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Chemical Compound Review:

Trimustine 2-chloro-N,N-bis(2- chloroethyl)ethanamine

Synonyms: Triclormetina, Trichlomethine, HN-3, Sinalost base, Trimitan base, ...

Wildenauer, D.B. et al., Gresham, G.L. et al., Sýkora, I. et al., Sýkora, I. et al., Neogi, S. et al., et al.

Gresham, Groenewold, Olson,

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Disease relevance of Hn3 hcl

In one case (the cytostatic TS-160) development of sarcomas was found at the site of subcutaneous administration in the long-term study, and this effect was not observed in the postnatal study [1].
Trichlortriethylamine (TS-160 Spofa) in combination chemotherapy of malignant lymphomas [2].

High impact information on Hn3 hcl

A podand bearing three carboxylic acid groups was synthesized by condensation of tris(2-chloroethyl)amine with 4-hydroxyethylbenzoate followed by hydrolysis of the ester group [3].
The nitrogen blister agents HN-2 (bis(2-chloroethyl)methylamine) and HN-3 (tris(2-chloroethyl)amine) were directly analyzed on the surface of soil samples using ion trap secondary ion mass spectrometry (SIMS) [4].
TS-160 carries a genetic risk for the postmeiotic stages of spermatogenesis (DLM) and is responsible for interference in the morphology of sperm heads through its action on spermatocytes [5].
The cytostatic TS-160 (trichloromethine hydrochloride, tris-/2-chloroethyl/amine hydrochloride) was injected subcutaneously into SPF Wistar rats of both sexes [6].
The influence of tris(2-chloroethyl)amine on shape changes of human erythrocytes and ghosts was studied in vitro and correlated with alterations in the molecular structure of the membrane [7].

Biological context of Hn3 hcl

It is suggested that the observed conservation of cell shape is preferentially caused by the reaction of tris(2-chloroethyl)amine with spectrin [7].

Anatomical context of Hn3 hcl

(3) The amount of chlorpromazine necessary for transformation of erythrocytes into stomatocytes was increased for tris(2-chloroethyl)amine-pretreated cells and was dependent on the degree of reaction with tris(2-chloroethyl)amine [7].

Associations of Hn3 hcl with other chemical compounds

(1) Reaction with 1--2 mM tris(2-chloroethyl)amine, a concentration which caused polymerisation of spectrin as detected by sodium dodecyl sulphate polyacrylamide gel electrophoresis, protected intact erythrocytes against metabolically induced shape changes [7].
Different inhibitory effect of nitrogen mustard (HN2) and TS-160 (HN3) on choline transport in L 5178Y lymphoblasts [8].

Analytical, diagnostic and therapeutic context of Hn3 hcl

Sodium dodecyl sulphate polyacrylamide gel electrophoresis and autoradiography of the membrane proteins from 32-P-treated cells showed that the spectrin component 2 and the polymerisation products generated by the reaction with tris(2-chloroethyl)amine were labelled [7].

References

Comparability of results of postnatal and long-term tests for carcinogenicity. Sýkora, I., Vortel, V. Neoplasma (1993) [Pubmed]
Trichlortriethylamine (TS-160 Spofa) in combination chemotherapy of malignant lymphomas. Klener, P., Donner, L. Neoplasma (1975) [Pubmed]
An infinite water chain passes through an array of Zn(II) metallocycles built with a podand bearing terminal carboxylates. Neogi, S., Bharadwaj, P.K. Inorganic chemistry. (2005) [Pubmed]
Identification of the nitrogen-based blister agents bis(2-chloroethyl)methylamine (HN-2) and tris(2-chloroethyl)amine (HN-3) and their hydrolysis products on soil using ion trap secondary ion mass spectrometry. Gresham, G.L., Groenewold, G.S., Olson, J.E. Journal of mass spectrometry : JMS. (2000) [Pubmed]
Trichlormethine hydrochloride and correlation of its mutagenic and toxic effects on male germ cells in mice. Sýkora, I., Gandalovicová, D. Mutat. Res. (1992) [Pubmed]
Carcinogenicity of trichloromethine hydrochloride (TS-160 Spofa) and morphological damage after its intraamniotic injection. Sýkora, I., Vortel, V., Marhan, O., Dynterová, A. Neoplasma (1981) [Pubmed]
Reactions of the alkylating agent tris(2-chloroethyl)-amine with the erythrocyte membrane. Effects on shape changes of human erythrocytes and ghosts. Wildenauer, D.B., Reuther, H., Remien, J. Biochim. Biophys. Acta (1980) [Pubmed]
Different inhibitory effect of nitrogen mustard (HN2) and TS-160 (HN3) on choline transport in L 5178Y lymphoblasts. Ujházy, V., Kolarov, J., Kuzela, S., Krempaský, V., Bohunická, E. Neoplasma (1975) [Pubmed]

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