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Dimetan

HCID 31201
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Basic information

CAS
122-15-6
Standard SMILES
CN(C)C(=O)OC1=CC(=O)CC(C)(C)C1
InChIKey
ITEQSCBLCCNACE-UHFFFAOYSA-N
Molecular formula
C11H17NO3
Average molar mass
211.26 g/mol
Monoisotopic mass
211.1208434

Overview

Dimetan 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. (L795)

Names & identifiers

Preferred name
Dimetan
IUPAC
(5,5-dimethyl-3-oxocyclohexen-1-yl) N,N-dimethylcarbamate
English name
5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate
Molecular formula
C11H17NO3
Molecular weight
211.26

Names & synonyms

DIMETAN122-15-6Geigy 192585,5-Dimethyl-3-oxocyclohex-1-enyl dimethylcarbamateUNII-215ZV6RPXLEINECS 204-525-8215ZV6RPXL5,5-Dimethyl-3-oxo-1-cyclohexen-1-yl dimethylcarbamateENT 24,728BRN 3280184AI3-24728DIMETAN [MI]
Show more names
G-19258ENT-24738Geigy-19258Dimetan (Geigy)5,5-DIMETHYLDIHYDRORESORCINOL DIMETHYLCARBAMATE)N,N-Dimethylcarbamic acid 5,5-dimethyl-3-oxo-1-cyclohexen-1-ylN,N-Dimethylcarbamic acid 5,5-dimethyl-3-oxo-1-cyclohexen-1-yl esterCarbamic acid, N,N-dimethyl-, 5,5-dimethyl-3-oxo-1-cyclohexen-1-yl ester5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate 5,5-dimethyldihydroresorcinol dimethylcarbamate dimetan
5,5-Dimethyldihydroresorcinol dimethylcarbamateG 19258Dimethylcarbamate de 5,5-dimethyl dihydroresorcinol [French]DTXSID80418725,5-Dimethyl-dihydroresorcinol-N,N-dimethylcarbamat [German]2-Cyclohexen-1-one, 3-hydroxy-5,5-dimethyl-, dimethylcarbamate5,5-Dimethyl-4,5-dihydro-3-resorcyl-dimethyl-carbamat [German]GEIGY-19,258

Properties

Computed structural properties

XLogP
1.2
Topological polar surface area
46.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
15
Formal charge
0
Complexity
316

Physicochemical properties

Melting point
45 · 45-46°
Boiling point
11 · bp11 170-180°; bp0.3 122-124°
Density
1.124 · 1.1240 (rough estimate)
refractive index
1.5718 · 1.5718 (estimate)
pka
-1.33 · -1.33±0.70(Predicted)
Water Solubility
29.13 g/L · 29.13g/L(temperature not stated)
FDA UNII
215 ZV6RPXL · 215ZV6RPXL
EPA Substance Registry System
Dimetan (122-15-6)
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301
Precautionary statements
264 · P264-P270-P301+P310-P321-P330-P405-P501
Hazard Codes
T
Risk Statements
25 · 25
Safety Statements
36 · 36/37-45

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Hazard information

Hazard Classes and Categories · 2 items

Acute toxicity - category 3

Acute Tox. 3 *

Toxicology

Treatment · 1 item

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.

Health Effects · 1 item

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 (A15321).

Chemistry & industry

Pharmacology

Metabolism/MetabolitesThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Uses & manufacturing

UsesDimetan is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Applications

UsesInsecticide (aphicide).

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
122-15-6
PubChem CID
31201
DTXSID
DTXSID8041872
UNII
215ZV6RPXL
EC Number
204-525-8
Nikkaji
J5.350C
Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

Dimetan 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.

Signs and Symptoms · 1 item

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. (L795)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

risk_code
25
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T
safety_code
36/37-45
Hazard statements
H301
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501