The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

carbinol     methanol

Synonyms: Carbonal, Metanolo, Methylol, Metanol, MetOH, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of methanol

  • 1. Alcohol drinkers and cigarette smokers, especially those 40 years of age and older, are at very high risk for the development of upper aerodigestive tract and lung squamous carcinomas [1].
  • The probable cause of abnormal LTs was excessive alcohol in 45.6%, HCV in 18.6%, HBV in 1%, alcohol plus HCV and/or HBV in 8.8%, and rare diseases in 2% [2].
  • RESULTS: Silanediol analogs of a carbinol-based inhibitor of the HIV protease were prepared as single enantiomers, with up to six stereogenic centers [3].
  • Reduced phototoxicity of a fluoroquinolone antibacterial agent with a methoxy group at the 8 position in mice irradiated with long-wavelength UV light [4].
  • Melatonin (100 mg/kg body weight, BW) was administered 6 hr (a) after a single dose of CCl4 (intragastrically 0. 66 mL/kg BW diluted 1:1 v/v with corn oil); (b) a single dose of AA (intraperitonealy, 0.62 mmol/kg BW 1:50 v/v in 0.9% saline solution); and (c) a combination of the above substances [5].

Psychiatry related information on methanol

  • A review of the literature on the positive psychological benefits of light and moderate alcohol consumption suggests the following: (1) Alcohol in moderate amounts is effective in reducing stress [6].
  • Presentations included (1) Alcohol use outcomes at 1 year among adolescents in the drug abuse treatment outcomes studies (DATOS-A), by Christine E [7].
  • BACKGROUND: Primary alcohol abuse-prevention services delivered to adolescents are inadequate, despite the fact that alcohol abuse is a major health problem [8].
  • METHODS: Four subject groups were tested: (1) alcohol-dependent patients with (n = 28) and (2) alcohol-dependent patients without (n = 28), a history of conduct disorder and (3) normal controls with (n = 10) and (4) normal controls without (n = 30) a history of conduct disorder [9].
  • During the period of adaptation to the test cage ANA rats of both sexes showed increased locomotor activity compared to the corresponding sex of the AA rats [10].

High impact information on methanol

  • Unusual response of DDT-resistant houseflies to carbinol analogues of DDT [11].
  • The three-dimensional structure of human beta 1 beta 1 alcohol dehydrogenase (ADH; EC complexed with NAD+ has been determined by x-ray crystallography to 3.0-A resolution [12].
  • Inhibition of lipolysis with beta-pyridyl carbinol almost abolished FFAu and reduced MVO2 significantly [13].
  • AFP mRNA expression was also examined in an acute AA and CCl4 injury [14].
  • We confirmed the presence of class 1 alcohol dehydrogenase activity and isoenzymes in the cytosol of cultured fat-storing cells in their second passage [15].

Chemical compound and disease context of methanol


Biological context of methanol

  • This result indicates not only that a methoxy group in the 2-position is recognized more strictly than the 3-position by the binding site but also that the side chain structure does not affect binding of the quinol ring moiety [21].
  • Thioether analogs with sulfhydryl arylation capacity, especially those with a hydroxy (Cpd 5) or a methoxy group at the end of the side chain, induced protein-tyrosine phosphorylation, but non-arylating analogs, such as those with an all-carbon or O-ether side chain, did not [22].
  • Confirmation and fine mapping of the chromosome 1 alcohol dependence risk locus [23].
  • We present here the results of this study in terms of structure-activity relationships focusing on the influence of the acetamidoethyl side chain, the methoxy group, and the indole heterocycle [24].
  • The mo4C.G base-pair is of the wobble type, with mo4C in the imino form, and the methoxy group in the syn configuration [25].

Anatomical context of methanol

  • Thus, compounds bearing in the 7-position a methyl or a methoxy group or devoid of a substituent in this position, and bearing an ethyl, an isopropyl, or a cyclobutylamino group in the 3-position were found to be potent and selective inhibitors of insulin release from rat pancreatic B-cells (i.e. 10a, 10b, 12b, 12d, 22c) [26].
  • The 2-phenyl-1,8-naphthyridin-4-ones (44-49) with a methoxy group at the 3'-position showed potent cytotoxicity against most tumor cell lines with GI50 values in the low micromolar to nanomolar concentration range in the National Cancer Institute's 60 human tumor cell line in vitro screen [27].
  • Carbinol-carbon stereochemistry did not appreciably influence stereoselectivity at the 4-position in the metabolism of these compounds by mouse lung microsomes or p450 2A5 but did influence the regiochemistry of metabolism [28].
  • Using bufuralol-1'-hydroxylation to carbinol to optimize the procedure, 3 cytochrome P450 isozymes (P450A, P450buf, P450C) were purified to apparent electrophoretic homogeneity from human liver microsomes [29].
  • Guinea-pig papillary muscles were superfused with Tyrode solution at 30 degrees C and exposed to harmine or its analogue harmane, in which the methoxy group has been removed from the molecule [30].

Associations of methanol with other chemical compounds

  • The results of spectroscopic experiments clarified that this enhanced reactivity can be attributed to the intramolecular hydrogen-bonding interaction between the N-H of the imide and the methoxy group of the benzamide moiety [31].
  • Replacement of the C-4' hydroxyl group with a methoxy group raised the IC(50) for PDE3 and PDE1, yet only slightly changed the IC(50) for PDE4 [32].
  • Substitution at the 4-position of the phenyl ring was restricted to a methoxy group, probably due to unfavorable steric interactions of larger groups with the binding site [33].
  • Codeine binds to P450 2D6 so that the methoxy group is directly above the A ring of the heme, while the basic nitrogen interacts with the carboxylate of aspartate 301 [34].
  • The stereoselective metabolism of (-)- and (+)-bufuralol to carbinol by purified P450buf [(-)/(+) ratio: 0.13] was strikingly different from that in the microsomes of either an extensive [(-)/(+) ratio: 0.4] or poor metabolizer [(-)/(+) ratio: 0.83] of bufuralol [29].
  • This implies that ethene formation is mechanistically separated from the formation of higher alkenes, an insight of utmost importance for understanding and possibly controlling the ethene/propene selectivity in methanol-to-alkenes catalysis [35].
  • In that case, the major product of the reaction was an ion of stoichiometry [Nb, O3, H2]- arising from the formal dehydrogenation of methanol to formaldehyde [36].

Gene context of methanol

  • Addition of a methoxy group to amphetamine in the 2-position also increased the affinity for CYP2D6 (Ki = 11.5 microM) [37].
  • The production of carbaryl methylol was primarily the result of metabolism by CYP2B6 [38].
  • We measured plasma LCAT, CETP and PLTP activities with exogenous substrate assays, as well as lipoproteins and HDL lipids in 6 alcohol-abstaining men, 18 matched men who used < or = 1 and 18 men who used > or = 1 alcohol-containing drinks per day [39].
  • These results indicate that the activation of striatal M3-like muscarinic receptors and beta-adrenoceptors, but not M2-like muscarinic receptors and alpha-adrenoceptors, modulates directly corticostriatal glutamatergic neurotransmission [40].
  • Xylitol dehydrogenase encoded by gene XYL2 from Pichia stipitis is a member of the medium-chain alcohol dehydrogenase family, as evidenced by the domain organization and a distant homology (24% residue identity with the human class I gamma 1 alcohol dehydrogenase) [41].

Analytical, diagnostic and therapeutic context of methanol

  • The presentations and presenters were (1) Alcohol Seeking and Self-Administration in Rats: The Role of Serotonin Activity, by Cristine L [42].
  • In patient 1 alcohol intolerance persisted during the whole course of disease, while in patient 2 all symptoms including alcohol intolerance disappeared after treatment with prednisolone and vincristine [43].
  • The non-radioactive counterparts of the desired SPECT- and PET-radiotracers were synthesized as reference compounds [e.g., 8f, 8g, 8h and 8l as the non-radioactive analogues of the radioiodinated SPECT radioligands, 8e and 8h as the non-radioactive compounds of C-11 labelled PET-tracers (C-11 in the methoxy group)] [44].
  • Estimated deaths attributed to each factor were: (1) alcohol use, 366 606; (2) not wearing a seat belt, 259 239; (3) lack of an air bag, 31 377; (4) no motorcycle helmet, 12 095; (5) no bicycle helmet, 10 552 [45].
  • OBJECTIVE: To estimate the contributions of five risk factors to changes in US traffic crash mortality: (1) alcohol use by drivers and pedestrians, (2) not wearing a seat belt, (3) lack of an air bag, (4) not wearing a motorcycle helmet, and (5) not wearing a bicycle helmet [45].


  1. Early diagnosis of asymptomatic oral and oropharyngeal squamous cancers. Mashberg, A., Samit, A. CA: a cancer journal for clinicians. (1995) [Pubmed]
  2. Prevalence and etiology of altered liver tests: a population-based survey in a Mediterranean town. Pendino, G.M., Mariano, A., Surace, P., Caserta, C.A., Fiorillo, M.T., Amante, A., Bruno, S., Mangano, C., Polito, I., Amato, F., Cotichini, R., Stroffolini, T., Mele, A. Hepatology (2005) [Pubmed]
  3. Drug design with a new transition state analog of the hydrated carbonyl: silicon-based inhibitors of the HIV protease. Chen, C.A., Sieburth, S.M., Glekas, A., Hewitt, G.W., Trainor, G.L., Erickson-Viitanen, S., Garber, S.S., Cordova, B., Jeffry, S., Klabe, R.M. Chem. Biol. (2001) [Pubmed]
  4. Reduced phototoxicity of a fluoroquinolone antibacterial agent with a methoxy group at the 8 position in mice irradiated with long-wavelength UV light. Marutani, K., Matsumoto, M., Otabe, Y., Nagamuta, M., Tanaka, K., Miyoshi, A., Hasegawa, T., Nagano, H., Matsubara, S., Kamide, R. Antimicrob. Agents Chemother. (1993) [Pubmed]
  5. Therapeutic value of melatonin in an experimental model of liver injury and regeneration. Sigala, F., Theocharis, S., Sigalas, K., Markantonis-Kyroudis, S., Papalabros, E., Triantafyllou, A., Kostopanagiotou, G., Andreadou, I. J. Pineal Res. (2006) [Pubmed]
  6. The psychological benefits of moderate alcohol consumption: a review of the literature. Baum-Baicker, C. Drug and alcohol dependence. (1985) [Pubmed]
  7. Course of alcohol problems in treated adolescents. Chung, T., Martin, C.S., Grella, C.E., Winters, K.C., Abrantes, A.M., Brown, S.A. Alcohol. Clin. Exp. Res. (2003) [Pubmed]
  8. Physicians' attitudes and beliefs concerning alcohol abuse prevention in adolescents. Marcell, A.V., Halpern-Felsher, B., Coriell, M., Millstein, S.G. American journal of preventive medicine. (2002) [Pubmed]
  9. Effects of the history of conduct disorder on the Iowa Gambling Tasks. Kim, Y.T., Lee, S.J., Kim, S.H. Alcohol. Clin. Exp. Res. (2006) [Pubmed]
  10. Audiogenic immobility reaction and open-field behavior in AA and ANA rat lines. Fahlke, C., Eriksson, C.J., Hård, E. Alcohol (1993) [Pubmed]
  11. Unusual response of DDT-resistant houseflies to carbinol analogues of DDT. Sawicki, R.M. Nature (1978) [Pubmed]
  12. Structure of human beta 1 beta 1 alcohol dehydrogenase: catalytic effects of non-active-site substitutions. Hurley, T.D., Bosron, W.F., Hamilton, J.A., Amzel, L.M. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  13. The effect of free fatty acids on myocardial oxygen consumption during atrial pacing and catecholamine infusion in man. Simonsen, S., Kjekshus, J.K. Circulation (1978) [Pubmed]
  14. Hepatic oval cell activation in response to injury following chemically induced periportal or pericentral damage in rats. Petersen, B.E., Zajac, V.F., Michalopoulos, G.K. Hepatology (1998) [Pubmed]
  15. Effects of ethanol on prostanoid production by liver fat-storing cells. Flisiak, R., Baraona, E., Li, J., Lieber, C.S. Hepatology (1993) [Pubmed]
  16. New pathway for long-chain n-alkane synthesis via 1-alcohol in Vibrio furnissii M1. Park, M.O. J. Bacteriol. (2005) [Pubmed]
  17. Substrate range of acetohydroxy acid synthase I from Escherichia coli in the stereoselective synthesis of alpha-hydroxy ketones. Engel, S., Vyazmensky, M., Berkovich, D., Barak, Z., Chipman, D.M. Biotechnol. Bioeng. (2004) [Pubmed]
  18. Bacterial chemistry. VI. Biological activities and cytotoxicity of 1,3-dihydro-2H-indol-2-one derivatives. Haun, M., Pereira, M.F., Hoffmann, M.E., Joyas, A., Campos, V., Filardi, L.D., de Castro, S.L., Duran, N. Biol. Res. (1992) [Pubmed]
  19. Studies in sclerotherapy: I. Comparison of sodium tetradecyl sulphate (STS) with absolute alcohol (AA) as sclerosants in the treatment of esophageal varices. Chawla, Y., Dilawari, J.B. J. Clin. Gastroenterol. (1990) [Pubmed]
  20. 2,4-diaminoanisole-induced thyroid pigmentation in rats inhibited by m-phenylenediamine. Evarts, R.P., Brown, C.A. Toxicol. Lett. (1981) [Pubmed]
  21. Probing substrate binding site of the Escherichia coli quinol oxidases using synthetic ubiquinol analogues. Sakamoto, K., Miyoshi, H., Takegami, K., Mogi, T., Anraku, Y., Iwamura, H. J. Biol. Chem. (1996) [Pubmed]
  22. Inhibition of hepatoma cell growth in vitro by arylating and non-arylating K vitamin analogs. Significance of protein tyrosine phosphatase inhibition. Nishikawa, Y., Wang, Z., Kerns, J., Wilcox, C.S., Carr, B.I. J. Biol. Chem. (1999) [Pubmed]
  23. Confirmation and fine mapping of the chromosome 1 alcohol dependence risk locus. Lappalainen, J., Kranzler, H.R., Petrakis, I., Somberg, L.K., Page, G., Krystal, J.H., Gelernter, J. Mol. Psychiatry (2004) [Pubmed]
  24. Structure-activity relationships in a series of melatonin analogues with the low-density lipoprotein oxidation model. Gozzo, A., Lesieur, D., Duriez, P., Fruchart, J.C., Teissier, E. Free Radic. Biol. Med. (1999) [Pubmed]
  25. Molecular and crystal structure of d(CGCGmo4CG): N4-methoxycytosine.guanine base-pairs in Z-DNA. Van Meervelt, L., Moore, M.H., Lin, P.K., Brown, D.M., Kennard, O. J. Mol. Biol. (1990) [Pubmed]
  26. Effect on K(ATP) channel activation properties and tissue selectivity of the nature of the substituent in the 7- and the 3-position of 4H-1,2,4-benzothiadiazine 1,1-dioxides. Boverie, S., Antoine, M.H., Somers, F., Becker, B., Sebille, S., Ouedraogo, R., Counerotte, S., Pirotte, B., Lebrun, P., de Tullio, P. J. Med. Chem. (2005) [Pubmed]
  27. Antitumor agents. 174. 2',3',4',5,6,7-Substituted 2-phenyl-1,8-naphthyridin-4-ones: their synthesis, cytotoxicity, and inhibition of tubulin polymerization. Chen, K., Kuo, S.C., Hsieh, M.C., Mauger, A., Lin, C.M., Hamel, E., Lee, K.H. J. Med. Chem. (1997) [Pubmed]
  28. Synthesis of stereospecifically deuterated 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) iastereomers and metabolism by A/J mouse lung microsomes and cytochrome p450 2A5. Jalas, J.R., Hecht, S.S. Chem. Res. Toxicol. (2003) [Pubmed]
  29. Debrisoquine-type polymorphism of drug oxidation: purification from human liver of a cytochrome P450 isozyme with high activity for bufuralol hydroxylation. Gut, J., Gasser, R., Dayer, P., Kronbach, T., Catin, T., Meyer, U.A. FEBS Lett. (1984) [Pubmed]
  30. Effects of harmala alkaloids on transmembrane potentials of guinea-pig papillary muscles. Carpentier, R.G. Br. J. Pharmacol. (1982) [Pubmed]
  31. Thiourea-catalyzed asymmetric michael addition of activated methylene compounds to alpha,beta-unsaturated imides: dual activation of imide by intra- and intermolecular hydrogen bonding. Inokuma, T., Hoashi, Y., Takemoto, Y. J. Am. Chem. Soc. (2006) [Pubmed]
  32. Differential inhibition of multiple cAMP phosphodiesterase isozymes by isoflavones and tyrphostins. Nichols, M.R., Morimoto, B.H. Mol. Pharmacol. (2000) [Pubmed]
  33. Novel selective PDE4 inhibitors. 2. Synthesis and structure-activity relationships of 4-aryl-substituted cis-tetra- and cis-hexahydrophthalazinones. Van der Mey, M., Hatzelmann, A., Van Klink, G.P., Van der Laan, I.J., Sterk, G.J., Thibaut, U., Ulrich, W.R., Timmerman, H. J. Med. Chem. (2001) [Pubmed]
  34. A model for human cytochrome P450 2D6 based on homology modeling and NMR studies of substrate binding. Modi, S., Paine, M.J., Sutcliffe, M.J., Lian, L.Y., Primrose, W.U., Wolf, C.R., Roberts, G.C. Biochemistry (1996) [Pubmed]
  35. Conversion of methanol into hydrocarbons over zeolite H-ZSM-5: ethene formation is mechanistically separated from the formation of higher alkenes. Svelle, S., Joensen, F., Nerlov, J., Olsbye, U., Lillerud, K.P., Kolboe, S., Bjørgen, M. J. Am. Chem. Soc. (2006) [Pubmed]
  36. Gas-phase reactivity of metavanadate [VO3]- towards methanol and ethanol: experiment and theory. Waters, T., Wedd, A.G., O'Hair, R.A. Chemistry (2007) [Pubmed]
  37. Interactions of amphetamine analogs with human liver CYP2D6. Wu, D., Otton, S.V., Inaba, T., Kalow, W., Sellers, E.M. Biochem. Pharmacol. (1997) [Pubmed]
  38. In vitro metabolism of carbaryl by human cytochrome P450 and its inhibition by chlorpyrifos. Tang, J., Cao, Y., Rose, R.L., Hodgson, E. Chem. Biol. Interact. (2002) [Pubmed]
  39. Higher high density lipoprotein cholesterol associated with moderate alcohol consumption is not related to altered plasma lecithin:cholesterol acyltransferase and lipid transfer protein activity levels. Riemens, S.C., van Tol, A., Hoogenberg, K., van Gent, T., Scheek, L.M., Sluiter, W.J., Dullaart, R.P. Clin. Chim. Acta (1997) [Pubmed]
  40. Activation of muscarinic M3-like receptors and beta-adrenoceptors, but not M2-like muscarinic receptors or alpha-adrenoceptors, directly modulates corticostriatal neurotransmission in vitro. Niittykoski, M., Ruotsalainen, S., Haapalinna, A., Larson, J., Sirviö, J. Neuroscience (1999) [Pubmed]
  41. Dual relationships of xylitol and alcohol dehydrogenases in families of two protein types. Persson, B., Hallborn, J., Walfridsson, M., Hahn-Hägerdal, B., Keränen, S., Penttilä, M., Jörnvall, H. FEBS Lett. (1993) [Pubmed]
  42. Building bridges: the transdisciplinary study of craving from the animal laboratory to the lamppost. Monti, P.M., Tidey, J., Czachowski, C.L., Grant, K.A., Rohsenow, D.J., Sayette, M., Maners, N., Pierre, P. Alcohol. Clin. Exp. Res. (2004) [Pubmed]
  43. Alcohol intolerance in the hypereosinophilic syndrome. Lederman, J., Hasselbalch, H., Hippe, E. Alcohol. Clin. Exp. Res. (1988) [Pubmed]
  44. Design of new beta1-selective adrenoceptor ligands as potential radioligands for in vivo imaging. Kopka, K., Wagner, S., Riemann, B., Law, M.P., Puke, C., Luthra, S.K., Pike, V.W., Wichter, T., Schmitz, W., Schober, O., Schäfers, M. Bioorg. Med. Chem. (2003) [Pubmed]
  45. Changes in traffic crash mortality rates attributed to use of alcohol, or lack of a seat belt, air bag, motorcycle helmet, or bicycle helmet, United States, 1982-2001. Cummings, P., Rivara, F.P., Olson, C.M., Smith, K.M. Inj. Prev. (2006) [Pubmed]
WikiGenes - Universities