Record Information
Version1.0
Creation Date2009-06-19 21:58:40 UTC
Update Date2026-04-05 17:37:15 UTC
Accession NumberCHEM001180
Identification
Common NameMersalyl acid
ClassSmall Molecule
DescriptionMersalyl acid is an organomercuric compound. It is used as a diuretic. Mercury is a heavy, silvery d-block metal and one of six elements that are liquid at or near room temperature and pressure. It is a naturally occuring substance, and combines with other elements such as chlorine, sulfur, or oxygen to form inorganic mercury compounds (salts). Mercury also combines with carbon to make organic mercury compounds. (6, 12)
Contaminant Sources
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Aromatic Hydrocarbon
  • Drug
  • Ester
  • Ether
  • Mercury Compound
  • Organic Compound
  • Organometallic
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC12H14HgNNaO7
Average Molecular Mass507.820 g/mol
Monoisotopic Mass509.037 g/mol
CAS Registry Number486-67-9
IUPAC Namesodium 2-[2-({2-[(hydroxymercurio)oxy]-2-methoxyethyl}carbamoyl)phenoxy]acetate
Traditional Namesodium 2-[2-({2-[(hydroxymercurio)oxy]-2-methoxyethyl}carbamoyl)phenoxy]acetate
SMILESCOC(CNC(=O)C1=CC=CC=C1OCC(=O)O[Na])O[Hg]O
InChI IdentifierInChI=1S/C12H14NO6.Hg.Na.H2O/c1-18-11(16)6-13-12(17)8-4-2-3-5-9(8)19-7-10(14)15;;;/h2-5,11H,6-7H2,1H3,(H,13,17)(H,14,15);;;1H2/q-1;+2;+1;/p-2
InChI KeyCGFDLNWSBILLGP-UHFFFAOYSA-L
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentPhenoxyacetic acid derivatives
Alternative Parents
Substituents
  • Phenoxyacetate
  • Benzoic acid or derivatives
  • Benzamide
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Secondary carboxylic acid amide
  • Carboxylic acid salt
  • Carboxamide group
  • Organic alkali metal salt
  • Organic metal salt
  • Organic transition metal salt
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.7 g/LALOGPS
logP-0.2ALOGPS
logP-0.5ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)14.04ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.32 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity65.08 m³·mol⁻¹ChemAxon
Polarizability31.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1070590000-41b6b3941686d7a0178cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ikc-1091530000-e8b60fbe8bccfd698cdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f8a-9520000000-f965a9e42f3104c56c4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0070290000-78c3c75a845f28504f75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0l6u-3469520000-0ba5134ecdf6f0a9366dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9436100000-c3805c5eae74259b21feSpectrum
Toxicity Profile
Route of ExposureOral (8) ; inhalation (8) ; dermal (8)
Mechanism of ToxicityHigh-affinity binding of the divalent mercuric ion to thiol or sulfhydryl groups of proteins is believed to be the major mechanism for the activity of mercury. Through alterations in intracellular thiol status, mercury can promote oxidative stress, lipid peroxidation, mitochondrial dysfunction, and changes in heme metabolism. Mercury is known to bind to microsomal and mitochondrial enzymes, resulting in cell injury and death. For example, mercury is known to inhibit aquaporins, halting water flow across the cell membrane. It also inhibits the protein LCK, which causes decreased T-cell signalling and immune system depression. Mercury is also believed to inhibit neuronal excitability by acting on the postsynaptic neuronal membrane. It also affects the nervous system by inhibiting protein kinase C and alkaline phosphatase, which impairs brain microvascular formation and function, as well as alters the blood-brain barrier. Organic mercury exerts developmental effects by binding to tubulin, preventing microtubule assembly and causing mitotic inhibition. Mercury also produces an autoimmune response, likely by modification of major histocompatibility complex (MHC) class II molecules, self peptides, T-cell receptors, or cell-surface adhesion molecules. (8, 3, 4, 5)
MetabolismOrganic mercury is absorbed mainly by the gastrointestinal tract, then distributed throughout the body via the bloodstream. Organic mercury complexes with free cysteine and the cysteine and sulfhydryl groups on proteins such as haemoglobin. These complexes are able to mimic methionine and thus be transported throughout the body, including through the blood-brain barrier and placenta. Organic mercury is metabolized into inorganic mercury, which is eventually excreted in the urine and faeces. (13)
Toxicity ValuesNot Available
Lethal Dose100 mg for an adult human (average for organic mercurials). (14)
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (11)
Uses/SourcesMersalyl acid is used as a diuretic. (12)
Minimum Risk LevelChronic Inhalation: 0.0002 mg/m3 (10)
Health EffectsMercury mainly affects the nervous system. Exposure to high levels of metallic, inorganic, or organic mercury can permanently damage the brain, kidneys, and developing fetus. Effects on brain functioning may result in irritability, shyness, tremors, changes in vision or hearing, and memory problems. Acrodynia, a type of mercury poisoning in children, is characterized by pain and pink discoloration of the hands and feet. Mercury poisoning can also cause Hunter-Russell syndrome and Minamata disease. (8)
SymptomsCommon symptoms include peripheral neuropathy (presenting as paresthesia or itching, burning or pain), skin discoloration (pink cheeks, fingertips and toes), edema (swelling), and desquamation (dead skin peels off in layers). (1)
TreatmentMercury poisoning is treated by immediate decontamination and chelation therapy using DMSA, DMPS, DPCN, or dimercaprol. (2)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMersalyl
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available