Nitrogen mustard

Information about Nitrogen mustard

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HN1 (bis(2-chloroethyl)ethylamine)
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HN2 (bis(2-chloroethyl)methylamine)
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HN3 (tris(2-chloroethyl)amine)
The nitrogen mustards are cytotoxic chemotherapy agents similar to mustard gas. Although their common use is medicinal, in principle these compounds may also be used for chemical warfare purposes.

The prototype nitrogen mustard drug is mustine which is no longer commonly in use but was the first drug to be used as an anticancer chemotherapeutic. It is a schedule 1 substance in the Chemical Weapons Convention. Other nitrogen mustards include cyclophosphamide, chlorambucil, uramustine and melphalan.

Nitrogen mustards are nonspecific DNA alkylating agents, because they form cyclic ammonium ions by attack of nitrogen on the organochloride center (see Sulfur mustard#Chemistry). The effects are radiomimetic, i.e. the DNA damage is similar to that which is seen when genetic material is exposed to radiation.

Examples of nitrogen mustards that can be used for chemical warfare purposes and their military weapon designations include: Several nations stock-piled large amounts of munitions containing nitrogen mustard gas during the Second World War, but none were used in combat. As with all types of mustard gas, nitrogen mustard is a powerful and persistent blister agent.

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This article forms part of the series
Chemical warfare
Blood agents:Cyanogen chloride (CK) – Hydrogen cyanide (AC)
Blister agents:Lewisite (L) – Sulfur mustard gas (HD, H, HT, HL, HQ) – Nitrogen mustard gas (HN1, HN2, HN3)
Nerve agents:G-Agents: Tabun (GA) – Sarin (GB) – Soman (GD) – Cyclosarin (GF) – GV | V-Agents: VE – VG – VM – VX | Novichok agents
Pulmonary agents:Chlorine – Chloropicrin (PS) – Phosgene (CG) – Diphosgene (DP)
Incapacitating agents:Agent 15 (BZ) – KOLOKOL-1
Riot control agents:Pepper spray (OC) – CS gas – CN gas (mace) – CR gas
 •  • [ e]
Chemotherapy is the use of chemical substances to treat disease. In its modern-day use, it refers to cytotoxic drugs used to treat cancer or the combination of these drugs into a standardized treatment regimen.
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The sulfur mustards, of which mustard gas is a member, are a class of related cytotoxic, vesicant chemical warfare agents with the ability to form large blisters on exposed skin.
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Chemical warfare is warfare (and associated military operations) using the toxic properties of chemical substances to kill, injure or incapacitate an enemy.
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Mechlorethamine also known as chlormethine, mustine, nitrogen mustard and HN2 and sold under the brand name Mustargen, is the prototype anticancer chemotherapeutic drug.
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Schedule 1 substances, in the sense of the Chemical Weapons Convention, are chemicals which can either be used as chemical weapons themselves or used in the manufacture of chemical weapons and which have no, or very limited, uses outside of chemical warfare.
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Chemical Weapons Convention (CWC) is an arms control agreement which outlaws the production, stockpiling and use of chemical weapons. Its full name is the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their
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Cyclophosphamide (the generic name for Cytoxan, Neosar), also known as cytophosphane, is a nitrogen mustard alkylating agent, used to treat various types of cancer and some autoimmune disorders.
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Chlorambucil (marketed as Leukeran by GlaxoSmithKline) is a chemotherapy drug that has been mainly used in the treatment of chronic lymphocytic leukemia. It is a nitrogen mustard alkylating agent and can be given orally.
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Uracil mustard or uramustine is a chemotherapy drug which belongs to the class of alkylating agents. It is used in lymphatic malignancies such as non-Hodgkin's lymphoma.
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Melphalan hydrochloride (trade name Alkeran) is a chemotherapy drug belonging to the class of nitrogen mustard alkylating agents. It is used primarily to treat multiple myeloma and ovarian cancer, and occasionally malignant melanoma.
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Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene (or their equivalents).
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Bis(2-chloroethyl)ethylamine is the organic compound with the formula C2H5N(CH2CH2Cl)2. Often abbreviated HN1, it is a powerful vesicant and a so-called nitrogen mustard gas (it is not a gas) used for chemical warfare.
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Mechlorethamine also known as chlormethine, mustine, nitrogen mustard and HN2 and sold under the brand name Mustargen, is the prototype anticancer chemotherapeutic drug.
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Tris(2-chloroethyl)ethylamine is the organic compound with the formula N(CH2CH2Cl)3. Often abbreviated HN3, it is a powerful blister agent and a so-called nitrogen mustard gas (it is not a gas) used for chemical warfare.
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The sulfur mustards, of which mustard gas is a member, are a class of related cytotoxic, vesicant chemical warfare agents with the ability to form large blisters on exposed skin.
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Allied powers:
 Soviet Union
 United States
 United Kingdom
 China
 France
...et al. Axis powers:
 Germany
 Japan
 Italy
...et al.
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blister agent (also known as a vesicant) is a chemical compound that causes severe skin, eye and mucosal pain and irritation. They are named for their ability to cause large, painful water blisters on the bodies of those affected.
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Chemical warfare is warfare (and associated military operations) using the toxic properties of chemical substances to kill, injure or incapacitate an enemy.
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A blood agent or cyanogen agent is a chemical compound, carried by the blood for distribution through the body. Blood agents may contain the cyanide group, which can inactivate the energy-producing cytochrome oxidase enzymes of cells in the body.
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Cyanogen chloride is a chemical compound with the formula CNCl. This linear triatomic pseudohalogen is an easily condensed colorless gas. More commonly enountered in the laboratory is the related species cyanogen bromide, a room temperature solid, which is widely used in
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Hydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid. Hydrogen cyanide is a colorless, very poisonous, and highly volatile liquid that boils slightly above room temperature at 26 °C (78.8 °F).
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blister agent (also known as a vesicant) is a chemical compound that causes severe skin, eye and mucosal pain and irritation. They are named for their ability to cause large, painful water blisters on the bodies of those affected.
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Lewisite is a chemical compound from a chemical family called arsines. While it is a colorless and odorless liquid when pure it is usually found as an oily, brown liquid with a distinct odor similar to geraniums.
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The sulfur mustards, of which mustard gas is a member, are a class of related cytotoxic, vesicant chemical warfare agents with the ability to form large blisters on exposed skin.
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Nerve Agents (also known as nerve gases, though these chemicals are liquid at room temperature) are a class of phosphorus-containing organic chemicals (organophosphates) that disrupt the mechanism by which nerves transfer messages to organs.
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Tabun or GA (Ethyl N,N-dimethylphosphoramidocyanidate) is an extremely toxic substance that has the potential to be one of the world's most dangerous military weapons. It is a clear, colorless, tasteless liquid with a faint fruity odor.
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Sarin, also known by its NATO designation of GB, (O-Isopropyl methylphosphonofluoridate) is an extremely toxic substance whose sole application is as a nerve agent.
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Soman, also known by its NATO designation GD (O-Pinacolyl methylphosphonofluoridate) is an extremely toxic substance whose sole application is as one of the world's most dangerous military weapons.
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Cyclosarin or GF (cyclohexyl methylphosphonofluoridate) is an extremely toxic substance that is one of the world's most dangerous weapons of war. It is a member of the G-series
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GV (P-[2-(dimethylamino)ethyl]-N,N-dimethylphosphonamidic fluoride) is an organophosphate nerve agent. GV is a part of a new series of nerve agents with properties similar to both the "G-series" and "V-series"

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