ContaminantDB: Butyl cyanoacrylate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (39)XML

Record Information

Version

1.0

Creation Date

2009-06-22 16:08:27 UTC

Update Date

2026-04-14 18:44:16 UTC

Accession Number

CHEM001451

Identification

Common Name

Butyl cyanoacrylate

Class

Small Molecule

Description

Butyl cyanoacrylate is a chemical compound of cyanide. It is the main component of medical cyanoacrylate glues, which are used as adhesives for lacerations of the skin, and in the treatment of bleeding from vascular structures. (3)

Contaminant Sources

T3DB toxins

Contaminant Type

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

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Butyl 2-cyanoacrylate polymers	Kegg
Histoacryl	Kegg
Butyl 2-cyanoacrylic acid polymers	Generator
Enbucrilic acid	Generator
Butyl cyanoacrylic acid	Generator
Chirurcoll	MeSH
Cyanoacrylate, polybutyl	MeSH
Enbucrylate	MeSH
Ligament-fimomed	MeSH
N-Butyl-2-cyanoacrylate	MeSH
2 Cyanobutylacrylate	MeSH
Butyl 2 cyanacrylate	MeSH
Butylcyanoacrylate	MeSH
Enbucrilate	MeSH
Enbucrilate, homopolymer	MeSH
Fimomed	MeSH
Histacryl	MeSH
Kanokonlit	MeSH
NBCA compound	MeSH
Histoacryl blue	MeSH
2-Cyanobutylacrylate	MeSH
Butyl 2-cyanacrylate	MeSH
Homopolymer enbucrilate	MeSH
Histoacryl N-blau	MeSH
Braun brand OF enbucrilate	MeSH
N-Butyl-cyanoacrylate	MeSH
Polybutyl cyanoacrylate	MeSH
Butyl 2-cyanacrylates	MeSH
Cyanoacrylates, polybutyl	MeSH
Enbucrilates, homopolymer	MeSH
Histoacryl N blau	MeSH
Poly(isobutyl cyanoacrylate)	MeSH
Polyisobutyl cyanoacrylate	MeSH
Cyanoacrylate, polyisobutyl	MeSH
Enbucrilates	MeSH
N-Butyl-cyanoacrylates	MeSH
N-Butyl-2-cyanoacrylates	MeSH
Polyisobutylcyanoacrylate	MeSH
Cyanoacrylates, polyisobutyl	MeSH
Enbucrylates	MeSH
NBCA compounds	MeSH
Polyisobutylcyanoacrylates	MeSH
N Butyl 2 cyanoacrylate	MeSH
2-Cyanobutylacrylates	MeSH
Butylcyanoacrylates	MeSH
Histacryls	MeSH
Histoacryls	MeSH
N Butyl cyanoacrylate	MeSH
Polybutyl cyanoacrylates	MeSH
Polyisobutyl cyanoacrylates	MeSH

Chemical Formula

C₈H₁₁NO₂

Average Molecular Mass

153.178 g/mol

Monoisotopic Mass

153.079 g/mol

CAS Registry Number

6606-65-1

IUPAC Name

butyl 2-cyanoprop-2-enoate

Traditional Name

butyl cyanoacrylate

SMILES

CCCCOC(=O)C(=C)C#N

InChI Identifier

InChI=1S/C8H11NO2/c1-3-4-5-11-8(10)7(2)6-9/h2-5H2,1H3

InChI Key

JJJFUHOGVZWXNQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cyanoacrylates. These are organonitrogen compounds containing an acrylic acid ester, which carries a nitrile group. They have the general structure ROC(=O)C(=C)C#N, where R is an organic group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Cyanoacrylates

Alternative Parents

Substituents

Cyanoacrylic acid ester
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

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

Liquid

Appearance

Colorless liquid.

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	1.27 g/L	ALOGPS
logP	1.76	ALOGPS
logP	2.05	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	50.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.99 m³·mol⁻¹	ChemAxon
Polarizability	16.4 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	splash10-001i-9000000000-de89b24c0ed69a3b22c3	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	splash10-0udi-6900000000-ad22fa5afcedd1d434fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-9200000000-ade990bf211784733d89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-1074e0a0eb69e6af6c37	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-9206b3487be1b0c83a20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-9200000000-0c4adeabffe726c2e935	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-9000000000-b6af25e2c5a175a883ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uei-9200000000-1998dc145177e9e722b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9000000000-664865b47a0d1e5318a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-04aaa05a3fd8a1c8055a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-6900000000-af198457c4127b7be444	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-9100000000-a598a52ee9d376dd5324	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-9000000000-e9bd5508fc3e0d49e47f	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

211 to 300 milligrams for an adult human (cyanide salts). (4)

Carcinogenicity (IARC Classification)

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

Uses/Sources

Butyl cyanoacrylate is the main component of medical cyanoacrylate glues, which are used as adhesives for lacerations of the skin, and in the treatment of bleeding from vascular structures. (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

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

DB12358

HMDB ID

Not Available

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

Butyl cyanoacrylate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

23087

Kegg Compound ID

C13415

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Butyl cyanoacrylate (CHEM001451)

Structure for CHEM001451: Butyl cyanoacrylate