| Identification | More | [Name]
Chlormethine hydrochloride | [CAS]
55-86-7 | [Synonyms]
2,2'-DICHLORO-N-METHYLDIETHYLAMINE HYDROCHLORIDE
AURORA KA-7722
BIS(2-CHLOROETHYL)METHYLAMINE HYDROCHLORIDE
CHLORMETHINE HYDROCHLORIDE
CLORMETHINE HCL
MECHLORETHAMINE
MECHLORETHAMINE HYDROCHLORIDE
MUSTINE HYDROCHLORIDE
NITROGEN MUSTARD
NITROGEN MUSTARD HYDROCHLORIDE
N-METHYLBIS(2-CHLOROETHYL)AMINE HYDROCHLORIDE
N-METHYL-DI(2-CHLORO)-ETHYLAMINE
1,5-dichloro-3-methyl-3-azapentanehydrochloride
2-chloro-n-(2-chloroethyl)-n-methylethanaminehydrochlroide
2-chloro-n-(2-chloroethyl)-n-methyl-ethanaminhydrochloride
antimit
azotoyperite
beta,beta’-dichlorodiethyl-n-methylaminehydrochloride
c6866
caryolysine | [EINECS(EC#)]
200-246-0 | [Molecular Formula]
C5H12Cl3N | [MDL Number]
MFCD00012517 | [Molecular Weight]
192.51 | [MOL File]
55-86-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Highly toxic white to yellowish crystalline
solid or powder. May be available as an unstable aqueous
solution. Fish-like odor. | [Melting point ]
108-111 °C(lit.)
| [Boiling point ]
315.95°C (rough estimate) | [density ]
1.4424 (rough estimate) | [refractive index ]
1.6300 (estimate) | [storage temp. ]
−20°C | [solubility ]
H2O: very soluble | [form ]
Solid | [pka]
pKa 6.43 (Uncertain) | [color ]
Leaflets from Me2CO or CHCl3 | [Stability:]
Stable. Hygroscopic. | [Sensitive ]
Hygroscopic | [Merck ]
13,5798 | [CAS DataBase Reference]
55-86-7(CAS DataBase Reference) | [EPA Substance Registry System]
55-86-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
R45:May cause cancer.
R28:Very Toxic if swallowed.
R34:Causes burns.
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
IA2100000
| [TSCA ]
Yes | [HazardClass ]
6.1(a) | [PackingGroup ]
II | [HS Code ]
2921196190 | [Hazardous Substances Data]
55-86-7(Hazardous Substances Data) | [Toxicity]
LD50 in rats (mg/kg): 1.1 i.v.; 1.9 s.c. (Anslow) |
| Hazard Information | Back Directory | [General Description]
White to off-white crystals or powder with a fishy odor. Initial pH (2% aqueous solution) 3.0-4.0. | [Reactivity Profile]
Dry crystals are stable at temperatures up to 104° F. This chemical is incompatible with strong oxidizing agents. . | [Air & Water Reactions]
Hygroscopic. Water soluble. | [Hazard]
Highly toxic, vesicant, and strongly irritant
to mucous membranes. | [Fire Hazard]
Flash point data for this chemical are not available. NITROGEN MUSTARD HYDROCHLORIDE is probably combustible. | [First aid]
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a one-way
valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate
contaminated clothing and shoes. In case of contact with
substance, immediately flush skin or eyes with running water
for at least 20 minutes. For minor skin contact, avoid spreading
material on unaffected skin. Keep victim warm and
quiet. Effects of exposure (inhalation, ingestion or skin contact)
to substance may be delayed. Ensure that medical personnel
are aware of the material(s) involved and take
precautions to protect themselves. Medical observation is
recommended for 24 48 hours after breathing overexposure,
as pulmonary edema may be delayed. As first aid for pulmonary
edema, a doctor or authorized paramedic may consider
administering a drug or other inhalation therapy. | [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. | [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]
Highly toxic white to yellowish crystalline
solid or powder. May be available as an unstable aqueous
solution. Fish-like odor. | [Chemical Properties]
White Solid | [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. | [Uses]
It has been used as an antineoplastic. A nitrogen mustard prepared by action of thionyl chloride on 2,2’(methylimino)-
diethanol in trichloroethylene. | [Uses]
Mechlorethamine hydrochloride USP (Mustargen)is used to treat Hodgkin’s disease; non-Hodgkin’s lymphomas; lymphosarcoma; cancer of breast, ovary, lung; neoplastic effusion. | [Uses]
xanthine oxidase/dehydrogenase inhibitor | [Definition]
ChEBI: The hydrochloride salt of mechlorethamine. | [Indications]
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. | [Indications]
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. | [Brand name]
Mustargen (Ovation). | [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. | [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. |
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