Mechlorethamine

Numéro de catalogue: B1211372

Numéro CAS: 51-75-2

Poids moléculaire: 156.05 g/mol

Clé InChI: HAWPXGHAZFHHAD-UHFFFAOYSA-N

Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.

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Vue d'ensemble

1. Description

6. Comparaison avec des composés similaires

2. Méthodes de préparation

7. Propriétés

3. Analyse des réactions chimiques

8. Retrosynthesis analysis

4. Applications de recherche scientifique

9. Avertissement

5. Mécanisme d'action

Description

Il était à l'origine dérivé de la recherche sur le gaz moutarde et est depuis devenu une pierre angulaire dans le traitement de divers cancers, notamment la maladie de Hodgkin, le lymphosarcome et certains types de leucémie . La méchlorethamine est connue pour sa capacité à interférer avec la réplication de l'ADN, conduisant à la mort cellulaire.

Méthodes De Préparation

Voies de synthèse et conditions réactionnelles : La méchlorethamine est synthétisée par réaction de l'éthylèneimine avec l'acide chlorhydrique, suivie de l'addition de la méthylamine. Les conditions réactionnelles impliquent généralement :

Température : Contrôlée autour de 0-5°C pour éviter la décomposition.

Solvant : Souvent réalisée en milieu aqueux.

Purification : Le produit est purifié par distillation ou recristallisation.

Méthodes de production industrielle : Dans les milieux industriels, la méchlorethamine est produite dans des réacteurs à grande échelle avec des contrôles stricts pour garantir la pureté et la sécurité. Le processus implique :

Traitement par lots : Pour maintenir le contrôle des conditions réactionnelles.

Mesures de sécurité : En raison de sa nature toxique, les installations de production sont équipées de systèmes de ventilation et de confinement avancés.

Analyse Des Réactions Chimiques

Types de réactions : La méchlorethamine subit plusieurs types de réactions chimiques, notamment :

Alkylation : Elle forme des liaisons covalentes avec l'ADN, conduisant à des réticulations et des cassures de brins.

Hydrolyse : Dans les milieux aqueux, la méchlorethamine peut s'hydrolyser pour former des composés moins actifs.

Réactifs et conditions courantes :

Réactions d'alkylation : Typiquement réalisées en présence d'ADN ou d'autres nucléophiles.

Hydrolyse : Se produit facilement dans l'eau ou les solutions aqueuses.

Principaux produits formés :

Adduits d'ADN : Les principaux produits des réactions d'alkylation avec l'ADN.

Dérivés hydrolysés : résultant de réactions d'hydrolyse.

4. Applications de la recherche scientifique

La méchlorethamine a une large gamme d'applications dans la recherche scientifique :

Chimie : Utilisée comme composé modèle pour étudier les réactions d'alkylation et les interactions avec l'ADN.

Biologie : Employée dans la recherche sur les mécanismes de réparation de l'ADN et la mutagenèse.

Médecine : Composant clé des schémas de chimiothérapie pour le traitement de divers cancers.

Industrie : Utilisée dans la synthèse d'autres composés pharmaceutiques

5. Mécanisme d'action

La méchlorethamine exerce ses effets par la formation d'ions carbonium, qui alkylent les bases de l'ADN. Cela conduit à la formation de liaisons croisées interbrins et intrabrins, entraînant une mauvaise traduction, des cassures de brins et, finalement, la mort cellulaire. Les principales cibles moléculaires sont les atomes d'azote N7 des bases guanine de l'ADN .

Composés similaires :

Cyclophosphamide : Un autre agent alkylant utilisé en chimiothérapie.

Chlorambucil : Un composé apparenté avec des mécanismes d'action similaires.

Melphalan : Utilisé dans le traitement du myélome multiple et du cancer de l'ovaire.

Comparaison :

Puissance : La méchlorethamine est très puissante et agit rapidement par rapport à certains autres agents alkylants.

Toxicité : Elle présente un profil de toxicité plus élevé, nécessitant une manipulation et une administration prudentes.

Mécanisme : Bien que tous ces composés alkylent l'ADN, l'action rapide et la forte réactivité de la méchlorethamine la rendent unique.

La méchlorethamine reste un composé essentiel dans le domaine de la chimiothérapie, avec des recherches en cours pour explorer tout son potentiel et ses applications.

Applications De Recherche Scientifique

Mechlorethamine has a wide range of applications in scientific research:

Chemistry: Used as a model compound for studying alkylation reactions and DNA interactions.

Biology: Employed in research on DNA repair mechanisms and mutagenesis.

Medicine: A key component in chemotherapy regimens for treating various cancers.

Industry: Utilized in the synthesis of other pharmaceutical compounds

Mécanisme D'action

Mechlorethamine exerts its effects through the formation of carbonium ions, which alkylate DNA bases. This leads to the formation of interstrand and intrastrand cross-links, resulting in miscoding, strand breaks, and ultimately, cell death. The primary molecular targets are the N7 nitrogen atoms of guanine bases in DNA .

Comparaison Avec Des Composés Similaires

Cyclophosphamide: Another alkylating agent used in chemotherapy.

Chlorambucil: A related compound with similar mechanisms of action.

Melphalan: Used in the treatment of multiple myeloma and ovarian cancer.

Comparison:

Potency: Mechlorethamine is highly potent and acts rapidly compared to some other alkylating agents.

Toxicity: It has a higher toxicity profile, necessitating careful handling and administration.

Mechanism: While all these compounds alkylate DNA, this compound’s rapid action and high reactivity make it unique.

This compound remains a critical compound in the field of chemotherapy, with ongoing research exploring its full potential and applications.

Propriétés

IUPAC Name	2-chloro-N-(2-chloroethyl)-N-methylethanamine	Source
Source	PubChem
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Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	HAWPXGHAZFHHAD-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CN(CCCl)CCCl	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C5H11Cl2N	Source
Record name	MECHLORETHAMINE
Source	CAMEO Chemicals
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Related CAS	126-85-2 (N-oxide), 302-70-5 (N-oxide, hydrochloride), 55-86-7 (hydrochloride)	Source
Record name	Mechlorethamine
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DSSTOX Substance ID	DTXSID2020975	Source
Record name	Nitrogen mustard
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Molecular Weight	156.05 g/mol	Source
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Physical Description	Mobile liquid; faint odor of herring. Used as a drug for the treatment of cancer. Formerly used as a gas warfare agent., Colorless to pale yellow, oily liquid with a faint soapy odor or fruity odor at high concentrations; [ATSDR-MMG], Solid	Source
Record name	MECHLORETHAMINE
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Record name	Mechlorethamine
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Boiling Point	189 °F at 18 mmHg (EPA, 1998), 87°C at 1.80E+01 mm Hg, 87 °C @ 18 mm Hg	Source
Record name	MECHLORETHAMINE
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Record name	Mechlorethamine
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Record name	MECHLORETHAMINE
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Solubility	Very soluble, Very slightly soluble in water; miscible with dimethyl formamide, carbon disulfide, carbon tetrachloride, many organic solvents and oils, 3.34e+01 g/L	Source
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Record name	MECHLORETHAMINE
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Record name	Mechlorethamine
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Density	1.118 at 77 °F (EPA, 1998) - Denser than water; will sink, 1.118 @ 25 °C/4 °C	Source
Record name	MECHLORETHAMINE
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Record name	MECHLORETHAMINE
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Vapor Density	5.9 (Air=1)	Source
Record name	MECHLORETHAMINE
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Vapor Pressure	0.42 [mmHg], 0.17 mm Hg @ 25 °C	Source
Record name	Nitrogen mustard (HN-2)
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Record name	MECHLORETHAMINE
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Mechanism of Action	Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations. Mechlorethamine is cell cycle phase-nonspecific., Mechlorethamine, as an alkylating agent, interferes with DNA replication and transcription of RNA, and ultimately results in the disruption of nucleic acid function., The alkylating agent, nitrogen mustard (HN2), is thought to cause apoptosis through production of free oxygen radicals. To explore the mechanism of HN2-induced apoptosis, we utilized ebselen, a selenoorganic compound with potent antioxidant activity. We examined whether ebselen would inhibit apoptosis in BALB/c mouse spleen lymphocytes and human MOLT-4 leukemia cells treated with HN2 (2.5 microM) in vitro. Non-toxic concentrations (<50 microM) of ebselen were found to prevent HN2-induced apoptosis of murine lymphocytes in a dose-dependent manner, as measured by cell viability, hypodiploid DNA formation, and phosphatidylserine externalization. However, ebselen was ineffective at preventing spontaneous apoptosis in these cells, pointing to the selectivity of its action. Furthermore, pretreatment with ebselen at 1-10 microM for 72 hr protected MOLT-4 cells from HN2-induced apoptosis and maintained cell viability and proliferation as monitored by the above-mentioned parameters. This was accompanied by the preservation of mitochondrial transmembrane potential and elevated glutathione levels and by a blockage of caspase-3 and -9 activation. In vivo, ebselen also had a marked protective effect against spleen weight loss associated with lymphocyte apoptosis in mice treated by HN2. Therefore, ebselen provides an efficient protection against HN2-induced cell death in normal and tumoral lymphocytes and might prove useful as an antidote against alkylating agents., Nitrogen mustard (bis(2-chloroethyl) methylamine, HN2) inhibited the binding of upstream factors Sp1 and AP2 to their consensus sequences. At concentrations where 50% of the consensus sequence DNA contained at least one lesion, HN2 inhibited formation of the Sp1 complex by 37% (40 microM HN2) and the AP2 complex by 40% (50 microM HN2). The binding of the TATA binding protein (TBP) to the TATA element was also inhibited by HN2, whereas sulphur mustard and the monofunctional sulphur mustard 2-chloroethyl ethyl sulphide (CEES) resulted in a disproportional extent of inhibition with respect to the level of alkylation. The level of alkylation of the TBP oligonucleotide varied significantly at 100 microM drug, with 80, 42 and 15% of HN2, sulphur mustard and CEES, respectively. However, this level of alkylation inhibited formation of the TBP-DNA complex by 70, 70 and 45%, respectively. This differential sensitivity of transcription factors to mustard-induced DNA damage therefore appears to reside dominantly in the stereochemical differences between the specific mustard lesions., The ability of the antioxidant N-acetylcysteine to prevent apoptosis induced in lymphocytes by nitrogen mustard (HN2) was investigated. HN2 caused a concentration-dependent induction of apoptosis on C3H murine spleen cells, as identified by two criteria: morphological features revealed by microscopical observations and DNA fragmentation visualized by the characteristic "ladder" pattern observed upon agarose gel electrophoresis, as well as by hypodiploid DNA-containing cells revealed by the flow cytometric analysis of propidium iodide labelled cells. The antioxidant N-acetylcysteine (NAC) was found to markedly reduce the occurrence of HN2-induced apoptosis in these cells. This protective effect will still obtained when NAC was added 30 min after HN2. In contrast, the pretreatment of spleen cells with this antioxidant did not provide any significant protection. We also showed that lymphocytes protected by NAC are still able to respond to a mitogenic stimulation. To gain some insight into the mechanisms underlying the cytoprotective action of NAC against HN2, we tested whether or not poly(ADP-ribose) polymerase (PARP, EC 2.4.2.30), a nuclear enzyme that participates in the triggering of apoptosis induced by alkylating agents, is involved. We report that 6(5H)-phenanthridinone, a potent PARP inhibitor, did not affect the ability of NAC to prevent HN2-induced apoptosis under our experimental conditions. Thus, the exact mechanism by which NAC protects lymphocytes from HN2 cytotoxicity has yet to be determined.	Source
Record name	Mechlorethamine
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Record name	MECHLORETHAMINE
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Color/Form	Mobile liquid, Dark liquid, Liquid, colorless/pale yellow when fresh
CAS No.	51-75-2	Source
Record name	MECHLORETHAMINE
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Record name	Mechlorethamine
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Record name	mechlorethamine
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Record name	Nitrogen Mustard-2
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Record name	Ethanamine, 2-chloro-N-(2-chloroethyl)-N-methyl-
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Record name	Nitrogen mustard
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Record name	Chlormethine
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Record name	MECHLORETHAMINE
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Record name	MECHLORETHAMINE
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Record name	Mechlorethamine
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Melting Point	-76 °F (EPA, 1998), -60 °C, 108 - 111 °C	Source
Record name	MECHLORETHAMINE
Source	CAMEO Chemicals
URL	https://cameochemicals.noaa.gov/chemical/5046
Description	CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management.
Explanation	CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.

Record name	Mechlorethamine
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00888
Description	The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information.
Explanation	Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)

Record name	MECHLORETHAMINE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/5083
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Record name	Mechlorethamine
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015025
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Retrosynthesis Analysis

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Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
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Top-N result to add to graph	6

Feasible Synthetic Routes

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