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Chemical Compound Review

CHLOROFORM     trichloromethane

Synonyms: Chloroforme, Cloroformio, Trichloroform, Trichlormethan, Triclorometano, ...
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Disease relevance of chloroform

  • The added organism was Pseudomonas stutzeri KC (strain KC), a denitrifying bacterium that cometabolically degrades CT without producing chloroform (CF) [1].
  • The CHCl3 treatment significantly reduced the efficacy of the vaccine to protect vaccinates against Marek's disease challenge [2].
  • Further studies need to be conducted to elucidate the mechanisms mediating the interactive toxicity of BrCCl3 and CHCl3 [3].
  • The Antimicrobial Effect of Chloroform on Enterococcus faecalis After Gutta-Percha Removal [4].
  • It was also observed that chloroform concentration increased with the elapsed time up to one and six days to water samples spiked with humic substances and algae blue green, respectively and decreased along 30 days [5].

High impact information on chloroform

  • Labelled reaction products were separated from substrate using chloroform: methanol extraction.Key results:In cytosolic fractions from rat brain, URB602 and URB754 inhibited the hydrolysis of 2-oleoylglycerol with IC(50) values of 25 and 48 muM, respectively [6].
  • The major urinary sesamin metabolite in the chloroform extract was collected using HPLC diode array detector and characterized as (1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo-[3,3,0]octane using NMR and mass spectroscopy [7].
  • Interestingly, CF did not affect the growth of PCE-nondechlorinating SD (small deletion) and LD (large deletion) variants, where the former fails to transcribe the pceABC genes caused by a deletion of the promoter and the latter lost the entire pceABCT gene cluster [8].
  • Quadruply-hydrogen-bonded porphyrin homodimer Zn1.Zn1 has been designed, assembled, and evaluated as a supramolecular cleft-featured receptor for its ability to bind dipyridyl guests in chloroform-d. Monomer Zn1 consists of a 2-ureidopyrimidin-4(1H)-one unit, which was initially reported by Meijer et al., and a zinc porphyrin unit [9].
  • In addition, beta-lactamase released by osmotic shock treatment was found to be unstable during storage at -20 degrees C or during the 18 h period of iso-electric focusing at +4 degrees C. Chloroform treatment produced similar band patterns and at least as good an enzyme yield as ultrasonic disintegration and was equally simple and fast to perform [10].

Chemical compound and disease context of chloroform


Biological context of chloroform

  • This reveals that Waters, during his visit to England in 1936, inspired British anesthetists to discover more of Snow's early contributions to anesthesiology, even though Waters himself did not possess On Chloroform and Other Anaesthetics [15].
  • Degradation kinetics of CT and chloroform (CF) were generally very rapid with reaction rates comparable to rates that can be obtained with zero-valent iron [16].
  • Chloroform was the major species of THMs, especially in the water plant of south Taiwan. Chloroform contributed the majority of the lifetime cancer risks (range: 87.5-92.5%) of total risks from the three water supply areas [17].
  • Three of the four THMs also significantly reduced glomerular filtration rate (GFR), with only CHCl3 failing to demonstrate an effect at 3 mmol/kg [18].
  • No effects were observed with 7.5 mg/kg of HE, CF, CAF or AF, except for an increase in defecation induced by AF [19].

Anatomical context of chloroform

  • It was discovered that the cell-free exudates of the methanogen Methanosarcina thermophila were capable of carbon tetrachloride (CT) and chloroform (CF) degradation [20].
  • Finally, with microsomes, the inactivation was larger with CCl4 (CO binding, 58%; haem assay, 50%; porphyrin fluorescence, 33%) than with CCl3Br (CO binding, 33%; haem assay, 10%) or CHCl3 (haem assay, 9%; CO binding, 6%) [21].
  • RESULTS: Chloroform treatment did not significantly affect GST activities in erythrocytes of control subjects while the activities of erythrocyte total GST and alpha-GST were significantly increased in all anemic patients (P<0.001) [22].
  • The CHCl3 exhibited the potent proliferation of osteoblasts [23].
  • Weakly polar chloroform-d has a significant influence on the organization of water in a spongy component of bone tissue [24].

Associations of chloroform with other chemical compounds

  • Proton magnetic resonance spectra of 17 xi-hydroxy-17 xi-methyl-5 xi-androstane C-3 ketone and C-3 xi alcohol isomers in chloroform-d and pyridine-d5 [25].
  • Carbon-13 NMR spectroscopy at 100.6 MHz revealed that these molecules existed in deuterochloroform solution as unequal mixtures of cis (syn)- and trans (anti)-rotational isomers [26].
  • A chloroform extract of the roots of the Egyptian SALVIA LANIGERA Poir. afforded two new orthoquinones, lanigerone (8-hydroxy-3-isopropyl-7-methyl-1,2-naphthoquinone) and salvigerone (methyl 1,10-seco-5(10),6,8,13-abietatetraene-11,12-dion-1-oate) together with two known diterpenoids, arucadiol and pisiferal [27].
  • This procedure was used to reliably transfer gold nanoparticles with diameters between 45 and 100 nm from aqueous solution to organic solvents such as dimethyl sulfoxide and chloroform [28].
  • In addition to known compounds, sigmoidin C and 8-(3,3-dimethylallyl)-erythrinin C, also called senegalensin, a new isoflavone glycoside designated auriculatin 4'- O-glucoside was isolated from the chloroform extract of the stem bark of ERYTHRINA ERIOTRICHA [29].

Gene context of chloroform

  • Large solvent shifts for the 13C resonance in TMS in either deuterochloroform or methanol are observed, being +0.71 ppm and -0.74 ppm from external TMS, respectively [30].
  • A correlation between potential for free radical formation (CCl3Br > CCl4 > CHCl3 > CH2Cl2) and extent of haem inactivation was observed with all methods for Hb, but not for microsomal P-450 or MHA [21].
  • CFB pretreatment also diminished elevation in plasma SDH activity produced by CHCl3 in CD-1 mice, while BUN was significantly elevated in both groups, indicating that CFB did not protect against CHCl3-induced nephrotoxicity [31].
  • Caragana microphylla Lam. seeds showed analgesic activity, with the chloroform fraction showing the strongest analgesic activity among the fractions [32].
  • METHODS: Chloroform extract, benzene chromatographic fraction of the chloroform extract, its methanol and ethyl acetate sub-fractions and the isolated compounds from the sub-fractions i.e., ECP 1 & 2 and MCP 1 &2, of the seeds of Carica papaya were used at concentrations of 0.1%, 0.5%, 1% and 2% [33].

Analytical, diagnostic and therapeutic context of chloroform


  1. Development, operation, and long-term performance of a full-scale biocurtain utilizing bioaugmentation. Dybas, M.J., Hyndman, D.W., Heine, R., Tiedje, J., Linning, K., Wiggert, D., Voice, T., Zhao, X., Dybas, L., Criddle, C.S. Environ. Sci. Technol. (2002) [Pubmed]
  2. Vaccination against Marek's disease and infectious bursal disease. II. Titration and in vivo efficacy of the coinfection-derived bivalent live vaccine for turkey herpesvirus and infectious bursal disease virus. Chang, J.D., Eidson, C.S., Kleven, S.H., Fletcher, O.J. Poult. Sci. (1984) [Pubmed]
  3. The interactive toxicity of CHCl3 and BrCCl3 in precision-cut rat liver slices. Azri-Meehan, S., Mata, H.P., Gandolfi, A.J., Brendel, K. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1994) [Pubmed]
  4. The Antimicrobial Effect of Chloroform on Enterococcus faecalis After Gutta-Percha Removal. Edgar, S.W., Gordon Marshall, J., Craig Baumgartner, J. Journal of endodontics (2006) [Pubmed]
  5. Monitoring the trihalomethanes present in water after treatment with chlorine under laboratory condition. Paim, A.P., Souza, J.B., Adorno, M.A., Moraes, E.M. Environmental monitoring and assessment (2007) [Pubmed]
  6. Lack of selectivity of URB602 for 2-oleoylglycerol compared to anandamide hydrolysis in vitro. Vandevoorde, S., Jonsson, K.O., Labar, G., Persson, E., Lambert, D.M., Fowler, C.J. Br. J. Pharmacol. (2007) [Pubmed]
  7. Quantitative NMR analysis of a sesamin catechol metabolite in human urine. Moazzami, A.A., Andersson, R.E., Kamal-Eldin, A. J. Nutr. (2007) [Pubmed]
  8. Effects of Chloromethanes on Growth of and Deletion of the pce Gene Cluster in Dehalorespiring Desulfitobacterium hafniense Strain Y51. Futagami, T., Yamaguchi, T., Nakayama, S., Goto, M., Furukawa, K. Appl. Environ. Microbiol. (2006) [Pubmed]
  9. Recognition through self-assembly. A quadruply-hydrogen-bonded, strapped porphyrin cleft that binds dipyridyl molecules and a [2]rotaxane. Shao, X.B., Jiang, X.K., Zhao, X., Zhao, C.X., Chen, Y., Li, Z.T. J. Org. Chem. (2004) [Pubmed]
  10. Evaluation of five different methods to prepare bacterial extracts for the identification of beta-lactamases by isoelectric focusing. Arstila, T., Jacoby, G.A., Huovinen, P. J. Antimicrob. Chemother. (1993) [Pubmed]
  11. Antimicrobial activity of volatile components and various extracts of the red alga Jania rubens. Karabay-Yavasoglu, N.U., Sukatar, A., Ozdemir, G., Horzum, Z. Phytotherapy research : PTR (2007) [Pubmed]
  12. In vitro cytotoxic and non-genotoxic effects of gutta-percha solvents on mouse lymphoma cells by single cell gel (comet) assay. Ribeiro, D.A., Marques, M.E., Salvador, D.M. Brazilian dental journal (2006) [Pubmed]
  13. Ketone potentiation of haloalkane-induced hepato- and nephrotoxicity. I. Dose-response relationships. Raymond, P., Plaa, G.L. Journal of toxicology and environmental health. (1995) [Pubmed]
  14. RT-PCR and cell culture infectivity assay to detect enteroviruses during drinking water treatment processes. Ali, M.A., El-Esnawy, N.A., Shoaeb, A.R., Ibraheim, M., El-Hawaary, S.E. The Journal of the Egyptian Public Health Association (1999) [Pubmed]
  15. The Wood Library-Museum's 1858 edition of John Snow's On chloroform and other anaesthetics. Maltby, J.R., Bamforth, B.J. Anesth. Analg. (1990) [Pubmed]
  16. Reductive dechlorination of chlorinated methanes in cement slurries containing Fe(II). Hwang, I., Batchelor, B. Chemosphere (2002) [Pubmed]
  17. Estimation of potential lifetime cancer risks for trihalomethanes from consuming chlorinated drinking water in Taiwan. Hsu, C.H., Jeng, W.L., Chang, R.M., Chien, L.C., Han, B.C. Environmental research. (2001) [Pubmed]
  18. Characterization of trihalomethane (THM)-induced renal dysfunction in the rat. I: Effects of THM on glomerular filtration and renal concentrating ability. Kroll, R.B., Robinson, G.D., Chung, J.H. Arch. Environ. Contam. Toxicol. (1994) [Pubmed]
  19. Hydroalcoholic extract and fractions of Davilla rugosa Poiret: effects on spontaneous motor activity and elevated plus-maze behavior. Guaraldo, L., Chagas, D.A., Konno, A.C., Korn, G.P., Pfiffer, T., Nasello, A.G. Journal of ethnopharmacology. (2000) [Pubmed]
  20. Effects of various environmental conditions on the transformation of chlorinated solvents by Methanosarcina thermophila cell exudates. Baeseman, J.L., Novak, P.J. Biotechnol. Bioeng. (2001) [Pubmed]
  21. Suicidal inactivation of haemoproteins by reductive metabolites of halomethanes: a structure-activity relationship study. Manno, M., Tolando, R., Ferrara, R., Rezzadore, M., Cazzaro, S. Toxicology (1995) [Pubmed]
  22. Differential expression of glutathione-S-transferase isoenzymes in various types of anemia in Taiwan. Chiang, W.L., Hsieh, Y.S., Yang, S.F., Lu, T.A., Chu, S.C. Clin. Chim. Acta (2007) [Pubmed]
  23. Effects of Eucommiae Cortex on osteoblast-like cell proliferation and osteoclast inhibition. Ha, H., Ho, J., Shin, S., Kim, H., Koo, S., Kim, I.H., Kim, C. Arch. Pharm. Res. (2003) [Pubmed]
  24. Relationships between characteristics of interfacial water and human bone tissues. Gun'ko, V.M., Turov, V.V., Shpilko, A.P., Leboda, R., Jablonski, M., Gorzelak, M., Jagiello-Wojtowicz, E. Colloids and surfaces. B, Biointerfaces. (2006) [Pubmed]
  25. Proton magnetic resonance spectra of 17 xi-hydroxy-17 xi-methyl-5 xi-androstane C-3 ketone and C-3 xi alcohol isomers in chloroform-d and pyridine-d5. Templeton, J.F., Jackson, C.C. Steroids (1983) [Pubmed]
  26. Nuclear magnetic resonance spectra and mosquito repellent properties of some oxazolidine derivatives of 5-methyl-4-hexenal. Taylor, W.G., Schreck, C.E. Journal of pharmaceutical sciences. (1989) [Pubmed]
  27. New Orthoquinones from the Roots of Salvia lanigera. Lee, I.S., Kaneda, N., Suttisri, R., El-Lakany, A.M., Sabri, N.N., Kinghorn, A.D. Planta Med. (1998) [Pubmed]
  28. Phase transfer of large gold nanoparticles to organic solvents with increased stability. McMahon, J.M., Emory, S.R. Langmuir : the ACS journal of surfaces and colloids (2007) [Pubmed]
  29. Auriculatin 4'-O-Glucoside: A New Prenylated Isoflavone Glycoside from Erythrina eriotricha1. Nkengfack, A.E., Meyer, M., Tempesta, M.S., Fomum, Z.T. Planta Med. (1991) [Pubmed]
  30. Chemical shift referencing in MAS solid state NMR. Morcombe, C.R., Zilm, K.W. J. Magn. Reson. (2003) [Pubmed]
  31. Repeated dosing with the peroxisome proliferator clofibrate decreases the toxicity of model hepatotoxic agents in male mice. Manautou, J.E., Silva, V.M., Hennig, G.E., Whiteley, H.E. Toxicology (1998) [Pubmed]
  32. Antinociceptive activity and chemical composition of constituents from Caragana microphylla seeds. Huo, Y., Guo, C., Zhang, Q.Y., Chen, W.S., Zheng, H.C., Rahman, K., Qin, L.P. Phytomedicine (2007) [Pubmed]
  33. Human sperm immobilization effect of Carica papaya seed extracts: an in vitro study. Lohiya, N.K., Kothari, L.K., Manivannan, B., Mishra, P.K., Pathak, N. Asian J. Androl. (2000) [Pubmed]
  34. Quantitative measurements of edge-to-face aromatic interactions by using chemical double-mutant cycles. Carver, F.J., Hunter, C.A., Jones, P.S., Livingstone, D.J., McCabe, J.F., Seward, E.M., Tiger, P., Spey, S.E. Chemistry (Weinheim an der Bergstrasse, Germany) (2001) [Pubmed]
  35. Modification of the crystal habit of celecoxib for improved processability. Banga, S., Chawla, G., Varandani, D., Mehta, B.R., Bansal, A.K. J. Pharm. Pharmacol. (2007) [Pubmed]
  36. Dechlorination of polychlorinated methanes by a sequential methanogenic-denitrifying bioreactor system. Yu, Z., Smith, G.B. Appl. Microbiol. Biotechnol. (2000) [Pubmed]
  37. Characterization of beta-bend ribbon spiral forming peptides using electronic and vibrational CD. Yoder, G., Keiderling, T.A., Formaggio, F., Crisma, M., Toniolo, C. Biopolymers (1995) [Pubmed]
  38. Characterization of trihalomethane (THM)-induced renal dysfunction in the rat. II: Relative potency of THMs in promoting renal dysfunction. Kroll, R.B., Robinson, G.D., Chung, J.H. Arch. Environ. Contam. Toxicol. (1994) [Pubmed]
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