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Chemical Compound Review

Iodmethan     iodomethane

Synonyms: Iodometano, IODOMETHANE, Joodmethaan, Methyliodid, Methyljodid, ...
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High impact information on iodomethane

  • Radioactivity incorporated into Ras by bovine brain cytosol was released by treatment with iodomethane but not with methanolic KOH indicating a thioether linkage [1].
  • The methylation was performed by treating the enzyme with excess iodomethane and monitoring the reaction by determining the concentration of unreacted cysteines in the enzyme as a function of time [2].
  • The specific binding of Mab.3C7 to R-MGMT has been compared with the protease V8 method in the detection of R-MGMT in extracts of cells treated with low dosages of methyliodide (SN2) and O6-benzylguanine [3].
  • The sulfinylcalix[4]arenes 4 were treated with iodomethane in the presence of a base to give the corresponding tetramethyl ethers 16, the structures of which in regard to the disposition of the sulfinyl groups and the conformation of the phenol units were determined by X-ray crystallography [4].
  • Imprinting of lyophilized alpha-chymotrypsin with indole or sorbitol increased the reactivity of the active-site histidine towards iodomethane [5].

Biological context of iodomethane

  • METHODS: Carbon-11 was introduced into HOMADAM by preparation of N-methyl-2-(2'-amino-4'-hydroxymethylphenylthio)benzylamine followed by alkylation with carbon-11 iodomethane [6].
  • The fumigant methyl iodide (MeI, iodomethane) is considered a promising alternative to methyl bromide (MeBr) for soil-borne pest control in high-cash-value crops [7].
  • Analysis of reaction kinetics and initial products suggests that the reaction is SN2 nucleophilic substitution for MeI and 1,3-D but likely reductive dehalogenation for CP [8].

Anatomical context of iodomethane

  • Thirty minutes prior to the start of the infusion, 20 mg/kg iodomethane, dissolved in oliver oil, was given into the duodenum [9].
  • Since the localization of opiate receptor responses to inside or outside the BBB depended upon the relative ability of nalmefene HCl and nalmefene methyliodide to penetrate the BBB, initial studies were conducted to document that nalmefene methyliodide does not block opiate receptors inside the central nervous system [10].

Associations of iodomethane with other chemical compounds

  • The procedure involves extraction of plasma lipids with hexane, methylation with iodomethane (CH(3)I) to form fatty acid methyl esters (FAME), and subsequent purification of FAME by solid phase extraction (SPE) chromatography [11].
  • UV spectroscopic studies of methyl derivatives 7 and 8a as well as the parent heterocycle 6 showed that protonation of the latter occurred at N1, while methylation with iodomethane proceeded at N6 and N8 [12].
  • After evaporation to dryness the drug and its metabolite were derivatized by methylation with iodomethane in tetrabutylammonium hydroxide-dimethyl sulphoxide (DMSO) [13].
  • The iodomethane and 2-iodopropane are extracted into xylene, the extract is diluted with methanol, and the analytes are separated and assayed by gradient elution using a reversed-phase C18 column [14].
  • These substituents were introduced by dilithiation of 3-(4-methoxybenzylidineamino)-2-piperidinone with lithium diisopropylamide followed by regiospecific alkylation at C-3 with iodomethane or ethyl bromoacetate [15].

Gene context of iodomethane

  • When unconjugated BSP was infused, the excretion of total BSP (unconjugated plus conjugated) was markedly lower in the iodomethane-treated group than in the control [9].
  • We observed that basal PRL levels were reduced by nalmefene HCl but not by nalmefene methyliodide indicating that basal PRL secretion is influenced by opioid neurons inside the BBB [10].
  • The selective, reversible acetylcholinesterase inhibitor 5,7-Dihydro-7-methyl-3- [2-[1-(phenylmethyl]-4-piperidinyl]ethyl]-6H-pyrrolo[3,2-f]-1,2-benzisoxazol3-6-one (CP-126,998) was labeled with C-11 iodomethane via base-promoted alkylation of the lactam nitrogen [16].

Analytical, diagnostic and therapeutic context of iodomethane


  1. Polyisoprenylation of Ras in vitro by a farnesyl-protein transferase. Schaber, M.D., O'Hara, M.B., Garsky, V.M., Mosser, S.C., Bergstrom, J.D., Moores, S.L., Marshall, M.S., Friedman, P.A., Dixon, R.A., Gibbs, J.B. J. Biol. Chem. (1990) [Pubmed]
  2. Protection of phosphoglycerate kinase against in vitro aging by selective cysteine methylation. Cook, L.L., Gafni, A. J. Biol. Chem. (1988) [Pubmed]
  3. Conformational change in human DNA repair enzyme O6-methylguanine-DNA methyltransferase upon alkylation of its active site by SN1 (indirect-acting) and SN2 (direct-acting) alkylating agents: breaking a "salt-link". Oh, H.K., Teo, A.K., Ali, R.B., Lim, A., Ayi, T.C., Yarosh, D.B., Li, B.F. Biochemistry (1996) [Pubmed]
  4. Synthesis of all stereoisomers of sulfinylcalix[4]arenes. Morohashi, N., Katagiri, H., Iki, N., Yamane, Y., Kabuto, C., Hattori, T., Miyano, S. J. Org. Chem. (2003) [Pubmed]
  5. Imprinting of lyophilized alpha-chymotrypsin affects the reactivity of the active-site imidazole. Stewart, N.A., Taralp, A., Kaplan, H. Biochem. Biophys. Res. Commun. (1997) [Pubmed]
  6. Carbon-11 HOMADAM: a novel PET radiotracer for imaging serotonin transporters. Jarkas, N., Votaw, J.R., Voll, R.J., Williams, L., Camp, V.M., Owens, M.J., Purselle, D.C., Bremner, J.D., Kilts, C.D., Nemeroff, C.B., Goodman, M.M. Nucl. Med. Biol. (2005) [Pubmed]
  7. Accelerated degradation of methyl iodide by agrochemicals. Zheng, W., Papiernik, S.K., Guo, M., Yates, S.R. J. Agric. Food Chem. (2003) [Pubmed]
  8. Dehalogenation of halogenated fumigants by polysulfide salts. Bondarenko, S., Zheng, W., Yates, S.R., Gan, J. J. Agric. Food Chem. (2006) [Pubmed]
  9. Excretion of sulfobromophthalein in rats with iodomethane-induced depletion of hepatic glutathione. Schulze, P.J., Czok, G., Borck, H.U. Naunyn Schmiedebergs Arch. Pharmacol. (1976) [Pubmed]
  10. Evaluation of the sites of opioid influence on anterior pituitary hormone secretion using a quaternary opiate antagonist. Simpkins, J.W., Swager, D., Millard, W.J. Neuroendocrinology (1991) [Pubmed]
  11. Validation of a new procedure to determine plasma fatty acid concentration and isotopic enrichment. Patterson, B.W., Zhao, G., Elias, N., Hachey, D.L., Klein, S. J. Lipid Res. (1999) [Pubmed]
  12. Synthesis of quaternised 2-aminopyrimido[4,5-d]pyrimidin-4(3H)-ones and their biological activity with dihydrofolate reductase. Gebauer, M.G., McKinlay, C., Gready, J.E. European journal of medicinal chemistry. (2003) [Pubmed]
  13. Testing human blood for cannabis by GC-MS. Kintz, P., Cirimele, V. Biomed. Chromatogr. (1997) [Pubmed]
  14. Alternative liquid chromatographic method for determination of the methoxyl and 2-hydroxypropoxyl content in cellulose ether derivatives. Rashan, J., Chen, R., Zelesky, T., Sekulic, S. Journal of AOAC International. (2003) [Pubmed]
  15. Synthesis of 2-methyl and 2-carboxymethyl derivatives of ornithine and arginine. Unson, C.G., Erickson, B.W. Int. J. Pept. Protein Res. (1983) [Pubmed]
  16. Radiosynthesis and mouse brain distribution studies of [11C] CP-126,998: a PET ligand for in vivo study of acetylcholinesterase. Musachio, J.L., Flesher, J.E., Scheffel, U.A., Rauseo, P., Hilton, J., Mathews, W.B., Ravert, H.T., Dannals, R.F., Frost, J.J. Nucl. Med. Biol. (2002) [Pubmed]
  17. Improved peptide detection with matrix-assisted laser desorption/ionization mass spectrometry by trimethylation of amino groups. Stewart, N.A., Pham, V.T., Choma, C.T., Kaplan, H. Rapid Commun. Mass Spectrom. (2002) [Pubmed]
  18. Substrate characterization of the Saccharomyces cerevisiae protein farnesyltransferase and type-I protein geranylgeranyltransferase. Caplin, B.E., Hettich, L.A., Marshall, M.S. Biochim. Biophys. Acta (1994) [Pubmed]
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