ContaminantDB: Methylene thiocyanate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (66)XML

Record Information

Version

1.0

Creation Date

2009-06-22 16:08:26 UTC

Update Date

2026-03-26 22:40:58 UTC

Accession Number

CHEM001432

Identification

Common Name

Methylene thiocyanate

Class

Small Molecule

Description

Methylene thiocyanate is a chemical compound of cyanide.

Contaminant Sources

STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Cyanide Compound
Ether
Household Toxin
Industrial/Workplace Toxin
Nitrile
Organic Compound
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
CH2(SCN)2	ChEBI
Dithiocyanatomethane	ChEBI
Methylene dithiocyanate	ChEBI
Methylenedirhodanid	ChEBI
Methylenedirhodanide	ChEBI
N-948 Biocide	ChEBI
Thiocyanic acid, C,c'-methylene ester	ChEBI
Thiocyanic acid, methylene ester	ChEBI
Methylene dithiocyanic acid	Generator
Thiocyanate, C,c'-methylene ester	Generator
Thiocyanate, methylene ester	Generator
Methylene thiocyanic acid	Generator
Methylene bis(thiocyanate)	MeSH

Chemical Formula

C₃H₂N₂S₂

Average Molecular Mass

130.191 g/mol

Monoisotopic Mass

129.966 g/mol

CAS Registry Number

6317-18-6

IUPAC Name

{[(cyanosulfanyl)methyl]sulfanyl}carbonitrile

Traditional Name

methylene bisthiocyanate

SMILES

N#CSCSC#N

InChI Identifier

InChI=1S/C3H2N2S2/c4-1-6-3-7-2-5/h3H2

InChI Key

JWZXKXIUSSIAMR-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dithioacetals. Dithioacetals are compounds containing a dithioacetal functional group with the general structure R2C(SR')2.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioacetals

Sub Class

Dithioacetals

Direct Parent

Dithioacetals

Alternative Parents

Substituents

Thioacetal
Sulfenyl compound
Thiocyanate
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Yellow solid.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.44 g/L	ALOGPS
logP	0.39	ALOGPS
logP	1.16	ChemAxon
logS	-1.4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	47.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	33.22 m³·mol⁻¹	ChemAxon
Polarizability	11.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9700000000-74f42ea0595be421e399	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-60d19c27d26cdb1c3ee3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-0900000000-9e41cbdcab631626f8a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-4900000000-41fd085775dfaa571324	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8b0071fe7a797cbdcf4f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1900000000-8e1219fdff9c7be95188	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-ee2e4592354a79b82721	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-d8809234fd836ceed007	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-d8809234fd836ceed007	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-e7d743502878a38df7df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-0e7b6ff1c9c56fbc506e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9100000000-121b6ded5805fdc1d81d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-286b63d3516de7d14a12	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dj-9000000000-26b07e3e0d9988fb3655	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (1) ; inhalation (1) ; dermal (1)

Mechanism of Toxicity

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. (2)

Metabolism

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. (1)

Toxicity Values

Not Available

Lethal Dose

200 to 300 milligrams for an adult human (cyanide salts). (3)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (1, 2)

Symptoms

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (1, 2)

Treatment

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (2)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0254635

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

21349

ChEBI ID

134614

PubChem Compound ID

22772

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12209192

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16608508

Methylene thiocyanate (CHEM001432)

Structure for CHEM001432: Methylene thiocyanate