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Details

Stereochemistry ACHIRAL
Molecular Formula C6H12Cl3N.ClH
Molecular Weight 240.986
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICHLORMETHINE HYDROCHLORIDE

SMILES

Cl.ClCCN(CCCl)CCCl

InChI

InChIKey=VEAUDLLZYJVHRI-UHFFFAOYSA-N
InChI=1S/C6H12Cl3N.ClH/c7-1-4-10(5-2-8)6-3-9;/h1-6H2;1H

HIDE SMILES / InChI

Molecular Formula C6H12Cl3N
Molecular Weight 204.525
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://monographs.iarc.fr/ENG/Monographs/vol50/mono50-11.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2615874 | https://www.ncbi.nlm.nih.gov/pubmed/6188044

Trichlormethine is a nitrogen mustard vesicant that has application in chemical warfare and has been used as a cytostatic alkylating agent in leukemia and lymphoma therapy. Trichlormethine was tested for carcinogenicity by subcutaneous injection in mice and rats. The study in mice was inadequate for evaluation. In rats, trichlormethine induced a high incidence of sarcomas (mostly spindle-cell type) in animals of each sex at the site of subcutaneous injection, as well as a few intestinal adenocarcinomas; neither tumor type was seen in controls. Trichlormethine caused vomiting, anorexia and blood-containing feces in dogs a few hours after a single intravenous injection of 1 mg/kg BW. Decreased peripheral lymphocyte counts were observed in rabbits injected intravenously and in mice injected subcutaneously with trichlormethine. Trichlormethine was tested for carcinogenicity by subcutaneous injection in mice and rats. ln rats, trichlormethine induced a high incidence of sarcomas (mostly spindle-cell type) in animals of each sex at the site of subcutaneous injection, as well as a few intestinal adenocarcinomas; neither tumor type was seen in controls. Trichlormethine is possibly carcinogenic to humans (Group 2B).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Quantitation of biomarkers of exposure to nitrogen mustards in urine from rats dosed with nitrogen mustards and from an unexposed human population.
2004 Jul-Aug
An infinite water chain passes through an array of Zn(II) metallocycles built with a podand bearing terminal carboxylates.
2005 Feb 21
Trichloromethyl ketones as synthetically versatile donors: application in direct catalytic mannich-type reactions and the stereoselective synthesis of azetidines.
2006 May 5
Development of a liquid chromatography-multiple reaction monitoring procedure for concurrent verification of exposure to different forms of mustard agents.
2008 Jan-Feb
Sulfur mustard research--strategies for the development of improved medical therapy.
2008 Jun 10
Poly[[{μ(3)-tris-[2-(4-phenyl-1,2,3-triazol-1-yl)eth-yl]amine}silver(I)] hexa-fluorido-phosphate].
2008 Sep 13
Amplitude-modulated electromagnetic fields for the treatment of cancer: discovery of tumor-specific frequencies and assessment of a novel therapeutic approach.
2009 Apr 14
Development history and concept of an oral anticancer agent S-1 (TS-1): its clinical usefulness and future vistas.
2009 Jan
[Study on the influence factors of human peripheral blood B lymphocyte transformation by Epstein-Barr virus].
2009 Sep
Chemotherapy for early-stage breast cancer: a brief history.
2009 Sep
The role of funding and policies on innovation in cancer drug development.
2010
Biology-driven cancer drug development: back to the future.
2010 Apr 12
Ameliorative effect of DRDE 07 and its analogues on the systemic toxicity of sulphur mustard and nitrogen mustard in rabbit.
2010 Sep
Patents

Patents

Sample Use Guides

A group of 20 mice (age, strain and sex unspeified) received weekly subcutaneous injections of trichlormethine (purity unspeified) at 1mg/kg bw in aqueous solution for ten weeks, afer which time only four mice were alive and treatment was terminated.
Route of Administration: Other
In Vitro Use Guide
About 2 x 10^6 exponentially growing V79 cells (3.5 x l0^4 cells/cm 2) were treated with 0-10 mkg TS160/ml. (TSl60 was diluted in complete medium, in a medium without serum or in PBS buffer.) Then the cells were washed, resuspended by means of 0.025% trypsin in 0.02% EDTA and tested for their growth activity, plating efficiency, the course of macromolecular syntheses and for the presence of 6-thioguanine-resistant (6-TGr) mutants. The treated cells were plated on a series of Petri dishes, diameter 5 cm (4 x 10^4 cells per dish) and incubated at 37°C. At 24-h intervals, the cells were removed from individual Petri dishes and the numbers of cells/dish were counted. The cytostatic agent TSt60 inhibited DNA synthesis in V79 cells while the course of RNA synthesis and protein synthesis were not changed significantly.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:47:56 GMT 2023
Edited
by admin
on Fri Dec 15 18:47:56 GMT 2023
Record UNII
00238AP6R9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRICHLORMETHINE HYDROCHLORIDE
MI   WHO-DD  
Common Name English
NSC-30211
Code English
TRICHLORMETHINE HCL
Common Name English
TRICHLORMETHINE HYDROCHLORIDE [MI]
Common Name English
NSC-759837
Code English
TRIMUSTINE HYDROCHLORIDE
Common Name English
Trichlormethine hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
MERCK INDEX
m11060
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6074835
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY
FDA UNII
00238AP6R9
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY
SMS_ID
100000084661
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY
NSC
759837
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY
NSC
30211
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY
PUBCHEM
61220
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY
CAS
817-09-4
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY
EVMPD
SUB04943MIG
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-442-3
Created by admin on Fri Dec 15 18:47:56 GMT 2023 , Edited by admin on Fri Dec 15 18:47:56 GMT 2023
PRIMARY
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