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Record Information
Version3.6
Creation Date2006-02-23 13:09:54 UTC
Update Date2014-12-01 23:15:54 UTC
HMDB IDHMDB01875
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethanol
DescriptionIt is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (Wikipedia). Methanol is responsible for accidental, suicidal, and epidemic poisonings, resulting in death or permanent sequelae. Toxicity is due to the metabolic products of alcohol dehydrogenase (ADH) and aldehyde dehydrogenase. (PMID 15627163 ). The rapid and accurate diagnosis of toxic alcohol poisoning due to methanol (methyl alcohol) is paramount in preventing serious adverse outcomes. The quantitative measurement of specific serum levels of methanol using gas chromatography is expensive, time consuming and generally only available at major tertiary-care facilities. (PMID 15862085 ).
Structure
Thumb
Synonyms
  1. Alcool methylique
  2. Alcool metilico
  3. Carbinol
  4. CH3OH
  5. Colonial spirit
  6. Columbian spirit
  7. Columbian spirits
  8. Hydroxymethane
  9. Metanolo
  10. Methanol
  11. Methanol-water mixture
  12. Methyl alcohol
  13. Methyl hydroxide
  14. Methylalkohol
  15. Methylol
  16. Metylowy alkohol
  17. Monohydroxymethane
  18. Pyro alcohol
  19. Pyroxylic spirit
  20. Spirit of wood
  21. Wood alcohol
  22. Wood naphtha
  23. Wood spirit
Chemical FormulaCH4O
Average Molecular Weight32.0419
Monoisotopic Molecular Weight32.02621475
IUPAC Namemethanol
Traditional Namemethanol
CAS Registry Number67-56-1
SMILES
CO
InChI Identifier
InChI=1S/CH4O/c1-2/h2H,1H3
InChI KeyOKKJLVBELUTLKV-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlcohols and Polyols
Sub ClassPrimary Alcohols
Other Descriptors
  • Aliphatic Acyclic Compounds
  • a short-chain alcohol(Cyc)
  • alkyl alcohol(ChEBI)
  • primary alcohol(ChEBI)
Substituents
  • N/A
Direct ParentPrimary Alcohols
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Toxin/Pollutant
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Extracellular
  • Lysosome
  • Endoplasmic reticulum
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-97.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
LogP-0.77HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility519.0ALOGPS
logP-1.4ALOGPS
logP-0.52ChemAxon
logS1.21ALOGPS
pKa (Strongest Acidic)15.78ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity8.26 m3·mol-1ChemAxon
Polarizability3.38 Å3ChemAxon
Spectra
SpectraMS/MSMS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Lysosome
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Adrenal Gland
  • Brain
  • Erythrocyte
  • Fibroblasts
  • Hair
  • Intestine
  • Kidney
  • Liver
  • Myelin
  • Nerve Cells
  • Pancreas
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified468.4 (32.0 - 936.7) uMAdult (>18 years old)Not Specified
Normal
    • Baselt, RC. Dispo...
details
BloodDetected and Quantified47.2 +/- 10.3 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified77.4 +/- 16.3 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified44 +/- 36 uMNot SpecifiedBothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified5 (1-17) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified11 (<1-142) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified12 (<1-115) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified8 (<1-22) uMAdult (>18 years old)Female
Normal
details
SalivaDetected and Quantified1-100 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified1-155 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified133.36 +/- 84.57 uMAdult (>18 years old)BothNormal
    • Dame, ZT. et al. ...
details
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified37 (10-117) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified227.9 +/- 112.4 uMAdult (>18 years old)Both
Alcoholism
details
BloodDetected and Quantified81.5 +/- 55.2 uMAdult (>18 years old)Not SpecifiedHeart Transplant details
BloodDetected and Quantified1548.0 (624.0-5557.0) uMAdult (>18 years old)BothAlcohol intoxication details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Diarrhea-predominant IBS
details
UrineDetected and Quantified15427.0 +/- 10168.0 umol/mmol creatinineAdult (>18 years old)MaleDrunk driver details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. Pubmed: 2779169
  2. Jones AW, Helander A: Changes in the concentrations of ethanol, methanol and metabolites of serotonin in two successive urinary voids from drinking drivers. Forensic Sci Int. 1998 May 11;93(2-3):127-34. Pubmed: 9717263
  3. Jones AW, Lowinger H: Relationship between the concentration of ethanol and methanol in blood samples from Swedish drinking drivers. Forensic Sci Int. 1988 Jun;37(4):277-85. Pubmed: 3410397
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00536
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008124
KNApSAcK IDNot Available
Chemspider ID864
KEGG Compound IDC00132
BioCyc ID3-OH-BENZYL-ALCOHOL
BiGG ID33974
Wikipedia LinkMethanol
NuGOwiki LinkHMDB01875
Metagene LinkHMDB01875
METLIN ID4201
PubChem Compound887
PDB IDMOH
ChEBI ID17790
References
Synthesis ReferenceCummings, Donald Ray. Process for production of methanol from a methane gas stream. PCT Int. Appl. (2007), 21pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  2. Nagasawa H, Wada M, Koyama S, Kawanami T, Kurita K, Kato T: [A case of methanol intoxication with optic neuropathy visualized on STIR sequence of MR images] Rinsho Shinkeigaku. 2005 Jul;45(7):527-30. Pubmed: 16119839
  3. Ferrari LA, Arado MG, Nardo CA, Giannuzzi L: Post-mortem analysis of formic acid disposition in acute methanol intoxication. Forensic Sci Int. 2003 Apr 23;133(1-2):152-8. Pubmed: 12742704
  4. Avella J, Briglia E, Harleman G, Lehrer M: Percutaneous absorption and distribution of methanol in a homicide. J Anal Toxicol. 2005 Oct;29(7):734-7. Pubmed: 16419410
  5. Bogdanov-Berezovsky A, Glesinger R, Kachko L, Arbel E, Rosenberg L, Grossman N: Accreditation of skin from a methanol-poisoned victim for banking and grafting. Transplantation. 2002 Jun 27;73(12):1913-7. Pubmed: 12131687
  6. Heinig K, Henion J: Determination of carnitine and acylcarnitines in biological samples by capillary electrophoresis-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Dec 10;735(2):171-88. Pubmed: 10670733
  7. Kaphalia BS, Carr JB, Ansari GA: Increased endobiotic fatty acid methyl esters following exposure to methanol. Fundam Appl Toxicol. 1995 Dec;28(2):264-73. Pubmed: 8835236
  8. Batterman SA, Franzblau A, Zhou N: Airborne emissions at skin surfaces: a potential biological exposure index. Int Arch Occup Environ Health. 1996;68(4):268-74. Pubmed: 8738358
  9. Vassiliadis J, Graudins A, Dowsett RP: Triethylene glycol poisoning treated with intravenous ethanol infusion. J Toxicol Clin Toxicol. 1999;37(6):773-6. Pubmed: 10584590
  10. Lee XP, Kumazawa T, Kondo K, Sato K, Suzuki O: Analysis of methanol or formic acid in body fluids by headspace solid-phase microextraction and capillary gas chromatography. J Chromatogr B Biomed Sci Appl. 1999 Oct 29;734(1):155-62. Pubmed: 10574201
  11. Jose N, Ajith TA, Janardhanan KK: Methanol extract of the oyster mushroom, Pleurotus florida, inhibits inflammation and platelet aggregation. Phytother Res. 2004 Jan;18(1):43-6. Pubmed: 14750200
  12. Comoglu S, Ozen B, Ozbakir S: Methanol intoxication with bilateral basal ganglia infarct. Australas Radiol. 2001 Aug;45(3):357-8. Pubmed: 11531765
  13. Yu C, Shin YG, Chow A, Li Y, Kosmeder JW, Lee YS, Hirschelman WH, Pezzuto JM, Mehta RG, van Breemen RB: Human, rat, and mouse metabolism of resveratrol. Pharm Res. 2002 Dec;19(12):1907-14. Pubmed: 12523673
  14. Keum YS, Park KK, Lee JM, Chun KS, Park JH, Lee SK, Kwon H, Surh YJ: Antioxidant and anti-tumor promoting activities of the methanol extract of heat-processed ginseng. Cancer Lett. 2000 Mar 13;150(1):41-8. Pubmed: 10755385
  15. Megarbane B, Borron SW, Baud FJ: Current recommendations for treatment of severe toxic alcohol poisonings. Intensive Care Med. 2005 Feb;31(2):189-95. Epub 2004 Dec 31. Pubmed: 15627163
  16. Purssell RA, Lynd LD, Koga Y: The use of the osmole gap as a screening test for the presence of exogenous substances. Toxicol Rev. 2004;23(3):189-202. Pubmed: 15862085

Enzymes

General function:
Involved in peroxidase activity
Specific function:
May contribute to airway host defense against infection.
Gene Name:
LPO
Uniprot ID:
P22079
Molecular weight:
70983.6
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
Reactions
Methanol + Hydrogen peroxide → Formaldehyde + Waterdetails
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
General function:
Involved in peroxidase activity
Specific function:
Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis.
Gene Name:
EPX
Uniprot ID:
P11678
Molecular weight:
81039.5
General function:
Involved in catalase activity
Specific function:
Occurs in almost all aerobically respiring organisms and serves to protect cells from the toxic effects of hydrogen peroxide. Promotes growth of cells including T-cells, B-cells, myeloid leukemia cells, melanoma cells, mastocytoma cells and normal and transformed fibroblast cells.
Gene Name:
CAT
Uniprot ID:
P04040
Molecular weight:
59755.82
Reactions
Methanol + Hydrogen peroxide → Formaldehyde + Waterdetails
General function:
Not Available
Specific function:
Demethylates proteins that have been reversibly carboxymethylated. Demethylates PPP2CB (in vitro) and PPP2CA. Binding to PPP2CA displaces the manganese ion and inactivates the enzyme.
Gene Name:
PPME1
Uniprot ID:
Q9Y570
Molecular weight:
43869.905
Reactions
[Phosphatase 2A protein]-leucine methyl ester + Water → [phosphatase 2A protein]-leucine + Methanoldetails