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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:22 UTC

HMDB ID

HMDB0015025

Secondary Accession Numbers

HMDB15025

Metabolite Identification

Common Name

Mechlorethamine

Description

Mechlorethamine is only found in individuals that have used or taken this drug. It is a vesicant and necrotizing irritant destructive to mucous membranes. It was formerly used as a war gas. The hydrochloride is used as an antineoplastic in Hodgkin's disease and lymphomas. It causes severe gastrointestinal and bone marrow damage. [PubChem]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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,2'-Dichloro-N-methyldiethylamine	ChEBI
beta,Beta'-dichlorodiethyl-N-methylamine	ChEBI
Bis(2-chloroethyl)methylamine	ChEBI
Bis(beta-chloroethyl)methylamine	ChEBI
Chlormethine	ChEBI
Methylbis(2-chloroethyl)amine	ChEBI
Methylbis(beta-chloroethyl)amine	ChEBI
N-Methyl-bis(2-chloroethyl)amine	ChEBI
N-Methyl-bis(beta-chloroethyl)amine	ChEBI
Nitrogen mustard	ChEBI
b,Beta'-dichlorodiethyl-N-methylamine	Generator
Β,beta'-dichlorodiethyl-N-methylamine	Generator
Bis(b-chloroethyl)methylamine	Generator
Bis(β-chloroethyl)methylamine	Generator
Methylbis(b-chloroethyl)amine	Generator
Methylbis(β-chloroethyl)amine	Generator
N-Methyl-bis(b-chloroethyl)amine	Generator
N-Methyl-bis(β-chloroethyl)amine	Generator
Chlorethazine	HMDB
HN2	HMDB
MBA	HMDB
Mechloroethamine	HMDB
Mecloretamina	HMDB
Mustine	HMDB
Mechlorethamine hydrochloride N oxide	HMDB
Mechlorethamine hydrochloride N-oxide	HMDB
Merck frosst brand OF mechlorethamine hydrochloride	HMDB
NSC-762	HMDB
Embichin	HMDB
Hydrochloride N-oxide, mechlorethamine	HMDB
Mechlorethamine N oxide	HMDB
Mechlorethamine oxide	HMDB
Merck brand OF mechlorethamine hydrochloride	HMDB
Mitomen	HMDB
Nitrogen mustard N oxide	HMDB
Caryolysine	HMDB
Cloramin	HMDB
Hydrochloride, mechlorethamine	HMDB
Methylchlorethamine	HMDB
N-Oxide, mechlorethamine hydrochloride	HMDB
N-Oxide, nitrogen mustard	HMDB
Nitrogen mustard N-oxide	HMDB
Nitrogranulogen	HMDB
Nitromin	HMDB
Mechlorethamine hydrochloride	HMDB
Mechlorethamine N-oxide	HMDB
Mustargen	HMDB
NSC 762	HMDB

Chemical Formula

C₅H₁₁Cl₂N

Average Molecular Weight

156.054

Monoisotopic Molecular Weight

155.026854771

IUPAC Name

bis(2-chloroethyl)(methyl)amine

Traditional Name

mechlorethamine

CAS Registry Number

51-75-2

SMILES

CN(CCCl)CCCl

InChI Identifier

InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3

InChI Key

HAWPXGHAZFHHAD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen mustard compounds

Alternative Parents

Substituents

Nitrogen mustard
Tertiary aliphatic amine
Tertiary amine
Organopnictogen compound
Hydrocarbon derivative
Organochloride
Organohalogen compound
Amine
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organochlorine compound (CHEBI:28925 )
nitrogen mustard (CHEBI:28925 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0015025)
Extracellular (HMDB: HMDB0015025)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Not Available

Role

Biological role

Alkylating agent (HMDB: HMDB0015025)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	108 - 111 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	33.4 g/L	Not Available
LogP	1.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	33.4 g/L	ALOGPS
logP	1.31	ALOGPS
logP	1.52	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Basic)	6.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	38.67 m³·mol⁻¹	ChemAxon
Polarizability	15.84 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	132.671	30932474
DeepCCS	[M-H]-	129.752	30932474
DeepCCS	[M-2H]-	166.278	30932474
DeepCCS	[M+Na]+	141.393	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	136.8	32859911
AllCCS	[M-H]-	136.1	32859911
AllCCS	[M+Na-2H]-	139.6	32859911
AllCCS	[M+HCOO]-	143.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mechlorethamine	CN(CCCl)CCCl	1556.1	Standard polar	33892256
Mechlorethamine	CN(CCCl)CCCl	1045.2	Standard non polar	33892256
Mechlorethamine	CN(CCCl)CCCl	1088.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mechlorethamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9400000000-37f4081d8c3fd8e974c6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mechlorethamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-7900000000-66a0ef3007bd03bd9367	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 10V, Positive-QTOF	splash10-0a4i-0900000000-2282bef263bfa8a41123	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 20V, Positive-QTOF	splash10-0a4i-7900000000-b0b770790e86670fc2a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 40V, Positive-QTOF	splash10-03di-9000000000-5d96975a96ed8783c02e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 10V, Negative-QTOF	splash10-0udi-1900000000-7801c92cb7dc490c200d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 20V, Negative-QTOF	splash10-0uxr-4900000000-0df7677828ba3d2293ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 40V, Negative-QTOF	splash10-08i3-9100000000-67d0e475a21ed8a44dca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 10V, Positive-QTOF	splash10-0a4i-0900000000-b39c5053cfb605f67e08	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 20V, Positive-QTOF	splash10-08fr-9400000000-9836caddbb3ebb21e8bb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 40V, Positive-QTOF	splash10-03di-9000000000-dcc5bf7c33b77979d5a5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 10V, Negative-QTOF	splash10-0ue9-8900000000-60357d33a598f0fa346f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 20V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mechlorethamine 40V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00888	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00888	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00888

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3893

KEGG Compound ID

C07115

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mechlorethamine

METLIN ID

Not Available

PubChem Compound

4033

PDB ID

Not Available

ChEBI ID

28925

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Mechlorethamine (HMDB0015025)

MOL for HMDB0015025 (Mechlorethamine)

3D MOL for HMDB0015025 (Mechlorethamine)

3D SDF for HMDB0015025 (Mechlorethamine)

3D-SDF for HMDB0015025 (Mechlorethamine)

PDB for HMDB0015025 (Mechlorethamine)

3D PDB for HMDB0015025 (Mechlorethamine)

SMILES for HMDB0015025 (Mechlorethamine)

INCHI for HMDB0015025 (Mechlorethamine)

Structure for HMDB0015025 (Mechlorethamine)

3D Structure for HMDB0015025 (Mechlorethamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra