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Norbormide

Norbormide structure

Norbormide 

structure
  • CAS No:

    991-42-4

  • Formula:

    C33H25N3O3

  • Chemical Name:

    Norbormide

  • Synonyms:

    4,7-Methano-1H-isoindole-1,3(2H)-dione,3a,4,7,7a-tetrahydro-5-(hydroxyphenyl-2-pyridinylmethyl)-8-(phenyl-2-pyridinylmethylene)-;5-Norbornene-2,3-dicarboximide,5-(α-hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-;3a,4,7,7a-Tetrahydro-5-(hydroxyphenyl-2-pyridinylmethyl)-8-(phenyl-2-pyridinylmethylene)-4,7-methano-1H-isoindole-1,3(2H)-dione;McN 1025;S 6999;Compound S 6999;5-[(α-hydroxy-α-2-pyridyl)benzyl]-7-[α-(2-pyridyl)benzyl]-5-norbornene-2,3-dicarboximide;Norbormide;Raticate;5-(α-Hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide;Shoxin;NSC 101316;14841-34-0

Description

White solid. Insoluble in water; soluble in dilute acids. Nonyl trichlorosilane is a clear fuming liquid. Irritating odor.


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


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

Norbormide Basic Attributes

511.57000

511.57

213-589-6

K4085589CZ

2588

DTXSID8042216

CRYSTALS FROM METHYLENE CHLORIDE + ETHER|COLORLESS TO OFF-WHITE CRYSTALLINE POWDER|White solid|White crystals

Characteristics

92.18000

4.61820

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

1.346g/cm3

190-198 °C

780.539ºC at 760 mmHg

>230 °F

1.69

60mg/L(room temperature)

LD50 in rats (mg/kg): 5.3 orally; 0.65 i.v. (Roszkowski)

A MIXTURE OF STEREOISOMERS|Hydrolyzed by alkalis.

No rapid reaction with air. No rapid reaction with water.

Alcohols and Polyols

When heated to decomposition, NORBORMIDE emits toxic fumes of nitrogen oxides. Avoid alkalis. [EPA, 1998].

Non-corrosive

Safety Information

I

6.1(a)

2588

3

22

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S45:In case of accident or if you feel unwell, seek medical advice immediately

RB8750000

Xn

IT IS...STABLE @ ROOM TEMP WHEN DRY, AND TO BOILING WATER; HYDROLYZED BY ALKALI.

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))

When heated to decomposition, it emits toxic fumes of nitrogen oxides. Avoid alkalies. (EPA, 1998)

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

(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. (Non-Specific -- Pesticide, Solid, n.o.s.) Small fires: dry chemical, carbon dioxide, water spray, or foam. Large fires: water spray, fog, or foam. Move container from fire area if you can do so without risk. (EPA, 1998)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

(Non-Specific -- Pesticide, Solid, n.o.s.) Do not touch spilled material; stop leak if you can do so without risk. Small spills: absorb with sand or other noncombustible absorbent material and place into containers for later disposal. Small dry spills: with clean shovel place material into clean, dry container and cover; move containers from spill area. Large spills: dike far ahead of spill for later disposal. (EPA, 1998)

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)

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.

Toxicity

LD50 Rat oral 5.3 mg/kg|LD50 Rat iv 0.65 mg/kg|LD50 Norway rat oral 5.3-15.0 mg/kg /wild and domestic/|LD50 roof rat oral 52 mg/kg|For more Non-Human Toxicity Values (Complete) data for NORBORMIDE (9 total), please visit the HSDB record page.

Norbormide's use as a rodenticide for the control of rat (Rattus) species(1) will result in its release to the environment(SRC).

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).

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).

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).

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).

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).

Occupational 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)

Drug Information

2-5. 2= SLIGHTLY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-15 G/KG, BETWEEN 1 PINT AND 1 QT FOR 70 KG PERSON (150 LB). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ AND 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON AND 1 OZ FOR 70 KG PERSON (150 LB). 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 5-50 MG/KG, BETWEEN 7 DROPS AND 1 TEASPOONFUL FOR 70 KG PERSON (150 LB).

Substances used to destroy or inhibit the action of rats, mice, or other rodents. (See all compounds classified as Rodenticides.)

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 ... .

Moderately 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)

Note: Poisoning by norbormide is unlikely due to its low toxicity in humans (selectively toxic to rats). Signs and Symptoms of Norbormide Exposure: Signs and symptoms of acute exposure to norbormide may include headache, dizziness, and nausea. Humans exposed to doses up to 300 mg have presented with only mild reductions in systolic blood pressure and a slight lowering of body temperature. Emergency Life-Support Procedures: Acute exposure to norbormide may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to norbormide. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to norbormide. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of norbormide is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step 4. Ipecac should not be administered to children under 6 months of age.Warning: Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step 4.The following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. 6. Transport to a health care facility. (EPA, 1998)

For immediate first aid: Ensure that adequate decontamination has been carried out. If victim is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|For basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Monitor for shock and treat if necessary ... Anticipate seizures and treat if necessary ... For eye contamination, flush eye immediately with water. Irrigate each eye continuously with normal saline during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. ... Cover skin burns with sterile dressings after decontamination ... . /Poisons A and B/

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.

5-(alpha-hydroxy-alpha-2-pyridylbenzyl)-7- (alpha-2-pyridylbenzylidene)-5-norbornene-2,3- dicarboximide

Norbormide Use and Manufacturing

Methods of Manufacturing

...BY CONDENSATION OF 2-BENZOYLPYRIDINE & CYCLOPENTADIENE FOLLOWED BY REACTION OF THE OBTAINED FULVENE WITH MALEIMIDE.

Uses

Rodenticide.

'RATICATE', CONCENTRATE (5-10 G AI/KG) FOR BAIT PREPN IN CEREAL OFFALS, FISH MEAL, ETC.|CONTAINED FORMERLY IN THE PREPARATION RATICATE...|Bait concentrate

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.

PRODUCT ANALYSIS IS BY UV SPECTROMETRY.|Analysis of products: extraction in alkaline medium with chloroform, transfer into 0.1N hydrochloric acid, and UV-spectrometric determination of the absorption maxima at 300 and 240 nm (Clarke J Pharm Pharmacol 1965, 17, 126).

Computed Properties

Molecular Weight:511.6
XLogP3:3.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:511.18959167
Monoisotopic Mass:511.18959167
Topological Polar Surface Area:92.2
Heavy Atom Count:39
Complexity:1040
Undefined Atom Stereocenter Count:5
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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