Mechlorethamine hydrochloride Chemical Properties

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

pka

pKa 6.43 (Uncertain)

form 

Solid

color 

Leaflets from Me2CO or CHCl3

Sensitive 

Hygroscopic

Merck 

13,5798

Stability:

Stable. Hygroscopic.

CAS DataBase Reference

55-86-7(CAS DataBase Reference)

EPA Substance Registry System

Nitrogen mustard (HN-2), hydrochloride (55-86-7)

Safety Information

Hazard Codes 

T+

Risk Statements 

45-46-28-34-42/43-27/28-61

Safety Statements 

53-36/37/39-45

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)

MSDS

• Language:English Provider:2-Chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride
• Language:English Provider:SigmaAldrich

Mechlorethamine hydrochloride Usage And Synthesis

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

White Solid

Chemical Properties

Highly toxic white to yellowish crystalline solid or powder. May be available as an unstable aqueous solution. Fish-like odor.

Uses

xanthine oxidase/dehydrogenase inhibitor

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

It has been used as an antineoplastic. A nitrogen mustard prepared by action of thionyl chloride on 2,2’(methylimino)- diethanol in trichloroethylene.

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.

General Description

White to off-white crystals or powder with a fishy odor. Initial pH (2% aqueous solution) 3.0-4.0.

General Description

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.

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