] the use and production is strongly restricted within the ] where it is classified as a ]. |
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==Mode of action== |
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==Mode of action== |
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Nitrogen mustards react via an initial cyclization to the corresponding iminium salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize. |
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Nitrogen mustards react via an initial cyclization to the corresponding quaternary ] salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize. |
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==Applications== |
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==Applications== |
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HN-3 has found some applications in chemotherapy, e.g., for ], but it is mainly of interest for its military uses and is the only one of these agents that remains anywhere as a military agent. These agents are more immediately toxic than the ]s. |
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HN-3 has found some applications in chemotherapy, e.g., for ], and in some compound semiconductor research<ref>{{cite book|last=Benard|first=C.|title=Chemical Vapor Deposition|year=1997|publisher=The Electrochemical Society, INC|location=Pennington, NJ, USA|isbn=1-56677-178-1|pages=78}}</ref> but it is mainly of interest for its military uses and is the only one of these agents that remains anywhere as a military agent.{{Citation needed |reason=Specifically which militaries continue to stockpile HN3, and how do they use it (war, detection and protection, research, other)? |date=November 2019}} These agents are more immediately toxic than the ]s. |
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==Exposure== |
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==Exposure== |
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==See also== |
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==See also== |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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{{Chemical warfare}} |
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{{chemical warfare}} |
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{{Nitrogen mustards}} |
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