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Cinmethylin

HCID 91745
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
87818-31-3
Standard-SMILES
Cc1ccccc1CO[C@@H]1C[C@@]2(C(C)C)CC[C@]1(C)O2
InChIKey
QMTNOLKHSWIQBE-FGTMMUONSA-N
Summenformel
C18H26O2
Durchschnittliche Molmasse
274,4 g/mol
Monoisotopische Masse
274,19328007

Überblick

Exo-(+)-cinmethylin is a 1-methyl-2-[(2-methylbenzyl)oxy]-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane that is the exo-(+)-isomer of cinmethylin. It is an enantiomer of an exo-(-)-cinmethylin.

Namen und Bezeichner

Bevorzugter Name
Cinmethylin
IUPAC
(1S,2R,4R)-1-methyl-2-[(2-methylphenyl)methoxy]-4-propan-2-yl-7-oxabicyclo[2.2.1]heptane
Englischer Name
Cinmethylin
Summenformel
C18H26O2
Molmasse
274.4

Namen und Synonyme

CinmethylinArgoldCinch87818-31-3Cinmethylin [ISO]Caswell No. 731GDTXSID3034456EPA Pesticide Chemical Code 128837SD95481SD 95481ZV3871E43YCINMETHYLIN [MI]
Weitere Namen anzeigen
SKH 301WL 95481exo-(+-)-xy)(2.2.1)heptane
DTXCID60196478EC 402-410-9(+-)-exo-1-Methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-7-oxabicyclo(2.2.1)heptane7-Oxabicyclo(2.2.1)heptene exo-(+-)-1-methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-7-Oxabicyclo(2.2.1)heptane, 1-methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-, exo-(+-)-SD-95481(1S,2R,4R)-4-isopropyl-1-methyl-2-(o-tolylmethoxy)-7-oxabicyclo[2.2.1]heptane(1R,2S,4S)-rel-1-Methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicyclo[2.2.1]heptane

Datenbank-Bezeichner

CAS
87818-31-3
PubChem CID
91745
DTXSID
DTXSID3034456
ChEMBL
CHEMBL1903971、CHEMBL2229480
ChEBI
CHEBI:145563
UNII
ZV3871E43Y
EC Number

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,8
Polarare Oberfläche (TPSA)
18,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
4
Schwere Atome
20
Formalladung
0
Komplexität
353

Experimentelle und physikochemische Eigenschaften

Pesticides · 2 Einträge

Herbicides

Active substance -> EU Pesticides database: Pending

Collision Cross Section169.7 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3034456]

Physikochemische Eigenschaften

Schmelzpunkt
25 °C · 25°C
Siedepunkt
313 °C · 313°C
Dichte
20 · d20 1015 kg/m3
Brechungsindex
1.48 · 1.4800 (estimate)
Flammpunkt
147 °C · 147 °C
storage temp.
0 · 0-6°C
Henry's Law Constant
1.3 · 1.3×101 mol/(m3Pa) at 25℃, Ebert et al. (2023)
Major Application
agricultureenvironmental
InChI
1S/C18H26O2/c1-13(2)18-10-9-17(4,20-18)16(11-18)19-12-15-8-6-5-7-14(15)3/h5-8,13,16H,9-12H2,1-4H3/t16-,17+,18-/m1/s1

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

P261, P271, P273, P304+P340, P317, P391, and P501 (click each P-code to see the statement)

Warning

H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

P261, P271, P273, P304+P340, P317, P391, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory InformationREACH registered substance: Exo-(+/-)-1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicyclo[2.2.1]heptane (EC: 402-410-9)
Hazard Classes and Categories · 4 Einträge

Acute Tox. 4 (100%)

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute Tox. 4 *

Toxikologische Informationen

Treatment · 1 Eintrag

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

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

Verwendung und Herstellung

UsesThis is a man-made compound that is used as a pesticide.
Anwendungen · 2 Einträge

BeschreibungCinmethylinwas developed by Shell Chemical Company in the early 1980s as a weed control agent for monocotyledonous species. This herbicide controls important grasses such as green foxtail (Setaria viridis) and barnyardgrass (Echinochloa crus-galli) and suppresses the growth of several broadleaf weeds such as prickly sida (Sida spinosa) and velvetleaf (Abutilon theophrasti).

VerwendenCinmethylin is used as pre-emergence grass herbicide. Cinmethylin is member of the cineole eucalyptol family.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Tert-butyric acidNatriumacetatToluol-4-sulfonsureStickstoffCineolHept-1-in

Zugehörige Reaktionen

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Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
402-410-9、618-074-3
Nikkaji
J409.103E
InChIKey
QMTNOLKHSWIQBE-FGTMMUONSA-N
SMILES
CC(C)[C@]12CC[C@](C)(O1)[C@@H](C2)OCc3ccccc3C
CAS Datenbank
87818 · 87818-31-3(CAS DataBase Reference)
EPA chemische Informationen
Cinmethylin (87818-31-3)
· 1 Eintrag

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. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Toxicity Summary · 1 Eintrag

Cinmethylin is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. 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. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Signs and Symptoms · 1 Eintrag

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include 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. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

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

Sicherheitsdaten

wgk
3
ridadr
UN3082 9/PG 3
hs_code
29321900
RTECS-Nr.
RN8762000
risk_code
20-51/53
Toxizität
LD50 orally in rats: 4.5 g/kg; LD50 dermally in rabbits: >2 g/kg (Lee)
hazard_code
Xn,N
safety_code
23-61-22
Speicherklasse
10 - Combustible liquids
Hazard Classifications
Acute Tox. 4 InhalationAquatic Chronic 2
tert-Butylhydroperoxid
Terpin
[1,1,2,2-2H4]Ethan-1,2-[2H2]diol
Double ring
1,3-Diamino-propan
Glutarsure
Lithium

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