ContaminantDB: Methyl isothiocyanate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (43)XML

Record Information

Version

1.0

Creation Date

2009-05-25 19:43:14 UTC

Update Date

2026-03-27 01:59:03 UTC

Accession Number

CHEM000699

Identification

Common Name

Methyl isothiocyanate

Class

Small Molecule

Description

Methyl isothiocyanate is found in horseradish. Methyl isothiocyanate is isolated from mustard oil, present as glucoside (Methyl glucosinolate LBB66-Y).

Contaminant Sources

Clean Air Act Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Cyanide Compound
Food Toxin
Industrial/Workplace Toxin
Metabolite
Organic Compound
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Methyl mustard	ChEBI
Methyl mustard oil	ChEBI
Methyl isothiocyanic acid	Generator
Methylisothiocyanate	MeSH
(methylimino)(thioxo)Methane	HMDB
(methylimino)thioxo-Methane	HMDB
Biomet 33	HMDB
isothiocyanato-Methane	HMDB
Isothiocyanatomethane	HMDB
Isothiocyanatomethane, 9ci	HMDB
Isothiocyanic acid, methyl ester	HMDB
Mencs	HMDB
Methane isothiocyanate	HMDB
Methyl thioisocyanate	HMDB
methylimino-Sulfanylidenemethane	HMDB
MIC	HMDB
MIT	HMDB
MITC	HMDB
Morton ep-161E	HMDB
MTC	HMDB
Trapex	HMDB
Trapex-40	HMDB
Trapexide	HMDB
Tropex	HMDB
Vorlex	HMDB
Vortex	HMDB

Chemical Formula

C₂H₃NS

Average Molecular Mass

73.117 g/mol

Monoisotopic Mass

72.999 g/mol

CAS Registry Number

556-61-6

IUPAC Name

isothiocyanatomethane

Traditional Name

methyl isothiocyanate

SMILES

CN=C=S

InChI Identifier

InChI=1S/C2H3NS/c1-3-2-4/h1H3

InChI Key

LGDSHSYDSCRFAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as isothiocyanates. These are organic compounds containing the isothiocyanate group, an isocyanate analogue with the general formula RN=C=S.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Isothiocyanates

Sub Class

Not Available

Direct Parent

Isothiocyanates

Alternative Parents

Substituents

Isothiocyanate
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

isothiocyanate (CHEBI:78337 )
Nematicides (C18587 )

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

fumigant

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless crystals.

Experimental Properties

Property	Value
Melting Point	36°C
Boiling Point	Not Available
Solubility	7.6 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	3.21 g/L	ALOGPS
logP	1.07	ALOGPS
logP	1.07	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	21.33 m³·mol⁻¹	ChemAxon
Polarizability	7.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9000000000-b429ebb7bc29e9080486	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9000000000-b429ebb7bc29e9080486	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9000000000-2527f314295b7bfab79f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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	splash10-00di-9000000000-41251e04c7de47748864	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-dd8d28c4ea09d9a33216	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-3618f39f822ca6449601	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-29d8e0d1e68982da1e8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-9e71c2e3c8188c76c9f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-5cec5e480b6d50aaaa27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-df2fb47319062974eb55	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-df2fb47319062974eb55	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-31fd3202304caf529d2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-b5edf8889f68e25b4f1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-b5edf8889f68e25b4f1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-b5edf8889f68e25b4f1b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9000000000-ac93c1d6593ab3603d13	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	13C 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	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	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	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	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (1) ; oral (1) ; dermal (1)

Mechanism of Toxicity

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

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes 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

LD50: 90-104 mg/kg (Oral, Mouse) (5) LD50: 54 mg/kg (Intraperitoneal, Rat) (4) LD50: 59 mg/kg (Subcutaneous, Rat) (4) LD50: 2780 mg/kg (Dermal, Rat) (4) LC50: 1900 mg/m3 over 1 hour (Inhalation, Rat) (4)

Lethal Dose

200 to 300 milligrams for an adult human (cyanide salts). (6)

Carcinogenicity (IARC Classification)

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

Uses/Sources

Methyl isothiocyanate is a precursor to a variety of valuable bioactive compounds and is also used in agriculture as a soil fumigant. (3)

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

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0034106

FooDB ID

FDB012372

Phenol Explorer ID

Not Available

KNApSAcK ID