Mechlorethamine

Número de catálogo: B1211372

Número CAS: 51-75-2

Peso molecular: 156.05 g/mol

Clave InChI: HAWPXGHAZFHHAD-UHFFFAOYSA-N

Atención: Solo para uso de investigación. No para uso humano o veterinario.

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Descripción general

1. Descripción

6. Comparación con compuestos similares

2. Métodos de preparación

7. Propiedades

3. Análisis de reacciones químicas

8. Retrosynthesis analysis

4. Aplicaciones científicas de investigación

9. Descargo de responsabilidad

5. Mecanismo de acción

Descripción

Originalmente se derivó de la investigación del gas mostaza y desde entonces se ha convertido en una piedra angular en el tratamiento de varios cánceres, incluida la enfermedad de Hodgkin, el linfosarcoma y ciertos tipos de leucemia . La mostaza de nitrógeno es conocida por su capacidad para interferir con la replicación del ADN, lo que lleva a la muerte celular.

Métodos De Preparación

Rutas sintéticas y condiciones de reacción: La mostaza de nitrógeno se sintetiza mediante la reacción de etilenimina con ácido clorhídrico, seguida de la adición de metilamina. Las condiciones de reacción generalmente implican:

Temperatura: Controlada a alrededor de 0-5 °C para evitar la descomposición.

Solvente: A menudo se lleva a cabo en un medio acuoso.

Purificación: El producto se purifica mediante destilación o recristalización.

Métodos de producción industrial: En entornos industriales, la mostaza de nitrógeno se produce en reactores a gran escala con controles estrictos para garantizar la pureza y la seguridad. El proceso involucra:

Procesamiento por lotes: Para mantener el control sobre las condiciones de reacción.

Medidas de seguridad: Debido a su naturaleza tóxica, las instalaciones de producción están equipadas con sistemas avanzados de ventilación y contención.

Análisis De Reacciones Químicas

Tipos de reacciones: La mostaza de nitrógeno experimenta varios tipos de reacciones químicas, que incluyen:

Alquilación: Forma enlaces covalentes con el ADN, lo que lleva a la reticulación y la ruptura de las cadenas.

Hidrólisis: En entornos acuosos, la mostaza de nitrógeno puede hidrolizarse para formar compuestos menos activos.

Reactivos y condiciones comunes:

Reacciones de alquilación: Generalmente se llevan a cabo en presencia de ADN u otros nucleófilos.

Hidrólisis: Ocurre fácilmente en agua o soluciones acuosas.

Principales productos formados:

Aductos de ADN: Los principales productos de las reacciones de alquilación con el ADN.

Derivados hidrolizados: Resultante de reacciones de hidrólisis.

Aplicaciones Científicas De Investigación

La mostaza de nitrógeno tiene una amplia gama de aplicaciones en la investigación científica:

Química: Se utiliza como un compuesto modelo para estudiar reacciones de alquilación e interacciones con el ADN.

Biología: Se emplea en la investigación sobre mecanismos de reparación del ADN y mutagénesis.

Medicina: Un componente clave en los regímenes de quimioterapia para el tratamiento de varios cánceres.

Industria: Se utiliza en la síntesis de otros compuestos farmacéuticos

Mecanismo De Acción

La mostaza de nitrógeno ejerce sus efectos a través de la formación de iones carbonio, que alquilatan las bases del ADN. Esto lleva a la formación de enlaces cruzados intercatenarios e intracatenarios, lo que resulta en una codificación errónea, rotura de las cadenas y, en última instancia, la muerte celular. Los principales objetivos moleculares son los átomos de nitrógeno N7 de las bases guanina en el ADN .

Compuestos similares:

Ciclofosfamida: Otro agente alquilante utilizado en la quimioterapia.

Clorambucil: Un compuesto relacionado con mecanismos de acción similares.

Melfalán: Se utiliza en el tratamiento del mieloma múltiple y el cáncer de ovario.

Comparación:

Potencia: La mostaza de nitrógeno es altamente potente y actúa rápidamente en comparación con algunos otros agentes alquilantes.

Toxicidad: Tiene un perfil de toxicidad más alto, lo que requiere un manejo y una administración cuidadosos.

Mecanismo: Si bien todos estos compuestos alquilatan el ADN, la acción rápida y la alta reactividad de la mostaza de nitrógeno la hacen única.

La mostaza de nitrógeno sigue siendo un compuesto fundamental en el campo de la quimioterapia, con investigaciones en curso que exploran su potencial y aplicaciones completos.

Comparación Con Compuestos Similares

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.

Propiedades

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
Source	PubChem
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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
Record name	Mechlorethamine
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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	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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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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Feasible Synthetic Routes

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