51-75-2 Usage
Description
Chlormethine, also known as HN-2, is a nitrogen mustard compound with a fishy odor and lachrymatory properties. It is a pale yellow, oily, mobile liquid at room temperature and is similar in structure to mustard gas, with the sulfur replaced by an amino nitrogen. Chlormethine was initially produced as a chemical warfare agent during the 1920s and 1930s but has since been used sparingly in chemotherapy and as an antineoplastic agent.
Uses
Used in Anticancer Applications:
Chlormethine is used as an antineoplastic agent for the treatment of cancer. It has been employed in chemotherapy, particularly against solid malignancies, due to its ability to interfere with cell division and DNA synthesis in cancer cells.
Used in Chemical Warfare:
Chlormethine, under the military designation HN-2, was formerly used as a gas warfare agent. However, its use in this context is now highly restricted, and there are no current records of its use for this purpose.
Used in Pharmaceutical Industry:
Chlormethine is used in the pharmaceutical industry under the brand name Mustargen (Ovation) as a drug for the treatment of cancer. Its application in this industry is focused on its antineoplastic properties, which make it a valuable compound in the fight against various types of cancer.
Production Methods
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.
Reactivity Profile
Chlormethine 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.
Hazard
Strong irritant to tissues, lachrymatory.
Probable carcinogen.
Health Hazard
Toxic doses as low as 400 mg/kg have been reported in humans. Blood clots may occur at site of intravenous injection and tissue damage if outside vein. Powerful vesicant (causes blisters) when it contacts skin, mucous membranes, or eyes. Delayed toxicity -- missed menstrual periods, alopecia (hair loss), hearing loss, tinnitus (ringing in ears), jaundice, impaired spermatogenesis and germinal aplasia, swelling, and hypersensitivity. May damage fetus in pregnant women.
Fire Hazard
Undiluted liquid decomposes on standing.
Safety Profile
Confirmed human carcinogenproducing skin tumors by skin contact. Experimentalcarcinogenic, tumorigenic, and neoplastigenic data. Adeadly poison by inhalation, ingestion, skin contact, andmost other routes. Experimental teratogenic andreproductive eff
Potential Exposure
Drug used in treatment of cancer.
Exposure to nitrogen mustard damages the eyes, skin, and
respiratory tract and suppresses the immune system.
Although the nitrogen mustards cause cellular changes
within minutes of contact, the onset of pain and other
symptoms is delayed. Exposure to large amounts can be
fatal. Sulfur mustards were formerly used as a gas
warfare agent. Nitrogen mustards have not previously been
used in warfare
Shipping
UN2810 Toxic liquids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. Military driver shall be given full and
complete information regarding shipment and conditions in
case of emergency. AR 50-6 deals specifically with the
shipment of chemical agents. Shipments of agent will be
escorted in accordance with AR 740-32
Incompatibilities
HN-2 is not stable except as dry crystals.
Polymerization of HN-2 results in components that present
an explosion hazard in open air. Avoid contact or
contamination with oxidizers e.g., nitrates, oxidizing acids;
chlorine bleaches pool chlorine); which may result in ignition. Unstable in the presence of light and heat and forms
dimers at temperatures above 50C. Corrosive to ferrous
alloys beginning @ 65C. Polymerizes slowly, so munitions would be effective for several years. Heated to
decomposition emits hydrogen chloride and nitrogen oxide.
Contact with metals may evolve flammable hydrogen
gas. Note: Chlorinating agents destroy nitrogen mustards. Dry chlorinated lime and chloramines with a high
content of active chlorine vigorously chlorinate nitrogen
mustards to the carbon chain, giving low toxicity products.
In the presence of water this interaction proceeds less
actively. They are rapidly oxidized by peracids in aqueous
solution at weakly alkaline pH. In acid solution the
oxidation is much slower.An amine and a chemical base: will neutralize acids to
form salts plus water with an exothermic reaction. 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, nitrides, alkali metals, and sulfides
Waste Disposal
It is inappropriate and possibly dangerous to the environment to dispose of expired or
waste drugs and pharmaceuticals by flushing them down
the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed
with wet cat litter or coffee grounds, double-bagged in
plastic, discard in trash. Larger quantities shall carefully
take into consideration applicable DEA, EPA, and FDA
regulations. If possible return the pharmaceutical to the
manufacturer for proper disposal being careful to properly
label and securely package the material. Alternatively, the
waste pharmaceutical shall be labeled, securely packaged,
and transported by a state licensed medical waste contractor
to dispose by burial in a licensed hazardous or toxic waste
landfill or incinerator
Check Digit Verification of cas no
The CAS Registry Mumber 51-75-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 51-75:
(4*5)+(3*1)+(2*7)+(1*5)=42
42 % 10 = 2
So 51-75-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H11Cl2N/c1-4(6)8(3)5(2)7/h4-5H,1-3H3
51-75-2Relevant articles and documents
Synthesis and cytotoxicity of pyridine and quinoline oxorhenium(V) complexes with tridentate (NS2, S3)/monodentate (S) coordination
Segal,Zablotskaya,Kniess,Shestakova
, p. 296 - 300 (2012)
New oxorhenium complexes with tridentate 3-thia- and 3-methylazapentane-1, 5-dithiolate and monodentate pyridine and quinoline derivatives have been synthesized. As a result of investigation of biological activity a high cytotoxicity was found for the synthesized complexes in relation to tumor cells. The specificity of the 2-pyridylthiolato[3-(N-methyl)azapentane-1,5-dithiolato] oxorhenium(V) cytotoxic action towards cells of mouse hepatoma MG-22A on a background of low acute toxicity was established.
Utilisation of new NiSNS pincer complexes in paraffin oxidation
Soobramoney, Lynette,Bala, Muhammad D.,Friedrich, Holger B.
, p. 97 - 105 (2018/05/09)
Two series of closely related SNS pincer ligands (L) were synthesised with the major structural variation on the nitrogen backbone containing either the methyl [L = (RSCH2CH2)2NMe: where R = Me (1), Et (2), Bu (3)] or the phenyl [L = (RSCH2CH2)2NPh: where R = Me (4), Et (5), Cy (6)] functional group. When ligands 1–3 were complexed to Ni by reaction with Ni(DME)Cl2 (DME = dimethoxyethane), they respectively yielded three new cationic dimeric [LNi(μ-Cl)3NiL]+ complexes (7–9), whilst ligands 4–6 on reaction with Ni(PPh3)2Br2 respectively yielded neutral mononuclear (LNiBr2) complexes 10–12. All the new compounds were characterised by IR, HRMS, elemental analysis and in addition, single crystal X-ray diffraction for complexes 9–12. X-ray structural data of 9 revealed an unusual three chlorido-bridged Ni dimer with the SNS ligand coordinated in a facial binding mode to the two pseudo-octahedral Ni centres. Molecular structures of complexes 10, 11 and 12 each displayed five-coordinate distorted trigonal bipyramidal geometry around the nickel(II) metal centres. When utilised as catalysts in the tert-butyl hydroperoxide oxidation of n-octane, all the complexes showed activity to mainly products of internal carbon activation (octanones and secondary octanols) with 11 as the most active (10% total substrate to oxygenates yield), whereas 10 was the least active, but most selective towards alcohols (alcohol/ketone = 2.13).
THERAPEUTIC FOR HEPATIC CANCER
-
, (2011/02/18)
A novel pharmaceutical composition for treating or preventing hepatocellular carcinoma and a method of treatment are provided. A pharmaceutical composition for treating or preventing liver cancer is obtained by combining a chemotherapeutic agent with an anti-glypican 3 antibody. Also disclosed is a pharmaceutical composition for treating or preventing liver cancer which comprises as an active ingredient an anti-glypican 3 antibody for use in combination with a chemotherapeutic agent, or which comprises as an active ingredient a chemotherapeutic agent for use in combination with an anti-glypican 3 antibody. Using the chemotherapeutic agent and the anti-glypican 3 antibody in combination yields better therapeutic effects than using the chemotherapeutic agent alone, and mitigates side effects that arise from liver cancer treatment with the chemotherapeutic agent.