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Pyrolan

HCID 6888
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Basic information

CAS
87-47-8
Standard SMILES
Cc1cc(OC(=O)N(C)C)n(-c2ccccc2)n1
InChIKey
GEDIWDLJKRKBFT-UHFFFAOYSA-N
Molecular formula
C13H15N3O2
Average molar mass
245.28 g/mol
Monoisotopic mass
245.11642673

Overview

Pyrolan is a crystalline solid. (NTP, 1992)

Names & identifiers

Preferred name
Pyrolan
IUPAC
(5-methyl-2-phenylpyrazol-3-yl) N,N-dimethylcarbamate
English name
Pyrolan.
Molecular formula
C13H15N3O2
Molecular weight
245.28

Names & synonyms

PYROLANPyralan87-47-8Geigy G-220083-Methyl-1-phenylpyrazol-5-yl dimethylcarbamateCaswell No. 574AOMS 20ENT 17,588G-220083-Methyl-1-phenylpyrazol-5-yl dimethyl carbamateG 22008Dimethyl 5-(3-methyl-1-phenylpyrazolyl) carbamate
Show more names
PyrolanRNSC404297NSC 404297(5-methyl-2-phenyl-pyrazol-3-yl) N,N-dimethylcarbamateN,N-Dimethylcarbamic acid 3-methyl-1-phenyl-1H-pyrazol-5-yl
1-Phenyl-3-methyl-5-pyrazolyl N,N-dimethyl carbamateDimethylcarbamic acid, 3-methyl-1-phenylpyrazol-5-yl esterCarbamic acid, dimethyl-, 3-methyl-1-phenylpyrazol-5-yl esterDimethylcarbamic acid 3-methyl-1-phenyl-1H-pyrazol-5-yl esterPyrazol-5-ol, 3-methyl-1-phenyl-, dimethyl carbamate (ester)868K72C292ENT-17588NSC-404297

Database identifiers

CAS
87-47-8
PubChem CID
6888
DTXSID
DTXSID6042361
ChEMBL
CHEMBL1610900
UNII
868K72C292
Nikkaji
J4.278A

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
47.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
18
Formal charge
0
Complexity
290

Experimental & physicochemical properties

SpringerMaterials PropertiesFusion temperature
SolubilitySoluble (NTP, 1992)
Boiling Point320 to 324 °F at 0.2 mmHg (NTP, 1992)
Melting Point122 °F (NTP, 1992)
Physical DescriptionPyrolan is a crystalline solid. (NTP, 1992)

Physicochemical properties

Melting point
50 ° · 50°
Boiling point
0.2 · bp0.2 160-162°
Density
1.1477 · 1.1477 (rough estimate)
refractive index
1.56 · 1.5600 (estimate)
Water Solubility
1.996 g/L · 1.996g/L(temperature not stated)
Stability
Stability Incompatible with strong oxidizing agents.
FDA UNII
868 K72C292 · 868K72C292

Safety & regulation

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

Hazard information

DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: This compound is a reversible CHOLINESTERASE INHIBITOR. When heated to decomposition it emits toxic fumes of nitrogen oxides. (NTP, 1992)
Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds
Reactivity AlertsExplosive
Reactivity Profile · 1 item

PYROLAN is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Air and Water ReactionsWater soluble.

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

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

UsesPyrolan is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
Applications · 3 items

UsesInsecticide.

UsesPyrolan is the derivative of 3-Methyl-1-phenyl-2-pyrazolin-5-one (E335000), which inhibits the disease activity in rheumatoid arthritis.

General DescriptionCrystalline solid.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
EPA Substance Registry System
Pyrolan (87-47-8)
RIDADR
2757 · 2757
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Toxicity
50 orally · LD50 orally in rats: 62 mg/kg (Schafer)
Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

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).

Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

Pyrolan 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

ridadr
2757
Toxicity
LD50 orally in rats: 62 mg/kg (Schafer)
hazard_class
6.1(b)
packing_group
III