メチルビス(2-クロロエチル)アミン
クロルエタジン · 窒素マスタード · 2-クロロ-N-(2-クロロエチル)-N-メチルエタン-1-アミン · N,N-ビス(2-クロロエチル)-N-メチルアミン · N,N-ビス(2-クロロエチル)メタンアミン · メクロレタミン · ビス(2-クロロエチル)メチルアミン · メクロルエタミン
識別子と物理属性
| CAS No. | 51-75-2 |
|---|---|
| 分子式 | C5H11Cl2N |
| 平均分子量 | 156.05 g/mol |
| 単同位体質量 | 155.02685471 g/mol |
| SMILES | CN(CCCl)CCCl |
| InChIKey | HAWPXGHAZFHHAD-UHFFFAOYSA-N |
| PubChem CID | 4033 |
| ChEMBL | CHEMBL427 |
| ChEBI | CHEBI:28925 |
| EC No. | 200-120-5 |
| DTXSID | DTXSID2020975 |
| 現地名 | メチルビス(2-クロロエチル)アミン |
化学・物理的性質
| XLogP | 0.9 |
|---|---|
| 極性表面積 | 3.2 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 4 |
| 重原子数 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 43.7 |
| 物質分類 | Toxic Gases & Vapors -> Chemical WeaponsCarcinogens-> NIOSH Emergency Response Categories |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Boiling point |
| LogP（分配係数） | log Kow = 0.911.6 |
| 臭い | Faint odor of herring |
| 密度 | 1.118 at 77 °F (EPA, 1998) - Denser than waterwill sink1.118 @ 25 °C/4 °C1.118 @25 °Cd425 1.118 |
| Color/Form | Mobile liquidDark liquidLiquid, colorless/pale yellow when fresh |
| 溶解度 | Very solubleVery slightly soluble in watermiscible with dimethyl formamide, carbon disulfide, carbon tetrachloride, many organic solvents and oils3.34e+01 g/L |
| Human Drugs | Breast FeedingLactationMilk, HumanAntineoplastic AgentsAlkylating AgentsIrritantsEMA approved medicines: Human medicine (Orphan designations) |
| 沸点 | 189 °F at 18 mmHg (EPA, 1998)87°C at 1.80E+01 mm Hg87 °C @ 18 mm Hgbp18 87°bp10 75°bp5 64°bp2 59° |
| 融点 | -76 °F (EPA, 1998)-60 °C108 - 111 °C-60° |
| 蒸気密度 | 5.9 (Air=1)0.17 mm at 25°C |
| 屈折率 | 1.5500 (estimate) |
| pKa（酸解離定数） | 6.40±0.30(Predicted) |
| 外観・状態 | HN-2 は、低濃度では石鹸臭があり、高濃度ではフルーティーな香りがします。 |
| 色 | 暗い液体 |
| ヘンリー定数 | 3.4×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| NISTの化学物質情報 | Bis(2-chloroethyl)methylamine(51-75-2) |
| EPAの化学物質情報 | Nitrogen mustard (HN-2) (51-75-2) |
化学的特性
Nitrogen mustard is a pale yellow, oily, mobile liquid with a faint odor of herring. Nitrogen mustards are colorless when pure but are typically a yellow to brown oily substance. Odors are variably described as; sweet, agreeable, slightly garlic- or mustard-like. NIOSH reports HN-2 as having “a fruity odor at high concentrations, and a soapy or fishy odor at low concentrations.
安全性と法規制
| GHS 分類 | DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]P203, P260, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P308+P316, P316, P317, P318, P320, P321, P330, P361+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Hazard Traits - CarcinogenicityDevelopmental ToxicityThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| その他の安全情報 | - Indoor Air: HN-2 can be released into indoor air as a liquid spray (aerosol) or as a vapor. |
| 火災危険 | For information on chemical warfare blister agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024) |
| 健康有害性 | For information on chemical warfare blister agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024) |
| 有害性の概要 | Nitrogen mustards are vesicants causing skin, eye, and respiratory tract injury. Although these agents cause cellular changes within several minutes of contact, the onset of pain and other clinical effects is delayed for hours. Nitrogen mustards are alkylating agents that may cause bone marrow suppression and neurologic toxicity. . . . Nitrogen mustards may decrease fertility. [ATSDR MMG] Danger of skin sensitizationGerm cell mutagens that have shown to increase the mutant frequency in the progeny of exposed mammals. [MAK] |
| 反応性グループ | Amines, Phosphines, and Pyridines |
| Explosion Hazards | - No immediate danger of fire or explosion. |
| Special Reports | DHHS/ATSDRMedical Management Guidelines for Blister Agents: Nitrogen Mustard (HN-1), Nitrogen Mustard (HN-2), Nitrogen Mustard (HN-3) (updated: 8/22/2003) Available from: http://www.atsdr.cdc.gov/MHMI/mmg164.html as of November 26, 2003. |
| Reactivity Profile | MECHLORETHAMINE is a chlorinated amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. |
用途
解説
アンモニアと塩素を水に溶かした場合に生じ、次亜塩素酸を遊離して殺菌・漂白作用を示す。
用途
軍用の化学製剤
説明
Nitrogen mustards are very potential chemical substances of yesteryears and produced during the 1920s and 1930s as chemical warfare weapons. They are vesicants (or blister agents) similar to the sulphur mustards. They smell fishy, musty, soapy, or fruity and are either in the form of an oily textured liquid or a vapour (the gaseous form of a liquid) or a solid. It is in liquid form at normal room temperature (70 F) with a clear, pale amber, or yellow colour. HN-1, HN-2, and HN-3 are the military designations of nitrogen mustard (for more data, refer to Muatars gas). Nitrogen mustards (HN-1, HN-2, HN-3) are colourless to yellow, oily liquids that evaporate very slowly. HN-1 has a faint fishy or musty odour. HN-2 has a soapy odour at low concentrations and a fruity odour at higher concentrations. HN-3 may smell like butter almond. Use of nitrogen mustards is very much restricted other than for chemical warfare. In fact, presently, its use has no records. HN-1 has been used to remove warts in the past, and HN-2 has been used sparingly in chemotherapy.
使用
Antineoplastic.
一般的な説明
Mobile liquid; faint odor of herring. Used as a drug for the treatment of cancer. Formerly used as a gas warfare agent.
製法・合成法
調製方法
The nitrogen mustards are tertiary amines in which the halogen atom and the amine portion have reactivities similar to those of alkyl halides and alkyl amines. They are oily liquids that have limited water solubility but form readily soluble hydrochlorides. They are prepared by the action of thionyl chloride on the appropriate alkanolamine. Many of the actions of the nitrogen mustards resemble those of ethyleneimine derivatives because they are transformed in aqueous solutions into the highly reactive ethylenimonium intermediates: these ions can readily react with a variety of organic compounds in vitro, especially with amino, sulfhydro, and carboxyl groups of proteins and phosphate groups in nucleic acid, and therefore can alkylate biologically important macromolecules.