55-86-7 Usage
Description
Nitrogen mustard (HN) was developed in three formulations: HN-1, HN-2, and HN-3. HN-1 was the first to be produced in the late 1920s and early 1930s. Originally, it was developed as a pharmaceutical and used to remove warts before it became a military agent. Agent H-2 was developed as a military agent and became a pharmaceutical. HN-3 was designed as a military mustard agent and is the only one that remains in military use. Therefore, this section will only cover the characteristics of HN-3 mustard agent. HN-3 is colorless to pale yellow with a butter-almond odor. The chemical formula for nitrogen mustard agent HN-3 is N(CH2CH2Cl)3. It will otherwise be ineffective against stopping the damage to the body.
Chemical Properties
Different sources of media describe the Chemical Properties of 55-86-7 differently. You can refer to the following data:
1. White Solid
2. Highly toxic white to yellowish crystalline
solid or powder. May be available as an unstable aqueous
solution. Fish-like odor.
Uses
Different sources of media describe the Uses of 55-86-7 differently. You can refer to the following data:
1. xanthine oxidase/dehydrogenase inhibitor
2. It has been used as an antineoplastic. A nitrogen mustard prepared by action of thionyl chloride on 2,2’(methylimino)-
diethanol in trichloroethylene.
3. Mechlorethamine hydrochloride USP (Mustargen)is used to treat Hodgkin’s disease; non-Hodgkin’s lymphomas; lymphosarcoma; cancer of breast, ovary, lung; neoplastic effusion.
Definition
ChEBI: The hydrochloride salt of mechlorethamine.
Indications
Different sources of media describe the Indications of 55-86-7 differently. You can refer to the following data:
1. Mechlorethamine (Mustargen) is a cytotoxic alkylating
agent. Topical application of freshly prepared aqueous
solutions are used in patients with early stages of cutaneous
T-cell lymphoma. A major disadvantage to the
use of this drug is the rapid induction of allergic contact
dermatitis in some patients.
2. Mechlorethamine (nitrogen mustard; Mustargen), a derivative
of the war gas sulfur mustard, is considered to
be the first modern anticancer drug. In the early 1940s it
was discovered to be effective in the treatment of human
lymphomas.
Biological Functions
Mechlorethamine is still used in regimens for cancers of the blood (e.g., Hodgkin's disease, chronic myelocytic, or chronic lymphocytic leukemia); fortunately, however, safer and still highly potent antineoplastic agents are now available.
General Description
Different sources of media describe the General Description of 55-86-7 differently. You can refer to the following data:
1. White to off-white crystals or powder with a fishy odor. Initial pH (2% aqueous solution) 3.0-4.0.
2. Mechlorethamine is available in 10-mg vials for intravenous(IV) administration in the treatment of Hodgkin’slymphoma. It is part of the MOPP regimen used in treatingthis condition, which is comprised of mechlorethamine,vincristine (Oncovin), procarbazine, and prednisone. Theagent is also used topically in the treatment of mycosis fungoides,a rare type of cancer but the most common type ofcutaneous T-cell lymphoma. Additional uses have includedtreatment of cancers that have resulted in pleural effusion.Although the compound is a potent alkylating agent, resistancemay develop as a result of increased inactivation bysulfhydryl containing proteins such as glutathione andincreased expression of DNA repair mechanisms. Adverseeffects include dose-limiting myelosuppression and nausea/vomiting. There is a significant risk of extravasationupon IV administration, and the agent may produce painat the injection site. Additional adverse effects include alopecia, azoospermia, amenorrhea, hyperuricemia, and anincreased risk of secondary cancers.
Air & Water Reactions
Hygroscopic. Water soluble.
Reactivity Profile
Dry crystals are stable at temperatures up to 104° F. Chlormethine hydrochloride is incompatible with strong oxidizing agents. .
Hazard
Highly toxic, vesicant, and strongly irritant
to mucous membranes.
Fire Hazard
Flash point data for Chlormethine hydrochloride are not available. Chlormethine hydrochloride is probably combustible.
Mechanism of action
Mechlorethamine in aqueous solution loses a chloride
atom and forms a cyclic ethylenimmonium ion.This
carbonium ion interacts with nucleophilic groups, such
as the N7 and O6 of guanine, and leads to an interstrand
cross-linking of DNA. Although there is great variation
among normal and tumor tissues in their sensitivity to
mechlorethamine, the drug is generally more toxic to
proliferating cells than to resting or plateau cells.
Mechlorethamine has a chemical and biological half-life
in plasma of less than 10 minutes after intravenous injection.
Little or no intact drug is excreted in urine.
The major indication for mechlorethamine is
Hodgkin’s disease; the drug is given in the MOPP regimen. Other less reactive nitrogen
mustards are now preferred for the treatment of non-
Hodgkin’s lymphomas, leukemias, and various solid
tumors.
Clinical Use
Mechlorethamine is the only aliphatic nitrogen mustard currently on the U.S. market. Its use is limited by extremely high reactivity, which leads to rapid and nonspecific alkylation of cellular nucleophiles and excessive toxicity. It is a severe vesicant, and if accidental skin contact occurs, the drug must be inactivated with 2% sodium thiosulfate (Na2S2O3) solution.
Side effects
The dose-limiting toxicity of mechlorethamine is
myelosuppression; maximal leukopenia and thrombocytopenia
occur 10 to 14 days after drug administration,
and recovery is generally complete at 21 to 28 days.
Lymphopenia and immunosuppression may lead to activation
of latent herpes zoster infections, especially in
patients with lymphomas. Mechlorethamine will affect
rapidly proliferating normal tissues and cause alopecia,
diarrhea, and oral ulcerations. Nausea and vomiting may
occur 1 to 2 hours after injection and can last up to 24
hours. Since mechlorethamine is a potent blistering
agent, care should be taken to avoid extravasation into
subcutaneous tissues or even spillage onto the skin.
Reproductive toxicity includes amenorrhea and inhibition
of oogenesis and spermatogenesis. About half of
premenopausal women and almost all men treated for 6
months with MOPP chemotherapy become permanently
infertile. The drug is teratogenic and carcinogenic
in experimental animals.
Safety Profile
Confirmed carcinogen withexperimental carcinogenic, neoplastigenic, andtumorigenic data. Deadly poison by ingestion,intravenous, subcutaneous, intraperitoneal, and parenteralroutes. Experimental teratogenic and reproductive effects.Human systemic eff
Synthesis
Mechlorethamine, bis-(2-chloroethyl)methylamine (30.2.1.2), is made
by reacting methylamine with ethylene oxide, forming bis-(2-hydroxyethyl)methylamine
(30.2.1.1), which upon reaction with thionyl chloride turns into the desired mechlorethamine.
Carcinogenicity
Nitrogen mustard hydrochloride is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. In the literature, the names
“nitrogen mustard” and “nitrogen mustard hydrochloride” are used interchangeably. Only nitrogen mustard hydrochloride is produced commercially, so it is assumed that nitrogen mustard hydrochloride was used in all cancer studies in animals reported below.
Shipping
UN2928 Toxic solids, corrosive, organic, n.o.s.,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials,
8-Corrosive material, Technical Name Required. UN2811
Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels:
6.1-Poisonous materials, Technical Name Required.
Waste Disposal
It is not appropriate to dispose
of expired or waste product such as lab chemicals by
flushing them down the toilet or discarding them to the
trash. Larger quantities shall carefully take into consideration
applicable EPA, and FDA regulations. If possible
return the lab chemicals to the manufacturer for proper disposal
being careful to properly label and securely package
the material. Alternatively, the waste lab chemicals 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 55-86-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 5 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 55-86:
(4*5)+(3*5)+(2*8)+(1*6)=57
57 % 10 = 7
So 55-86-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H11Cl2N.ClH/c6-3-1-5(8)2-4-7;/h5H,1-4,8H2;1H
55-86-7Relevant articles and documents
To be dinuclear or not: Z-DNA induction by nickel complexes
Spingier, Bernhard,Antoni, Philipp M.
, p. 6617 - 6622 (2007)
The left-handed Z-DNA has been identified as a gene regulating element. Therefore the generation of ZDNA through metal complexes might be an innovative way for the regulation of gene expression. Use of the new dinuclear complex N,N,N',N'-tetrakis-[2(3,5-dimethylpyrazol-l-yl)ethylJ-l,3propylenediamine- bis(nickel(II) dinitrate) (2) reversibly induced Z-DNA formation. However, when a 1:1 ratio of metal/dinucleating ligand was used as a control, the midpoint of the B- to Z-DNA transition was at the same nickel concentration as in case of the dinuclear complex. The novel mononuclear analogue, N-methyl-N,N-bis-[2(3,5- dimethylpyrazol-l-yl)ethyl]aminenickel(II)-dinitrate (3) was inducing the Z-DNA at a similar ratio versus nucleotides as free nickel(II) itself. For the first time, proton and nickel binding constants for the bis-[2-(pyrazol-lyl)ethyl] amine ligand system are reported and discussed. Both nickel complexes 2 and 3 were structurally characterized by single crystal analysis. Furthermore, the synthesis of the two new ligands, N,N,N',N,'-tetrakis-[2-(3,5-dimethylpyrazol-l- yl)ethyl]-l,2-propylenediamine (4) and N-methyl-N,N-bis-[2(3,5-dimethylpyrazol- l-yl)ethyl]amine (5) is described. The two major synthetic pathways leading to polypyrazoyl amines in general are critically discussed with respect to yield, reproducibility and handling of the intermediates.
Synthesis, structure, spectra and redox of Cu(II) complexes of chelating bis(benzimidazole) - Thioether ligands as models for electron transfer blue copper proteins
Vaidyanathan,Balamurugan,Sivagnanam,Palaniandavar
, p. 3498 - 3506 (2001)
The tridentate ligand 1,5-bis(benzimidazol-2-yl)-3-thiapentane (L1) with N2S donor set forms the complex [Cu(L1)-(H2O)Cl]Cl 1a and the linear quadridentate ligand 1,8-bis(benzimidazol-2-yl)-3,6-dithiaoctane (L2) with N2S2 donor set forms the complexes [Cu(L2)](ClO4)2·2H2O 2a and [Cu(L2)(NO3)]NO3 2b. The linear pentadentate ligand 1,11-bis(pyrid-2-yl)-3,6,9-trithiaundecane (L3) with N2S3 donor set forms the complex [Cu(L3)](ClO4)2 3. The perchlorate complex [Cu(L4)](ClO4)2·2CH3CN 4 of the pentadentate ligand,N,N-bis(benzimidazol-2-ylmethylthioethyl)methyl-amine (L4) with N3S2 donor set has also been isolated. In 1a Cu(II) is coordinated to the two benzimidazole nitrogens and thioether sulfur of the ligand L1, a chloride ion and a water molecule. The coordination geometry around copper is intermediate between trigonal bipyramidal and square pyramidal geometries and is better described as trigonal bipyramidal distorted square based pyramidal (TBDSBP) with the sulfur and nitrogen atoms and the chloride ion in the equatorial positions and the oxygen of water in the apical position. The coordination geometry around copper(II) in 2b is best described as trigonal bipyramidal, with both the thioether sulfur atoms [Cu-S(1), 2.529(5) and Cu-S(2), 2.438(6) A] and one of the oxygen atoms of the nitrate ion [Cu-O(1), 2.066(13) A] constituting the trigonal plane and both the benzimidazole nitrogens [Cu-N, 1.985(14) and 1.953(13) A] occupying the axial positions. The bulky benzimidazole moieties of the ligand prevent the other nitrate ion from coordinating and favours trigonal bipyramidal geometry in spite of the presence of two six-membered chelate rings. In 4 the coordination plane of Cu(II) is comprised of two benzimidazole nitrogens, one thioether sulfur and N-methyl substituted amine nitrogen atom with the other thioether sulfur atom coordinated axially. The coordination geometry is best described as trigonal bipyramidal distorted square based pyramidal (TBDSBP). The ligand field and EPR spectra of 1a, 2a and 2b are consistent with trigonal bipyramidal geometry in the solid state, whereas two ligand field bands in solution and an axial EPR spectrum in frozen solution were observed suggesting a change in coordination geometry to a square-based one on dissolution. The complexes 3 and 4 exhibit only one ligand field band in the solid state and axial EPR spectrum consistent with a square based geometry. All the complexes exhibit an intense S(σ)→Cu(II) CT band in the range 330-380 nm and a high positive CuII/CuI redox potential.
Mass spectral studies of silyl derivatives of partially hydrolyzed products of nitrogen mustards: Important markers of nitrogen mustard exposure
Chandra, Buddhadeb,Sinha Roy, Kanchan,Shaik, Mahabul,Waghmare, Chandrakant,Palit, Meehir
, (2020/01/21)
Rationale: Nitrogen mustards (NMs) are vesicant class of chemical warfare agents. From the viewpoint of the Chemical Weapons Convention partially hydrolyzed products of nitrogen mustards (pHpNMs) are considered as important markers of nitrogen mustard exposure. The detection of pHpNMs from biological or environmental samples is highly useful for obtaining forensic evidence of exposure to NMs. Methods: Gas chromatography interfaced with tandem mass spectrometry (GC/MS/MS) is a widely used tool for the identification and sensitive detection of metabolites of NMs in complex matrices. The pHpNMs were derivatized using silylating agents as they are highly polar and non-amenable to GC. The mass spectral studies of these silyl derivatives of pHpNMs were performed using GC/MS/MS in both electron ionization (EI) and chemical ionization (CI) mode. Results: Various approaches have been proposed to assess the fragmentation pathways of the trimethylsilyl (TMS) and tert-butyldimethylsilyl (TBDMS) derivatives of pHpNMs. All the proposed fragmentation pathways were based on the product and/or precursor ion scanning of corresponding ions in both EI and CI mode. In the case of EI, most of the fragmentation pathways involved either α-cleavage or inductive cleavage. Conclusions: This is the first report on the MS study of the silyl derivatives of pHpNMs. The study of the two different derivatives of pHpNMs using both EI- and CI-MS provides a reliable, unambiguous identification of pHpNMs in complex environmental and biomedical matrices (such as plasma and urine) during any verification activities.
Rational design of an organocatalyst for peptide bond formation
Handoko,Satishkumar, Sakilam,Panigrahi, Nihar R.,Arora, Paramjit S.
supporting information, p. 15977 - 15985 (2019/10/11)
Amide bonds are ubiquitous in peptides, proteins, pharmaceuticals, and polymers. The formation of amide bonds is a straightforward process: amide bonds can be synthesized with relative ease because of the availability of efficient coupling agents. However, there is a substantive need for methods that do not require excess reagents. A catalyst that condenses amino acids could have an important impact by reducing the significant waste generated during peptide synthesis. We describe the rational design of a biomimetic catalyst that can efficiently couple amino acids featuring standard protecting groups. The catalyst design combines lessons learned from enzymes, peptide biosynthesis, and organocatalysts. Under optimized conditions, 5 mol % catalyst efficiently couples Fmoc amino acids without notable racemization. Importantly, we demonstrate that the catalyst is functional for the synthesis of oligopeptides on solid phase. This result is significant because it illustrates the potential of the catalyst to function on a substrate with a multitude of amide bonds, which may be expected to inhibit a hydrogen-bonding catalyst.
COMPOUNDS AND METHODS for the inhibition of HDAC
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Paragraph 0395-0396, (2015/11/24)
Disclosed are compounds having the formula: wherein X1, X2, X3, R1, R2, R3, R4, Y, A, Z, L and n are as defined herein, and methods of making and using the same.
