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3a,4,7,7a-テトラヒドロ-5-(ヒドロキシフェニル-2-ピリジニルメチル)-8-(フェニル-2-ピリジニルメチレン)-4,7-メタノ-1H-イソインドール-1,3(2H)-ジオン

Norbormide

HCID 13814
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
991-42-4
標準SMILES
O=C1NC(=O)C2C3C(C(O)(c4ccccc4)c4ccccn4)=CC(C3=C(c3ccccc3)c3ccccn3)C12
InChIKey
DNTHHIVFNQZZRD-UHFFFAOYSA-N
分子式
C33H25N3O3
平均分子量
511.6 g/mol
単同位体質量
511.18959167

概要

Norbormide is a colorless to off-white crystalline powder. Used as a selective rat poison. (EPA, 1998)

名称と識別子

優先名称
Norbormide
IUPAC
8-(hydroxy-phenyl-pyridin-2-ylmethyl)-10-[phenyl(pyridin-2-yl)methylidene]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
現地名
3a,4,7,7a-テトラヒドロ-5-(ヒドロキシフェニル-2-ピリジニルメチル)-8-(フェニル-2-ピリジニルメチレン)-4,7-メタノ-1H-イソインドール-1,3(2H)-ジオン
英語名
NORBORMIDE
分子式
C33H25N3O3
分子量
511.57

名称と別名

NORBORMIDERaticateShoxinNobormideMcneil 1025991-42-4Compound S-6,999MCN 1025S 6999ENT 51,762S-6,999K4085589CZ
名称をさらに表示
ノルボルマイド化合物S-6999ラチカート3a,4,7,7a-テトラヒドロ-5-(ヒドロキシフェニル-2-ピリジニルメチル)-8-(フェニル-2-ピリジニルメチレン)-4,7-メタノ-1H-イソインドール-1,3(2H)-ジオン3-[α-ヒドロキシ-α-(2-ピリジル)ベンジル]-7-[α-(2-ピリジル)ベンジリデン]ビシクロ[2.2.1]ヘプタ-2-エン-5,6-ジカルボキシミドショキシンノルボルミド8-[ヒドロキシ(フェニル)(ピリジン-2-イル)メチル]-10-[フェニル(ピリジン-2-イル)メチリデン]-4-アザトリシクロ[5.2.1.02,6]デカ-8-エン-3,5-ジオンs6999mcn1025raticideent51,762mcneil1025
4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-5-(hydroxyphenyl-2-pyridinylmethyl)-8-(phenyl-2-pyridinylmethylene)-DTXSID8042216NSC-1013165-Norbornene-2,3-dicarboximide, 5-(alpha-hydroxy-alpha-2-pyridylbenzyl)-7-(alpha-2-pyridylbenzylidene)-5-(alpha-Hydroxy-alpha-2-pyridylbenzyl)-7-(alpha-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximideRefChem:854698DTXCID00809772213-589-6

物性

構造計算による物性

XLogP
3.1
極性表面積
92.2 Ų
水素結合供与体数
2
水素結合受容体数
5
回転可能結合数
5
重原子数
39
形式電荷
0
複雑度
1,040

実験および物理化学的性質

PesticidesPesticides -> Rodenticides
Color/Form · 4 件

CRYSTALS FROM METHYLENE CHLORIDE + ETHER

COLORLESS TO OFF-WHITE CRYSTALLINE POWDER

White solid

White crystals

Solubility · 5 件

PRACTICALLY INSOL IN WATER UNLESS PH IS BELOW 4

SOLUBILITY @ ROOM TEMP: 60 MG/L WATER: @ 30 °C: 14 MG/L ETHANOL, GREATER THAN 150 MG/L CHLOROFORM, 1 MG/L DIETHYL ETHER, 29 MG/L 0.1 MOLAR HYDROCHLORIC ACID

Soluble in dilute acids.

In ethanol, 14 mg/l; >150 mg/l in chloroform; 1 mg/l in diethyl ether; 29 mg/l in 0.1 M hydrochloric acid (all at 30 °C).

In water 60 mg/l at 20 °C.

CorrosivityNon-corrosive
DecompositionWHEN HEATED TO DECOMPOSITION IT EMITS TOXIC FUMES OF NOx.
Melting Point · 2 件

374 to 388 °F (EPA, 1998)

190-198 °C

Physical Description · 2 件

Norbormide is a colorless to off-white crystalline powder. Used as a selective rat poison. (EPA, 1998)

Colorless, off-white, or white solid; [HSDB]

Stability/Shelf LifeIT IS...STABLE @ ROOM TEMP WHEN DRY, AND TO BOILING WATER; HYDROLYZED BY ALKALI.

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory InformationThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT LabelPoison
Fire HazardsWhen heated to decomposition, it emits toxic fumes of nitrogen oxides. Avoid alkalies. (EPA, 1998)
Health HazardsModerately to highly toxic to humans. Probable human lethal dose is 50 to 500 mg/kg, or 1 teaspoon to 1 pint for a 150 lb. person. (EPA, 1998)
Hazards Summary · 1 件

Causes convulsions in animal experiments; [HSDB] Selectively toxic to rats; Human exposures of up to 300 mg produced symptoms including slight decreases in systolic blood pressure and body temperature; [CAMEO] Effects in high-dose animal studies include cardiac arrhythmias, respiratory depression, and ataxia; [RTECS]

Reactive GroupAlcohols and Polyols
Reactivity ProfileWhen heated to decomposition, NORBORMIDE emits toxic fumes of nitrogen oxides. Avoid alkalis. [EPA, 1998].
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.

化学と産業

薬理情報

Mechanism of Action · 1 件

Species differences in response of the peripheral blood vessels to norbormide seemed to account for most of the observed species differences in its toxicity. The compound caused an extreme, irreversible vasoconstriction in laboratory rats, and this was considered the cause of death. ... An oral or ip dosage of 1,020 mg/kg caused a doubling of blood glucose levels and a decr of liver and muscle glycogen when coma began 0.5-2 hr after treatment. The same dosage had no effect on the glucose levels of two strains of mice, nor did it produce illness. Insulin counteracted the hyperglycemic effect of norbormide in rats but did not protect against toxic manifestations and death, suggesting that the hyperglycemia is secondary ... .

MeSH Pharmacological ClassificationSubstances used to destroy or inhibit the action of rats, mice, or other rodents.

用途と製造

Uses · 3 件

Used as selective rodenticide for control of rat (Rattus) species; [HSDB]

Farming (Pesticides) [Category: Industry]

Specific rodenticidal control of rat (Rattus) species.

Methods of Manufacturing...BY CONDENSATION OF 2-BENZOYLPYRIDINE & CYCLOPENTADIENE FOLLOWED BY REACTION OF THE OBTAINED FULVENE WITH MALEIMIDE.
Formulations/Preparations · 3 件

'RATICATE', CONCENTRATE (5-10 G AI/KG) FOR BAIT PREPN IN CEREAL OFFALS, FISH MEAL, ETC.

CONTAINED FORMERLY IN THE PREPARATION RATICATE...

Bait concentrate

General Manufacturing Information · 2 件

NORBORMIDE HAS VERY POOR BAIT ACCEPTANCE.

THIS DICARBOXIMIDE IS GENERALLY USED IN DRY BAITS AGAINST NORWAY (BROWN OR COMMON) RATS. IT IS FAST-ACTING & KILLS AFTER A SINGLE FEEDING.

応用分野 · 3 件

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
991-42-4
PubChem CID
13814
DTXSID
DTXSID8042216
ChEMBL
CHEMBL388119
ChEBI
CHEBI:82259
UNII
K4085589CZ
EC Number
213-589-6
Other Experimental Properties · 2 件

A MIXTURE OF STEREOISOMERS

Hydrolyzed by alkalis.

物理化学的性質

融点
190 · 190-198°
沸点
598.31 °C · 598.31°C (rough estimate)
比重(密度)
1.2065 · 1.2065 (rough estimate)
屈折率
1.78 · 1.7800 (estimate)
貯蔵温度
-20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
溶解性
クロロホルム(微量)、メタノール(微量、加温)
外見
個体
酸解離定数(Pka)
11.042 · 11.042±0.40(predicted)
色
クリスタル
水溶解度
60 mg/L · 60mg/L(室温)
Henry's Law Constant
3.7 · 3.7×1017 mol/(m3Pa) at 25℃, HSDB (2015)
安定性
光に敏感
EPAの化学物質情報
Norbormide (991-42-4)

化学的性質

化学的特性White solid. Insoluble in water; soluble in dilute acids.

CERCLA Reportable Quantities · 1 件

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Norbormide is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100/10,000 lbs.

Hazard Classes and Categories · 3 件

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute Tox. 4 *

安全と保護具

Fire Fighting · 1 件

(Non-Specific -- Pesticide, Solid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing.

First AidNote: Poisoning by norbormide is unlikely due to its low toxicity in humans (selectively toxic to rats).
Nonfire Spill Response(Non-Specific -- Pesticide, Solid, n.o.s.) Do not touch spilled material; stop leak if you can do so without risk.
Disposal Methods · 2 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Landfill: Recommendable method: Incineration. Peer-review: Large amt: Incinerate in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Protective Action Criteria (PAC) · 3 件

0.35 [mg/m3]

3.8 [mg/m3]

190 [mg/m3]

Personal Protective Equipment (PPE) · 1 件

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

毒性情報

Ecotoxicity Values · 2 件

LD50 MALLARD DUCKS ORAL GREATER THAN 3000 MG/KG, 9-10 MO OLD MALES

LD50 prairie dogs oral greater than 1000 mg/kg

Environmental Fate · 4 件

IT IS EXTREMELY STABLE & PERSISTENT IN ALL BAITS & ENVIRONMENTS.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2000(SRC), determined from an estimated log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that norbormide is expected to have slight mobility in soil(SRC). Volatilization of norbormide from moist soil surfaces is not expected (SRC) given an estimated Henry's Law constant of 2.7X10-23 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Norbormide is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 4.3X10-22 mm Hg(SRC), determined from a fragment constant method(5).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2000(SRC), determined from an estimated log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that norbormide is expected to adsorb to suspended solids and sediment in water(SRC). Norbormide is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.7X10-23 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 290(3,SRC), from an estimated log Kow(2,SRC), suggests that bioconcentration in aquatic organisms is high(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), norbormide, which has an estimated vapor pressure of 4.3X10-22 mm Hg at 25 °C(2,SRC), is expected to exist entirely in the particulate phase in the ambient atmosphere. Vapor-phase norbormide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 1.7 hours(3,SRC). Particulate-phase norbormide may be physically removed from the air by wet and dry deposition(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Soil Adsorption/Mobility · 1 件

The Koc of norbormide is estimated as approximately 2000(SRC), using an estimated log Kow of 3.5(1,SRC) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that norbormide is expected to have slight mobility in soil(SRC).

Human Toxicity Excerpts · 4 件

THREE ADULT MALE VOLUNTEERS RECEIVED 15 MG/KG DAILY FOR 3 DAYS WITHOUT ILL-EFFECT.

HUMANS INGESTING DOSES UP TO 300 MG SHOWED SLIGHT TRANSIENT DECR IN BODY TEMP & BLOOD PRESSURE. INTRADERMAL INJECTIONS (0.1 ML OF 0.1% SOLN) PRODUCED NO SKIN REACTIONS OR LESIONS IN MAN.

A case of contact dermatitis is described on a woman who poured over pesticide solution in order to make poisonous pesticides for rodents. The solution got on the skin of her hands, right crus and left forearm. There the signs of acute skin inflammation appeared along with the clinical picture of chronic dermatosis caused by the solution irritating characteristics.

... administered norbormide to volunteers po at doses ranging from 20 to 300 mg. No sign or symptom was produced. It was concluded that body temp and blood pressure decr slightly and temporarily following the larger doses. Actually, the largest fall in temp observed at any dose was 0.7 °C, and this occurred after doses of 20 and 80 mg, whereas the largest fall after a dose of 120 mg or more was only 0.3 °C. Systolic (but not diastolic) blood pressure possibly fell after 120 mg of norbormide and certainly fell after larger doses. The largest decr recorded were from 132/76 to 100/74 after 200 mg and from 120/80 to 96/80 after 300 mg. The lowest values were measured 1 hr after ingestion, and the values were essentially normal at 2 hr in each instance.

Artificial Pollution SourcesNorbormide's use as a rodenticide for the control of rat (Rattus) species(1) will result in its release to the environment(SRC).
Environmental Bioconcentration · 1 件

An estimated BCF value of 290 was calculated for norbormide(SRC), using an estimated log Kow of 3.5(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is high(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for norbormide is estimated as 2.7X10-23 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that norbormide will be essentially nonvolatile from water surfaces(2,SRC). Norbormide's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is not expected (SRC). Norbormide is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 4.3X10-22 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5 件

A SINGLE ORAL DOSE OF 1000 MG/KG HAD NO EFFECT ON...MONKEYS.../OR/ TURKEYS; NOR WAS IT LETHAL TO ANY OF 40 OTHER ANIMAL SPECIES TESTED.

REGURGITATION, DYSPNEA, POLYDIPSIA, SLIGHT LOSS OF BALANCE, EXCESSIVE PREENING. NO SIGNIFICANT CHANGES IN BODY WT...BY END OF 14-DAY OBSERVATION PERIOD. /MALLARD MALES 9-10 MO OLD, ACUTE ORAL STUDY/

...ACTS DIRECTLY ON SMOOTH MUSCLE OF PERIPHERAL VESSELS CAUSING THEM TO CONSTRICT IRREVERSIBLY RESULTING IN WIDESPREAD ISCHEMIA...DEATH. RECEPTOR SITES...DIFFERENT FROM.../THOSE/ FOR EPINEPHRINE. ...ASSUMED THAT NORBORMIDE RECEPTORS IN SMOOTH MUSCLE OF PERIPHERAL VESSELS EXIST UNIQUELY IN THE RAT...

IN RAT LIVER MITOCHONDRIA, MG2+-ACTIVATED ATPASE ACTIVITY WAS ENHANCED BY NORBORMIDE IN VITRO (4X10-4 MOLAR) OR IN VIVO (SINGLE ORAL DOSE OF 10 MG/KG). CA2+-ACTIVATED ATPASE WAS NOT AFFECTED. NONE OF THE ATPASES WERE AFFECTED IN MICE, FOLLOWING ORAL ADMINISTRATION OF 170 MG/KG. NORBORMIDE FEEDING HAD NO EFFECT ON THE TOTAL AND OUABAIN-SENSITIVE (NA+ + K+)-ATPASE ACTIVITIES IN THE ERYTHROCYTE MEMBRANE AND HEART MICROSOMES IN RATS. THE INCORPORATION OF INORGANIC (32)PHOSPHORUS INTO ATP, IN LIVER MITOCHONDRIA, WAS DECREASED BY NORBORMIDE BOTH IN VITRO AND IN VIVO. NORBORMIDE INHIBITED THE (45)CALCIUM UPTAKE BY LIVER MITOCHONDRIA AS WELL AS MITOCHONDRIAL SUCCINATE DEHYDROGENASE ACTIVITIES.

For more Non-Human Toxicity Excerpts (Complete) data for NORBORMIDE (13 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of norbormide with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Norbormide is not expected to undergo hydrolysis in the environment due to the lack of functional groups to hydrolyze(2,SRC).

Probable Routes of Human ExposureOccupational exposure to norbormide may occur through inhalation of dust particles and dermal contact with this rodenticide during its use or at workplaces where norbormide is produced. (SRC)
Environmental Fate/Exposure Summary · 1 件

Norbormide's former use as a rodenticide may have resulted in its release to the environment. If released to the atmosphere, norbormide is expected to exist entirely in the particulate phase in the ambient atmosphere based on an estimated vapor pressure of 4.3X10-22 mm Hg at 25 °C. Particulate-phase norbormide may be physically removed from the atmosphere by wet or dry deposition. If released to soil, norbormide is expected to have slight mobility based on an estimated Koc of 2000. Volatilization from wet and dry soil surfaces is not expected to occur based on an estimated Henry's Law constant of 2.7X10-23 atm-cu m/mole and the estimated vapor pressure for this compound, respectively. If released into water, norbormide is expected to adsorb to suspended solids and sediments in water based on its estimated Koc. An estimated BCF of 290 suggests that bioconcentration of norbormide in aquatic organisms is expected to occur. Norbormide is not expected to volatilize from water surfaces based on the Henry's Law constant for this compound. Occupational exposure to norbormide may have occurred through inhalation of dust particles and dermal contact with this rodenticide during its use or at workplaces where norbormide was produced. (SRC)

法規制情報

CERCLA Reportable Quantities · 1 件

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Norbormide is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100/10,000 lbs.

安全データ

ridadr
2588
毒性
LD50 in rats (mg/kg): 5.3 orally; 0.65 i.v. (Roszkowski)
risk_code
22
hazard_code
Xn
hazard_class
6.1(a)
packing_group
I
有毒物質データの
991-42-4(Hazardous Substances Data)
危険度評価(NFPA 704基準/消防庁データ)
人的[青]=4

説明Norbormide was first introduced on the market in 1964 as a selective raticide, but does not have a current registration for commercial use in the European Union or North America. Current use as a pesticide is minimal to nonexistent worldwide. This compound’s toxicity is highly specific for rats.

使用Norbormide is used as a rodenticide. It acts as a vasoconstrictor and calcium channel blocker, but is selectively toxic to rats and has relatively low toxicity to other species, due to a species specific action of opening the permeability transition pores in rat mitochondria.

一般的な説明Colorless to off-white crystalline powder. Used as a selective rat poison.

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補足説明

定義A rodenticide specific for rats, supposedly nontoxic to other animals or to humans .