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Record Information
Version1.0
Creation Date2009-03-06 18:58:29 UTC
Update Date2016-11-09 01:08:12 UTC
Accession NumberCHEM000253
Identification
Common NameArsenocholine
ClassSmall Molecule
DescriptionArsenocholine is found in crustaceans. Claimed isolation from marine crustacea (prawns) Arsenocholine belongs to the family of Primary Alcohols. These are compounds comprising the primary alcohol functional group, with the general strucuture RCOH (R=alkyl, aryl).
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Arsenic Compound
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Organometallic
Chemical Structure
Thumb
Synonyms
ValueSource
(2-Hydroxyethyl)trimethylarsoniumChEBI
(2-Hydroxyethyl)trimethyl-arsoniumHMDB
Chemical FormulaC5H14AsO
Average Molecular Mass165.085 g/mol
Monoisotopic Mass165.026 g/mol
CAS Registry Number39895-81-3
IUPAC Name(2-hydroxyethyl)trimethylarsanium
Traditional Name(2-hydroxyethyl)trimethylarsanium
SMILESC[As+](C)(C)CCO
InChI IdentifierInChI=1S/C5H14AsO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
InChI KeyORLOBEXOFQEWFQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oxygen-containing organoarsenic compounds. These are organoarsenic compounds that containing an oxygen atom.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentOxygen-containing organoarsenic compounds
Alternative Parents
Substituents
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceNo data.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5 g/LALOGPS
logP1.68ALOGPS
logP0.73ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)14.68ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.69 m³·mol⁻¹ChemAxon
Polarizability14.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-014i-0900000000-62a50030944c8480dfe2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-01b9-4920000000-0bf6eab86e3b6ca216feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-5ae4b33db69fe147bea7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-79c8c18c45f6969f5d03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-5900000000-dfa441521fa2da24b2bfView in MoNA
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6); dermal (6)
Mechanism of ToxicityArsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carginogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (3, 1)
MetabolismArsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (7)
Toxicity ValuesLD50: 6.5 g/kg (Oral, Rodent) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (10)
Uses/SourcesNo data.
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (9) Chronic Oral: 0.0003 mg/kg/day (9) Chronic Inhalation: 0.01 mg/m3 (9)
Health EffectsArsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, esepcially in skin, liver, bladder and lung cancers. (3, 7)
SymptomsExposure to lower levels of arsenic can cause nausea and vomiting, decreased production of red and white blood cells, abnormal heart rhythm, damage to blood vessels, and a sensation of burn (3).
TreatmentArsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Charcoal tablets may also be used for less severe cases. In addition, maintaining a diet high in sulfur helps eliminate arsenic from the body. (7)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032683
FooDB IDFDB010640
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID94618
ChEBI ID134092
PubChem Compound ID104820
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1580419
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16746711
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2363511
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=27277209
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2953397
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3288685
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3349210
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=3435795
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=6642710
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6719099
11.
12.
13. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.