Mechlorethamine oxide hydrochloride
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Mechlorethamine oxide hydrochloride
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CAS No:
302-70-5
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Formula:
C5H11Cl2NO.ClH
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Chemical Name:
Mechlorethamine oxide hydrochloride
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Synonyms:
Ethanamine,2-chloro-N-(2-chloroethyl)-N-methyl-,N-oxide,hydrochloride (1:1);Diethylamine,2,2′-dichloro-N-methyl-,N-oxide,hydrochloride;Ethanamine,2-chloro-N-(2-chloroethyl)-N-methyl-,N-oxide,hydrochloride;Diethylamine,2,2′-dichloro-N-methyl-,N-oxide,compd. with hydrochloric acid;2,2′-Dichloro-N-methyldiethylamine N-oxide hydrochloride;Mechlorethamine oxide hydrochloride;Methylbis(β-chloroethyl)amine N-oxide hydrochloride;N-Methylbis(2-chloroethyl)amine N-oxide hydrochloride;Mitomen;Mustron;Nitromin;Nitromin hydrochloride;Nitrogen mustard N-oxide hydrochloride;N-Methyl-2,2′-dichlorodiethylamine N-oxide hydrochloride;Methyldi(2-chloroethyl)amine N-oxide hydrochloride;Methylbis(β-chloroethyl)amine oxide hydrochloride
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CAS No:
Description
Nitrogen mustard N-oxide hydrochloride is a nitrogen mustard.|Mechlorethamine Oxide Hydrochloride is a nitrogen mustard alkylating agent that causes DNA cross linkages. It is a known carcinogen especially in mice. (NCI)|A biologic alkylating agent that exerts its cytotoxic effects by forming DNA ADDUCTS and DNA interstrand crosslinks, thereby inhibiting rapidly proliferating cells. The hydrochloride is an antineoplastic agent used to treat HODGKIN DISEASE and LYMPHOMA.
Mechlorethamine oxide hydrochloride Basic Attributes
208.51400
206.99800
009L92D6OC
10107
DTXSID0023375
C628
Prisms from acetone|COLORLESS CRYSTALS
2921199090
Characteristics
29.43000
2.23130
109-110 °C
FREELY SOL IN ETHANOL; SLIGHTLY SOL IN BENZENE, ETHER
LD50 oral in rat: 60mg/kg
ODORLESS
HYDROLYZES IN ALKALINE SOLN (PH 8), MUCH MORE SLOWLY THAN DOES FREE BASE|READILY REDUCED, EG, RELEASES IODINE FROM POTASSIUM IODIDE|Mol wt: 172; Soluble in water; sparingly soluble in benzene and ether /Nitrogen mustard n-oxide/
Safety Information
II
6.1(a)
UN 3249
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Reactivity: Nitrogen Vesicants tend to polymerize. Polymerization may generate enough heat to cause an explosion. In addition, polymerized components may present an explosion hazard. Lack of solubility inhibits hydrolysis of Nitrogen Vesicants. /Vesicants - Nitrogen Based/
Personal Protective Requirements: Nitrogen Vesicants pose both a severe respiratory and severe contact hazard. Wear appropriate fully encapsulating protective gear with positive pressure self contained breathing apparatus (SCBA). Structural firefighters' protective clothing is recommended for fire situations only; it is not effective in spill or release events. Solid agents pose a less significant vapor hazard but a much more significant contact hazard. If solid agents have been released, dust control during windy conditions will be essential. /Vesicants- Nitrogen Based/
Fire: Vesicants may be volatilized during a fire or be spread by efforts to extinguish the fire. Agents may be decomposed by heat to produce other toxic and/or corrosive gases. In addition, Nitrogen Vesicants may react with steam or water during a fire to produce toxic and/or corrosive vapors. Hydrogen produced by the action of the corrosive vapors on metals or other corrodible materials may be present. Nitrogen Vesicants tend to polymerize and the polymerization products may present an explosion hazard. /Vesicants - Nitrogen Based/
Protection: Evacuation: Immediately isolate an area around any liquid or solid contamination for at least 400 feet in all directions. If possible, identify the agent and develop a downwind hazard diagram (see Table 3.2). Adjust the initial isolation distance as appropriate. Based on the type of release, amount of material aerosolized, persistence of the agent and local conditions (e.g., weather, population density, time of day), shelter in place until the initial cloud passes may be the most appropriate course of action since timely evacuation of the threatened downwind population may not be possible. Depending on the persistence of the agent and the potential for condensation of agent from the cloud, evacuation of the threatened population after passage of the initial cloud may be appropriate. /Vesicants- Nitrogen Based/
Decontamination: Vapor: Casualties/personnel: Speed in decontamination is absolutely essential. Immediately wash skin and clothes with a bleach solution that is no less than one part household bleach in nine parts water. Rinse with copious amounts of water. To be effective, decontamination must be completed within one minute of exposure. In all cases, clothing should be removed because it may contain "trapped" vapor. Small Areas: Decontaminate with copious amounts of full strength household bleach. Removal of porous material, including painted surfaces, that may have absorbed Nitrogen Vesicant vapor may be required as these materials could continue to re release vapor after exposure has ceased. /Vesicants- Nitrogen Based/|Decontamination: Liquid: Casualties/personnel: Speed in decontamination is absolutely essential. Remove contaminated clothing immediately. Remove as much of the agent from the skin as fast as possible without spreading the material. Immediately wash skin and clothes with a bleach solution that is no less than one part household bleach in nine parts water. Rinse with copious amounts of water. To be effective, decontamination must be completed within one minute of exposure. However, to prevent systemic toxicity, decontamination should be done as late as 2 or 3 hours after exposure even if it increases the severity of the local reaction. In all cases, clothing should be removed because it may contain "trapped" liquid or vapor. Small Areas: Puddles of liquid must be contained by covering with vermiculite, diatomaceous earth, clay, fine sand, sponges, paper towels or cloth towels. Remove all material and place in a container. Decontaminate the area with copious amounts of household bleach. A 10 weight percent HTH/water slurry may be substituted for the bleach solution. Removal of porous material, including painted surfaces, that may have absorbed Vesicant liquid may be required as these materials could continue to re-release vapor after exposure has ceased. Surfaces contaminated with Vesicants then only rinsed may still evolve sufficient agent vapor to produce a physiological response. /Vesicants- Nitrogen Based/|Decontamination: Solid: Casualties/personnel: Speed in decontamination is absolutely essential. Remove contaminated clothing immediately. Remove as much of the agent from the skin as fast as possible without spreading the material. Immediately wash skin with a bleach solution that is no less than one part household bleach in nine parts water. Rinse with copious amounts of water. To be effective, decontamination must be completed within one minute of exposure. However, to prevent systemic toxicity, decontamination should be done as late as 2 or 3 hours after exposure even if it increases the severity of the local reaction. Remove all clothing from casualties regardless of apparent contamination. Extreme care must be exercised when dealing with solids as agents may adhere to the skin or clothing and present a contact and inhalation hazard later. Immediately wash clothes with a bleach solution that is no less than one part household bleach in nine parts water. Rinse with copious amounts of water. Small Areas: Consolidate as much material as possible and place into containers. In heavily contaminated areas, employ vacuum devices equipped with High Efficiency Particulate Air (HEPA) filters to remove as much agent as possible. Decontaminate the area with copious amounts of full strength household bleach. A 10 weight percent HTH pool bleach/water slurry may be substituted for the bleach solution. /Vesicants- Nitrogen Based/
Toxicity
Toxicology Effects: Vesicants affect both exterior and interior parts of the body. Vesicants cause inflammation, blisters, and general destruction of tissues. Vapors have a greater impact on moist areas of the body. Eyes are especially susceptible to vesicants. Inhalation of Vesicants can cause lung membranes to swell and become filled with liquid (pulmonary edema). Death may result from lack of oxygen. Vesicants are also systemic agents and readily pass through the skin to affect susceptible tissue including those that produce blood. Nitrogen Vesicants should be considered carcinogenic. Pathways: Vesicants are hazardous through inhalation, skin and eye exposure, ingestion, and abraded skin (e.g., breaks in the skin or penetration of skin by debris). /Vesicants- Nitrogen Based/|Latency Period: Tissue damage occurs within minutes of exposure to Nitrogen Vesicants, but clinical effects may not appear for up to 24 hours. Eye irritation may develop immediately. Pulmonary edema caused by inhalation of the agent vapor may be delayed for several hours. /Vesicants - Nitrogen Based/
COMBINED INFUSION OF NITROGEN MUSTARD N-OXIDE (10 OR 20 MG/KG) INTO HEPATIC ARTERY ALONG WITH SYSTEMIC ADMIN OF CYSTEINE (500 MG/KG) IN SARCOMA BEARING RATS, CONTROLLED TUMOR GROWTH IN LIVER. ALL RATS RECEIVING ONLY NITROGEN MUSTARD N-OXIDE BY INFUSION INTO HEPATIC ARTERY DIED.
Exposure Hazards: Skin impacts from Nitrogen Vesicant vapor occur at concentrations as low as 30 ppm (10 minute exposure). Eye impacts from Nitrogen Vesicant vapor occur at concentrations as low as 1 ppm (10 minute exposure). LC50s for inhalation of Nitrogen Vesicants are as low as 18 ppm (10 minute exposure). LD50s for skin exposure to liquid Nitrogen Vesicants are as low as 0.7 gm per individual. /Vesicants- Nitrogen Based/
Since the substance is used only as an antineoplastic agent, health professionals (eg, pharmacists, nurses, and physicians) involved in cancer chemotherapy are the principal personnel who potentially may be exposed. Exposure may occur during drug preparation, administration, or cleanup.
Drug Information
Alkylating Agents; Antineoplastic Agents, Alkylating; Chemical Warfare Agents; Irritants|EXPTL USE: STUDIES ON IMMUNOSUPPRESSIVE EFFECTS OF ... /NITROGEN MUSTARD N-OXIDE HYDROCHLORIDE/ IN TREATMENT OF SUCH DISEASES AS NEPHROTIC SYNDROME & IN SKIN GRAFTING HAVE BEEN MADE IN /JAPAN/ ...|EXPTL USE MEDICATION (VET): WALKER TUMOR BEARING RATS SUBJECTED TO SC FERRITE MAGNET RING (500 G) IMPLANTATION & GIVEN IP NITROMIN WITH IRON COLLOID WHICH EFFECTIVELY INHIBITED TUMOR GROWTH.|IN JAPAN HN2 N-OXIDE HYDROCHLORIDE HAS BEEN USED IN HUMAN MEDICINE ... FOR TREATMENT OF LYMPHOMAS & OAT-CELL CARCINOMAS OF LUNG. IT IS ADMIN ORALLY IN DOSES OF 0.5 MG/KG BODY WT DAILY FOR 5-12 DAYS OR IV IN DOSES OF 0.5-2 MG/KG BODY WT DAILY.|ANTINEOPLASTIC AGENT (NON-USA USE)
A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)|Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases. (See all compounds classified as Alkylating Agents.)|Chemicals that are used to cause the disturbance, disease, or death of humans during WARFARE. (See all compounds classified as Chemical Warfare Agents.)|Drugs that act locally on cutaneous or mucosal surfaces to produce inflammation; those that cause redness due to hyperemia are rubefacients; those that raise blisters are vesicants and those that penetrate sebaceous glands and cause abscesses are pustulants; tear gases and mustard gases are also irritants. (See all compounds classified as Irritants.)
After iv injection of 5 mg/kg body wt (14)C-labeled-methyl nitrogen mustard N-oxide in dogs ... no activity ... in blood after 1 hr in urine, highest level of radioactivity was found between 5 & 20 min after injection & had declined to 0 after 4 hr.
First Aid: Signs & Symptoms: Mild vapor exposure may not produce skin lesions. There is an asymptomatic latent period (4 to 24 hours) followed by inflammation and redness of the skin progressing to blisters. Eye impacts, including irritation, tearing, and sensitivity to light may appear immediately. There may also be inflammation of the eyes. Larger amounts of vapor cause swelling of the eyelids. Pain in the eyes may cause spasms and eventually cause the eyes to close. Upper respiratory signs vary with the amount of exposure and include nasal irritation, scratchy throat, laryngitis, and a feeling of shortness of breath. /Vesicants - Nitrogen Based/|Patient Management: Immediate decontamination of any exposure is essential. If the casualty has been exposed to Nitrogen Vesicant liquid, then decontamination should be done as late as 2 or 3 hours after exposure even if it increases the severity of the local reaction. This must be done to prevent systemic toxicity. Otherwise, treatment consists of symptomatic management of lesions. Asymptomatic individuals suspected of exposure to vesicants should be kept under observation for at least 8 hours. /Vesicants - Nitrogen Based/
Suspected carcinogen with experimental tumorigenic data. Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Mutation data reported.
Bis(2-chloroethyl)methylamine
Mechlorethamine oxide hydrochloride Use and Manufacturing
Prepn by treating 2,2'-dichloro-N-methyldiethylamine with hydrogen peroxide and acetic anhydride in ether, followed by shaking with 10% hydrochloric acid: Alko et al, J Pharm Soc Japan 72: 1297 (1952, English text), Chemical Abstract 47: 1289 (1953).
Antineoplastic agent (non-USA use)|MEDICATION|MEDICATION (VET)
NOT PRODUCED COMMERCIALLY IN USA
/AS ANTINEOPLASTIC AGENT/ ... AVAIL IN AUSTRIA & JAPAN IN FORM OF TABLETS CONTAINING 5 MG ACTIVE INGREDIENT & IN AMPULES FOR IV INJECTION CONTAINING 25 & 50 MG.
... IT HAS BEEN TESTED FOR USE AS ... INSECT STERILANT ...
Computed Properties
Molecular Weight:208.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:206.998447
Monoisotopic Mass:206.998447
Topological Polar Surface Area:18.1
Heavy Atom Count:10
Complexity:73.4
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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Mechlorethamine oxide hydrochloride
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