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Record Information
Version1.0
Creation Date2009-03-06 18:58:25 UTC
Update Date2016-11-09 01:08:11 UTC
Accession NumberCHEM000231
Identification
Common NameAdamsite
ClassSmall Molecule
DescriptionAdamsite is an organoarsenic compound which belongs to the group of chemical warfare agents known as vomiting agents or sneeze gases. Due to its toxicity, it is nowadays considered obsolete. Arsenic is a chemical element that has the symbol As and atomic number 33. It is a poisonous metalloid that has many allotropic forms: yellow (molecular non-metallic) and several black and grey forms (metalloids) are a few that are seen. Three metalloidal forms of arsenic with different crystal structures are found free in nature (the minerals arsenopyrite and the much rarer arsenolamprite and pararsenolamprite), but it is more commonly found as a compound with other elements. (6, 3)
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Amine
  • Arsenic Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
10-Chloro-5,10-dihydroarsacridineMeSH
Phenarsazine chlorideMeSH
DiphenylaminochloroarsineMeSH
Chemical FormulaC12H9AsClN
Average Molecular Mass277.581 g/mol
Monoisotopic Mass276.964 g/mol
CAS Registry Number578-94-9
IUPAC Name10-chloro-5,10-dihydrophenarsazinine
Traditional Nameadamsite
SMILESCl[As]1C2=CC=CC=C2NC2=CC=CC=C12
InChI IdentifierInChI=1S/C12H9AsClN/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8,15H
InChI KeyPBNSPNYJYOYWTA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzarsazines and derivatives. These are polycyclic aromatic compounds containing a benzene ring fused to a 1,4-azarsine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassMetalloheterocyclic compounds
Sub ClassBenzarsazines and derivatives
Direct ParentBenzarsazines and derivatives
Alternative Parents
Substituents
  • Benzarsazine skeleton
  • Benzenoid
  • Trivalent organic arsenic compound
  • Azacycle
  • Organic metalloid salt
  • Secondary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organonitrogen compound
  • Organoarsenic compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceYellow or green crystals.
Experimental Properties
PropertyValue
Melting Point195°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP3.88ALOGPS
logP3.54ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.83ChemAxon
pKa (Strongest Basic)0.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity59.51 m³·mol⁻¹ChemAxon
Polarizability24.07 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-f84914f36f818194452cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-52d6a51720bdcdf08113View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1090000000-112426d30b1483177755View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f020fab818516027081dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-067adeb9b616ebd30f83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-d84f7ad934008c089341View in MoNA
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5); dermal (5)
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. (2, 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: 35 mg/kg (Intravenous, Mouse) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (10)
Uses/SourcesAdamsite is used mainly as a riot control agent. (6)
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. (2, 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
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 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 LinkAdamsite
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID11362
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available