Nitrogen Mustards
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Nitrogen Mustards
Nitrogen mustards (NMs) are cytotoxic organic compounds with the bis(2-chloroethyl)amino ((ClC2H4)2NR) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of cancer. Nitrogen mustards are nonspecific DNA alkylating agents. Name Nitrogen mustards are not related to the mustard plant or its pungent essence, allyl isothiocyanate; the name comes from the pungent smell of chemical weapons preparations. Chemical warfare During World War II, nitrogen mustards were studied at the Yale School of Medicine by Alfred Gilman and Louis Goodman, and in December 1942, they started classified human clinical trials of nitrogen mustards for the treatment of lymphoma. In early December of 1943, an incident during the air raid on Bari, Italy, led to the release of mustard gas that affected several hundred soldiers and civilians. Medical examination of the survivors showed a decreased number of lymphocytes. After Wo ...
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Chemotherapy
Chemotherapy (often abbreviated chemo, sometimes CTX and CTx) is the type of cancer treatment that uses one or more anti-cancer drugs (list of chemotherapeutic agents, chemotherapeutic agents or alkylating agents) in a standard chemotherapy regimen, regimen. Chemotherapy may be given with a cure, curative intent (which almost always involves combinations of drugs), or it may aim only to prolong life or to Palliative care, reduce symptoms (Palliative care, palliative chemotherapy). Chemotherapy is one of the major categories of the medical discipline specifically devoted to pharmacotherapy for cancer, which is called ''oncology#Specialties, medical oncology''. The term ''chemotherapy'' now means the non-specific use of intracellular poisons to inhibit mitosis (cell division) or to induce DNA damage (naturally occurring), DNA damage (so that DNA repair can augment chemotherapy). This meaning excludes the more-selective agents that block extracellular signals (signal transduction) ...
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Mazapertine
Mazapertine (RWJ-37796) is an antipsychotic agent that was developed by Johnson & Johnson but never marketed. It exerts its pharmacological effect through affinity for dopamine D2, serotonin 5-HT1A, and α1-adrenergic receptors. Mazapertine is safe and well tolerated when administered orally. Analogs of mazapertine with conformational restriction have been prepared and have greater affinity for the 5-HT1A receptor. Synthesis The laboratory synthesis of mazapertine has been reported.Allen B. Reitz, (1996 to Ortho McNeil Pharmaceutical Inc) It begins with alkylation of 2-nitrophenol (1) with isopropyl bromide to give 2-isopropoxynitrobenzene (2). Catalytic hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ... of nitro group gives 2-isopropoxyaniline (3). Intermol ...
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Piperazine
Piperazine () is an organic compound with the formula . In term of its structure, it can be described as cyclohexane with the 1- and 4-CH2 groups replaced by NH. Piperazine exists as deliquescent solid with a saline taste. Piperazine is freely soluble in water and ethylene glycol, but poorly soluble in diethyl ether. Piperazine is commonly available industrially is as the hexahydrate, , which melts at 44 °C and boils at 125–130 °C.''The Merck index, 10th Ed.'' (1983), p. 1076, Rahway:Merck & Co. Substituted derivatives of piperazine are a broad class of chemical compounds. Many piperazines have useful pharmacological properties, prominent examples include viagra, ciprofloxacin, and ziprasidone. Origin and naming Piperazines were originally named because of their chemical similarity with piperidine, part of the structure of piperine in the black pepper plant (''Piper nigrum''). The -az- infix added to "piperazine" refers to the extra nitrogen atom, compared to piperidine. ...
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Tris(2-chloroethyl)amine
2-Chloro-''N'',''N''-bis(2-chloroethyl)ethanamine, also known as trichlormethine, tris(2-chloroethyl)amine is the organic compound with the formula N(CH2CH2Cl)3. Often abbreviated HN3 or HN-3, it is a powerful blister agent and a nitrogen mustard used for chemical warfare. 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 HD and thus the analogy between the two types of mustard is the strongest.NITROGEN MUSTARD HN-3
Emergency Response Safety and Health Database.

Bis(2-chloroethyl)methylamine
Chlormethine (INN, BAN), also known as mechlorethamine (USAN, USP), mustine, HN2, and (in post-Soviet states) embikhin (эмбихин), is a nitrogen mustard sold under the brand name Mustargen among others. It is the prototype of alkylating agents, a group of anticancer chemotherapeutic drugs. It works by binding to DNA, crosslinking two strands and preventing cell duplication. It binds to the N7 nitrogen on the DNA base guanine. As the chemical is a blister agent, its use is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance. Mechlorethamine belongs to the group of nitrogen mustard alkylating agents. Uses It has been derivatized into the estrogen analogue estramustine phosphate, used to treat prostate cancer. It can also be used in chemical warfare where it has the code-name HN2. This chemical is a form of nitrogen mustard gas and a powerful vesicant. Historically, some uses of mechlorethamine have included lymphoid ...
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Bis(2-chloroethyl)ethylamine
Bis(2-chloroethyl)ethylamine is the organic compound with the formula C2H5N(CH2CH2Cl)2. Often abbreviated HN1, it is a powerful vesicant and a nitrogen mustard gas. HN1 was developed in the 1920s and 1930s to remove warts and later as a military agent. Because of the latter use, it is a Schedule 1 chemical within the Chemical Weapons Convention and therefore use and production is strongly restricted. It has never been used in warfare.The Emergency Response Safety and Health Database: NITROGEN MUSTARD HN-1
National Institute for Occupational Safety and Health. Accessed March 19, 2009.
It is an oily liquid with a colorless to pale yellow appearance and a faint fishy or musty odor. HN1 is also an

Bendamustine
Bendamustine, sold under the brand name Treanda among others, is a chemotherapy medication used in the treatment of chronic lymphocytic leukemia (CLL), multiple myeloma, and non-Hodgkin's lymphoma. It is given by intravenous, injection into a vein. Common side effects include cytopenia, low blood cell counts, fever, nausea, diarrhea, loss of appetite, cough, and rash. Other severe side effects include allergic reactions and increased risk of infection. Use in pregnancy is known to harm the baby. Bendamustine is in the alkylating antineoplastic agent, alkylating agents family of medication. It works by interfering with the function of DNA and RNA. Bendamustine was approved for medical use in the United States in 2008. It is on the WHO Model List of Essential Medicines, World Health Organization's List of Essential Medicines. It was originally made from nitrogen mustard. Medical uses One combination for stage III/IV relapsed or refractory indolent lymphomas and mantle cell ...
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