ContaminantDB: 3-Iodo-2-propynyl butyl carbamate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (16)XML

Record Information

Version

1.0

Creation Date

2009-06-17 23:52:59 UTC

Update Date

2026-04-14 20:23:49 UTC

Accession Number

CHEM000767

Identification

Common Name

3-Iodo-2-propynyl butyl carbamate

Class

Small Molecule

Description

3-Iodo-2-propynyl butyl carbamate is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (3)

Contaminant Sources

Clean Air Act Chemicals
Cosmetic Chemicals
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Carbamate
Ester
Ether
Household Toxin
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Iodo-2-propyn-1-yl N-butylcarbamate	ChEBI
3-Iodoprop-2-ynyl butylcarbamate	ChEBI
Butyl-3-iodo-2-propynylcarbamate	ChEBI
Iodocarb	ChEBI
Iodocarbe	ChEBI
Iodopropynyl butylcarbamate	ChEBI
IPBC	ChEBI
Troysan KK-108a	ChEBI
Troysan polyphase anti-mildew	ChEBI
Woodlife	ChEBI
3-Iodo-2-propyn-1-yl N-butylcarbamic acid	Generator
3-Iodoprop-2-ynyl butylcarbamic acid	Generator
Butyl-3-iodo-2-propynylcarbamic acid	Generator
Iodopropynyl butylcarbamic acid	Generator
3-Iodo-2-propynyl butylcarbamic acid	Generator
3-Iodo-2-propynyl butyl carbamic acid	HMDB
3-IPBC	HMDB
3-Iodo-2-propynyl-butylcarbamate	HMDB
3-Iodo-2-propynylbutylcarbamate	HMDB
3-iodo-2-Propynyl butylcarbamate	ChEBI

Chemical Formula

C₈H₁₂INO₂

Average Molecular Mass

281.091 g/mol

Monoisotopic Mass

280.991 g/mol

CAS Registry Number

55406-53-6

IUPAC Name

3-iodoprop-2-yn-1-yl N-butylcarbamate

Traditional Name

iodopropynyl butylcarbamate

SMILES

CCCCNC(=O)OCC#CI

InChI Identifier

InChI=1S/C8H12INO2/c1-2-3-6-10-8(11)12-7-4-5-9/h2-3,6-7H2,1H3,(H,10,11)

InChI Key

WYVVKGNFXHOCQV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as carboximidic acids and derivatives. Carboximidic acids and derivatives are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Not Available

Direct Parent

Carboximidic acids and derivatives

Alternative Parents

Substituents

Haloacetylene or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organoiodide
Organohalogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carbamate ester (CHEBI:83279 )
organoiodine compound (CHEBI:83279 )
acetylenic compound (CHEBI:83279 )
carbamate fungicide (CHEBI:83279 )

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

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	66°C
Boiling Point	Not Available
Solubility	0.156 mg/mL at 20°C [JUERGENSEN,L et al. (2000)]

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	1.79	ALOGPS
logP	2.54	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	54.8 m³·mol⁻¹	ChemAxon
Polarizability	22.95 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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	splash10-08fr-8910000000-c2198b551efba8033141	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-03di-0900000000-b4d628d7dbd856cc520b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-03di-0900000000-e30fba30f8716fb5e9b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-06s9-0930000000-dc7530cdc80507d195e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-08g0-0920000000-ba057bb29bce4057c5a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-03di-1920000000-a0395470a4adb5de5c77	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-06s9-0930000000-8bd885f11b9544b3b25f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-03di-0900000000-5a59f90422bd99325496	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-03di-0900000000-357e5a9da968087b7ff6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-26ce5480f49bf180fed8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-03di-0900000000-4907115190dc317431e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-d2e28e17ee9d97baa699	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-03di-0900000000-8ba604109cfddf6a4311	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-03di-0900000000-932641616ba3ea78adb8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0930000000-431527f49af43b5a9238	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0900000000-83863c4f3fbb9266f126	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-03di-0900000000-c48f613fee6a7ea02ee1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-03di-0900000000-f81baee3a42d1c2be99a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-0e4ab8bd9f070a9bd117	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-06s9-0930000000-f85922bd3ab9109a6fc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0089-9570000000-0b591a043a5ababff9e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-9210000000-7563a4db509feaa37219	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-2bbe61eb999d8169ab91	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9130000000-053d97dcb301e23822a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-9120000000-75857c9eb9c5f50e1b71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9220000000-b2456c3774d6442aac9c	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (2) ; oral (2); dermal (2)

Mechanism of Toxicity

3-Iodo-2-propynyl butyl carbamate is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

Metabolism

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (2)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

3-Iodo-2-propynyl butyl carbamate is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Minimum Risk Level

Not Available

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (1).

Symptoms

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (3)

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0246958

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID