Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:03 UTC
Update Date2014-12-24 20:21:05 UTC
Accession NumberT3D0089
Identification
Common NameThiocyanate
ClassSmall Molecule
DescriptionThiocyanates are a group of compounds formed from a combination of sulfur, carbon, and nitrogen. Thiocyanates are found in various foods and plants and are produced primarily from the reaction of free cyanide with sulfur. This reaction occurs in the environment (for example, in industrial waste streams that contain cyanide) and in the human body after cyanide ingestion. Thiocyanates are present in water primarily because of discharges from coal processing, extraction of gold and silver, and mining industries. Thiocyanate is the major product formed from cyanide that passes into the body as the body attempts to rid itself of cyanide. (8)
Compound Type
  • Cyanide Compound
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Nitrile
  • Organic Compound
  • Plant Toxin
  • Pollutant
Chemical Structure
Thumb
Synonyms
Synonym
Ammonium sulfocyanate
Nitridosulfanidocarbon
Nitrodithiocarbone(1-)
Nitrodothiocarbonate
Rhodanid
Rhodanide
SCN
Thiocyanate ion
Thiocyanic acid
Thiocyanid
Weedazol TL
Chemical FormulaCNS
Average Molecular Mass58.083 g/mol
Monoisotopic Mass57.976 g/mol
CAS Registry Number302-04-5
IUPAC Namecyanosulfanide
Traditional Namethiocyanate
SMILES[S-]C#N
InChI IdentifierInChI=1S/CHNS/c2-1-3/h3H/p-1
InChI KeyInChIKey=ZMZDMBWJUHKJPS-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as thiocyanates. These are salts or esters of thiocyanic acid, with the general formula RSC#N (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiocyanates
Sub ClassNot Available
Direct ParentThiocyanates
Alternative Parents
Substituents
  • Thiocyanate
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility41.5 g/LALOGPS
logP0.22ALOGPS
logP0.51ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)0.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.09 m³·mol⁻¹ChemAxon
Polarizability4.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9000000000-afccae6819a2082a3b0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9000000000-f7f42d61861dc8b47e0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-9000000000-d0c4694dff8128c82e83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-96a5deef504fc8cb3052View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-3714ea8b8485698022feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a4aa9bc6ab8c5ca45d18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-9000000000-3e068a4808fd5db992f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000000000-5b443ccd8993bc2f9325View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-626420c56c66b85a0f64View in MoNA
Toxicity Profile
Route of ExposureOral (8); inhalation (8) ; dermal (8)
Mechanism of ToxicityThiocyanate (sulphocyanate or SCN) is believed to be a goitrogenic compound. It is a competitive inhibitor of the human thyroid sodium/iodide symporter NIS. Thus, the adverse effects of thiocyanate overload are especially noticeable when iodine availability is low. Intake of goitrogenic substances causes an adaptive increase in T3‰ЫЄs binding to brain nuclear receptors and in the activity of type II 5'-deiodinase, which generates T3 from T4. This altered function and availability of T3 is detrimental to the developing brain. Thiocyanate is also known to modulate activity of mammalian peroxidases. For instance, eosinophil peroxidase has been implicated in promoting oxidative tissue damage in a variety of inflammatory conditions, including asthma. Thiocyanate also acts as inhibitor to carbonic anhydrase, which catalyzes the rapid conversion of carbon dioxide to bicarbonate and protons. (1, 4, 6) Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (14)
MetabolismThiocyanates can appear in the body after metabolization of cyanides by rhodanese. When thiocyanates enter the body, they normally breaks down in aqueous solution to yield sulfate ions. However, thiocyanates are also found in the thyroid fluids. Immediately following exposure to thiocyanate containing solutions, the cystic fibrosis conductance regulator Cl‰ЫТ channel exhibits high unitary SCN‰ЫТ conductance and anomalous mole fraction behaviour. Thiocyanates is normally excreted in urine. (2, 3, 4, 5) Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (13)
Toxicity ValuesGuanidine Thiocyanate: LD50: 375 mg/kg (Oral, Rat), LD50: 2000 mg/kg (Dermal, Rabbit) (10) Potassium Thiocyanate: LD50: 854 mg/kg (Oral, Rat) (11) Ammonium Thiocyanate: LD50: 750 mg/kg (Oral, Rat), LD50: 500 mg/kg (Oral, Mouse) (12)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesExposure occurs from breathing air and drinking water, touching soil or water containing thiocyanate, or eating foods that contain thiocyanate. Thiocyanates are present in water primarily because of discharges from coal processing, extraction of gold and silver, and mining industries. Thiocyanate is the major product formed from cyanide that passes into the body as the body attempts to rid itself of cyanide, thus exposure to cyanide also results in exposure to thiocyanate. (8)
Minimum Risk LevelNot Available
Health EffectsThiocyanates are known to affect the thyroid glands, reducing the ability of the gland to produce hormones that are necessary for the normal function of the body. Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma and death. (8)
SymptomsSymptoms of thiocyanate exposure include rapid, deep breathing and shortness of breath, followed by convulsions (seizures) and loss of consciousness. (8)
TreatmentIn cases of thiocyanate exposure, get fresh air and medical attention. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. If swallowed, do not induce vomiting but give large quantities of water. Immediately flush skin with plenty of water for at least 15 minutes in case of exposure to skin or the eyes. (9)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB01453
PubChem Compound ID781
ChEMBL IDNot Available
ChemSpider ID8961
KEGG IDC01755
UniProt IDNot Available
OMIM ID
ChEBI ID18022
BioCyc IDHSCN
CTD IDNot Available
Stitch IDThiocyanate
PDB IDSCN
ACToR IDNot Available
Wikipedia LinkThiocyanate
References
Synthesis ReferenceLang, Konrad. Thiocyanate formation in the animal body. II. Biochemische Zeitschrift (1933), 263 262-7.
MSDSLink
General References
  1. van Dalen CJ, Kettle AJ: Substrates and products of eosinophil peroxidase. Biochem J. 2001 Aug 15;358(Pt 1):233-9. [11485572 ]
  2. Laurberg P, Nohr SB, Pedersen KM, Fuglsang E: Iodine nutrition in breast-fed infants is impaired by maternal smoking. J Clin Endocrinol Metab. 2004 Jan;89(1):181-7. [14715847 ]
  3. WOOD JL, WILLIAMS EF Jr: The metabolism of thiocyanate in the rat and its inhibition by propylthiouracil. J Biol Chem. 1949 Jan;177(1):59-67. [18107406 ]
  4. Taga I, Oumbe VA, Johns R, Zaidi MA, Yonkeu JN, Altosaar I: Youth of west-Cameroon are at high risk of developing IDD due to low dietary iodine and high dietary thiocyanate. Afr Health Sci. 2008 Sep;8(3):180-5. [19357747 ]
  5. Fragoso MA, Fernandez V, Forteza R, Randell SH, Salathe M, Conner GE: Transcellular thiocyanate transport by human airway epithelia. J Physiol. 2004 Nov 15;561(Pt 1):183-94. Epub 2004 Sep 2. [15345749 ]
  6. Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
  7. Paul BD, Smith ML: Cyanide and thiocyanate in human saliva by gas chromatography-mass spectrometry. J Anal Toxicol. 2006 Oct;30(8):511-5. [17132244 ]
  8. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for thiocyanate. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  9. Shanxi Friends Union Chemicals Co., Ltd. (2009). [Link]
  10. Promega (2006). Material Safety Data Sheet for Guanidine thiocynate. [Link]
  11. Flinn Scientific Inc. (2002).Material Safety Data Sheet for Potassium thiocyanate. [Link]
  12. ScienceLab.com (2009). Material Safety Data Sheet (MSDS) for Ammonium thiocyanate. [Link]
  13. ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  14. Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Sodium:iodide symporter activity
Specific Function:
Mediates iodide uptake in the thyroid gland.
Gene Name:
SLC5A5
Uniprot ID:
Q92911
Molecular Weight:
68665.63 Da
References
  1. Laurberg P, Nohr SB, Pedersen KM, Fuglsang E: Iodine nutrition in breast-fed infants is impaired by maternal smoking. J Clin Endocrinol Metab. 2004 Jan;89(1):181-7. [14715847 ]
  2. Taga I, Oumbe VA, Johns R, Zaidi MA, Yonkeu JN, Altosaar I: Youth of west-Cameroon are at high risk of developing IDD due to low dietary iodine and high dietary thiocyanate. Afr Health Sci. 2008 Sep;8(3):180-5. [19357747 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular Weight:
28870.0 Da
References
  1. Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
General Function:
Zinc ion binding
Specific Function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular Weight:
29245.895 Da
References
  1. Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA3
Uniprot ID:
P07451
Molecular Weight:
29557.215 Da
References
  1. Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular Weight:
35032.075 Da
References
  1. Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
General Function:
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 Da
References
  1. van Dalen CJ, Kettle AJ: Substrates and products of eosinophil peroxidase. Biochem J. 2001 Aug 15;358(Pt 1):233-9. [11485572 ]
General Function:
Thiocyanate peroxidase activity
Specific Function:
Antimicrobial agent which utilizes hydrogen peroxide and thiocyanate (SCN) to generate the antimicrobial substance hypothiocyanous acid (HOSCN) (By similarity). May contribute to airway host defense against infection.
Gene Name:
LPO
Uniprot ID:
P22079
Molecular Weight:
80287.055 Da
References
  1. Sheikh IA, Singh AK, Singh N, Sinha M, Singh SB, Bhushan A, Kaur P, Srinivasan A, Sharma S, Singh TP: Structural evidence of substrate specificity in mammalian peroxidases: structure of the thiocyanate complex with lactoperoxidase and its interactions at 2.4 A resolution. J Biol Chem. 2009 May 29;284(22):14849-56. doi: 10.1074/jbc.M807644200. Epub 2009 Apr 1. [19339248 ]
General Function:
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 Da
References
  1. van Dalen CJ, Whitehouse MW, Winterbourn CC, Kettle AJ: Thiocyanate and chloride as competing substrates for myeloperoxidase. Biochem J. 1997 Oct 15;327 ( Pt 2):487-92. [9359420 ]