亜硝酸イソアミル

Isoamyl Nitrite

HCID 8053CAS 110-46-3

基本情報

標準SMILES
CC(C)CCON=O
InChIKey
OWFXIOWLTKNBAP-UHFFFAOYSA-N
分子式
C5H11NO2
平均分子量
117.15 g/mol
単同位体質量
117.07897859

名称と識別子

優先名称
Isoamyl Nitrite
IUPAC
3-methylbutyl nitrite
現地名
亜硝酸イソアミル
英語名
Isoamyl nitrite
分子式
C5H11NO2
分子量
117.15

名称と別名

ISOAMYL NITRITEIsopentyl nitrite110-46-33-Methylbutyl nitriteVaporoleAmilnitriteAspiralNitrous acid, 3-methylbutyl ester3-Methylbutanol nitritePentanoli nitrisNitrous acid, isopentyl esterIsopentyl alcohol, nitrite
名称をさらに表示
亜硝酸イソアミル亜硝酸イソペンチルアスピラル1-ニトロソオキシ-3-メチルブタンバポロールニトラミル亜硝酸3-メチルブチルイソアミル ニトリト亜硝酸イソアミル(亜硝酸イソペンチル)亜硝酸アミル (JP17)亜硝酸アミルAMYL NITRITEamylamyl nitrite, mixed isomersIsoamyl nitrite,97%,stabilizedIsoaMyl nitrite, 96%, stabilizedIsopentyl nitrite, 97%, stab. with 0.2% anhyd. sodium carbonate
Amyl nitrosumDTXSID90254555N0U5TUC9ZNSC-7903CHEBI:2691DTXCID402605Nitrite, AmylRefChem:54193

データベース識別子

CAS
110-46-3、8017-89-8
PubChem CID
8053
DTXSID
DTXSID9025455
ChEMBL
CHEMBL1535371
ChEBI
CHEBI:2691
UNII
5N0U5TUC9Z
EC Number
203-770-8
Nikkaji
J5.092J

物性

構造計算による物性

XLogP
1.7
極性表面積
38.7 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
3
重原子数
8

実験および物理化学的性質

OdorPenetrating fragrant, somewhat fruity odor
TastePungent, aromatic taste
Density · 4 件

0.8528 at 68 °F (NTP, 1992) - Less dense than water; will float

0.875 @ 25 °C

Relative density (water = 1): 0.875

0.8828 @ 20°C

Color/FormYellowish, transparent liquid
Solubility · 4 件

less than 0.1 mg/mL at 64 °F (NTP, 1992)

MISCIBLE WITH ETHER, ALCOHOL, CHLOROFORM

Very slightly soluble in water

Solubility in water: none

Flash Point · 2 件

less than 69 °F (NTP, 1992)

3 °C

物理化学的性質

融点
-80 °C · <-80°C
沸点
99 °C · 99 °C(lit.)
比重(密度)
0.872 g/mL · 0.872 g/mL at 25 °C(lit.)
蒸気圧
35 · 35-59.995hPa at 20-25℃
屈折率
20 · n20/D 1.386(lit.)
闪点
50 °F · 50 °F

化学的性質

化学的特性Isoamyl Nitrite is flammable and explosive and decomposes when exposed to air and sunlight.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids];H302: Harmful if swallowed [Warning Acute toxicity, oral];H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Danger

危険有害性情報

Regulatory Information · 3 件

Status: Active Update: 26-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27335;Status: Active Update: 10-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30183

Nitrous acid, 3-methylbutyl ester: HSNO Approval: HSR001086 Approved with controls

The 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.)

Other Safety InformationIMAP assessments - Nitrous acid, 3-methylbutyl ester: Environment tier I assessment;IMAP assessments - Nitrous acid, 3-methylbutyl ester: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 件

This chemical is flammable. (NTP, 1992)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;· Vapors may form explosive mixtures with air.;· Vapors may travel to source of ignition and flash back.;· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapor explosion hazard indoors, outdoors or in sewers.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Runoff to sewer may create fire or explosion hazard.;· Containers may explode when heated.;· Many liquids will float on water.

Highly flammable. Many reactions may cause fire or explosion. Heating will cause rise in pressure with risk of bursting. Vapour/air mixtures are explosive.

Fire Potential · 2 件

Moderate, when exposed to heat or flame or by spontaneous chemical reaction...can react with oxidizing...material.

Caution--amyl nitrite is very flammable. Do not use where it may be ignited.

Health Hazards · 2 件

SYMPTOMS: Exposure to this chemical can cause flushing of the skin, rapid pulse, headache, dizziness, weakness and a drop in blood pressure.;ACUTE/CHRONIC HAZARDS: This chemical is readily absorbed through the skin. It forms explosive mixtures with air; therefore, all sources of ignition should be eliminated before opening the container. (NTP, 1992)

· May cause toxic effects if inhaled or absorbed through skin.;· Inhalation or contact with material may irritate or burn skin and eyes.;· Fire will produce irritating, corrosive and/or toxic gases.;· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.;· Runoff from fire control or dilution water may cause environmental contamination.

安全と保護具

Fire Fighting · 2 件

Fires involving this material can be controlled with a dry chemical, carbon dioxide, foam or Halon extinguisher. (NTP, 1992)

Use water spray, alcohol-resistant foam. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

First Aid Measures · 4 件

Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.;· All equipment used when handling the product must be grounded.;· Do not touch or walk through spilled material.;· Stop leak if you can do it without risk.;· Prevent entry into waterways, sewers, basements or confined areas.;· A vapor-suppressing foam may be used to reduce vapors.;· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.;· Use clean, non-sparking tools to collect absorbed material.;Large Spill;· Dike far ahead of liquid spill for later disposal.;· Water spray may reduce vapor, but may not prevent ignition in closed spaces.

First Aid · 2 件

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.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· Wash skin with soap and water.

Safe StorageFireproof. Separated from strong oxidants. Cool. Well closed.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).;· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

毒性情報

Interactions...Its effect can be antagonized by any drug that can activate smooth muscle under consideration. Thus, nitrite is functional antagonist of norepinephrine, acetylcholine, histamine... /nitrite/
Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Exposure RoutesThe substance can be absorbed into the body by inhalation and through the skin.
Signs and Symptoms · 3 件

Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Sweating. Nausea. Unconsciousness. Vomiting. Flushing of the face. Symptoms may be delayed.

MAY BE ABSORBED!

See Inhalation.

Human Toxicity Excerpts · 2 件

/HUMAN EXPOSURE STUDIES/ Adverse effects from nitrate and nitrite overdosage are extensions of the pharmacologic action of the drugs, namely the capacity to induce vasodilation, venous pooling, reduced cardiac output, and hypotension. Nitrate and nitrite overdosage may result in severe hypotension, tachycardia, bradycardia, heart-block, palpitation, death secondary to circulatory collapse, confusion, fever, syncope (especially in upright posture), persistent throbbing headache, visual disturbances, increased intracranial pressure, paralysis, and coma followed by seizures, flushing and diaphoresis, cold and clammy skin, nausea and vomiting, colic and diarrhea, dyspnea, and methemoglobinemia. /Nitrates and nitrites/

/HUMAN EXPOSURE STUDIES/ Heart rate responses to inhalation of amyl nitrite by patient during acute adrenergic beta blockade with iv propranolol varied greatly from patient to patient but because of its marked hypotensive effect it proved to be very potent stimulus for heart rate incr.

Non-Human Toxicity Excerpts · 3 件

/LABORATORY ANIMALS: Acute Exposure/ Inhalation of small amt of vapor causes ...in some... animals slight momentary rise in intraocular pressure.

/LABORATORY ANIMALS: Acute Exposure/ Liq amyl nitrite tested on normal rabbit eyes causes only slight superficial injury.

/GENOTOXICITY/ Isoamyl nitrite was found to be positive when tested for mutagenicity using the Salmonella/microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). Isoamyl nitrite was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 0.010, 0.033, 0.100, 0.333, 1.000, 3.333, and 6.666 mg/plate. The lowest positive dose tested in any S. typhimurium strain was 0.100 mg/plate in strain TA1535 with 10% rat liver S-9. Slight to total clearing of the background bacterial lawn was exhibited in cultures containing the two highest doses.

法規制情報

Regulatory Information · 3 件

Status: Active Update: 26-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27335;Status: Active Update: 10-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30183

Nitrous acid, 3-methylbutyl ester: HSNO Approval: HSR001086 Approved with controls

The 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.)

安全データ

F
1-8-9
wgk
1
tsca
TSCA listed
rtecs
NT0187500
ridadr
UN 1113 (AMYL NITRITE)
毒性
LD50 orally in Rabbit: 505 mg/kg

化学と産業

薬理情報

ATC Code · 2 件

V - Various;V03 - All other therapeutic products;V03A - All other therapeutic products;V03AB - Antidotes;V03AB22 - Amyl nitrite

QV - Various;QV03 - All other therapeutic products;QV03A - All other therapeutic products;QV03AB - Antidotes;QV03AB22 - Amyl nitrite

Pharmacodynamics · 1 件

Amyl nitrite, in common with other alkyl nitrites, is a potent vasodilator. It expands blood vessels, resulting in lowering of the blood pressure. Alkyl nitrite functions as a source of nitric oxide, which signals for relaxation of the involuntary muscles. Adverse effects are related to this pharmacological activity and include hypotension, headache, flushing of the face, tachycardia, dizziness, and relaxation of involuntary muscles, especially the blood vessel walls and the anal sphincter.

Mechanism of Action · 1 件

Amyl nitrite's antianginal action is thought to be the result of a reduction in systemic and pulmonary arterial pressure (afterload) and decreased cardiac output because of peripheral vasodilation, rather than coronary artery dilation. Amyl nitrite is a source of nitric oxide, which accounts for the mechanism described above. As an antidote (to cyanide poisoning), amyl nitrite promotes formation of methemoglobin, which combines with cyanide to form nontoxic cyanmethemoglobin.

Metabolism/Metabolites · 2 件

Hepatic. The drug is metabolized rapidly, probably by hydrolytic denitration; approximately one-third of the inhaled amyl nitrite is excreted in the urine.

Amyl nitrite ... probably is rapidly hydrolyzed to isoamyl alcohol and nitrite ion.

MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
Absorption, Distribution and Excretion · 3 件

Amyl nitrite vapors are absorbed rapidly through the pulmonary alveoli, manifesting therapeutic effects within one minute after inhalation.

Amyl nitrite is readily absorbed via the respiratory tract...

Approx 1/3 of the inhaled amy nitrite is excreted in the urine.

用途と製造

Uses · 5 件

Used in perfumes and to make diazonium compounds; Also used as a drug (vasodilator for angina and antidote for hydrogen cyanide poisoning); [HSDB]

Used in perfumes; preparation of diazonium compounds

Used as a vasodilator in angina therapy in the treatment of hydrogen cyanide and hydrogen sulfide poisonings, and as an industrial chemical and perfume scent

MEDICATION

MEDICATION (VET)

U.S. Exports · 3 件

(1972) No Data

(1975) No Data

(1986) No Data

U.S. Imports · 3 件

(1972) No Data

(1975) No Data

(1986) No Data

U.S. Production · 3 件

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1986) No Data

Consumption Patterns100% AS A CARDIOVASCULAR DILATOR (1973)
Methods of Manufacturing · 2 件

Reaction of isoamyl alcohol and nitrous acid.

Prepared by nitrosation of isopentyl alcohol ... .

応用分野 · 5 件

解説C5H11NO2(117.15).(CH3)2CHCH2CH2ONO.イソペンチルアルコールに塩化ニトロシルNOClを作用させるか,塩化イソペンチルに亜硝酸銀を作用させると得られる.淡黄色の果実臭をもつ揮発性液体.沸点97~99 ℃.冷暗所に保存する.容易に加水分解されて亜硝酸となるので,ジアゾニウム塩,ニトロソ,およびイソニトロソ化合物の合成に用いられる.血管拡張,平滑筋弛緩などの作用をもち,医薬品として狭心症に用いられる.亜硝酸イソペンチルを主成分として,ペンチルアルコール部分の異性体を含むものを,薬局方で亜硝酸イソアミルとよんでいる.森北出版「化学辞典(第2版)

用途ニトロソ化あるいはジアゾニウム塩の合成試薬

説明Amyl nitrite had been used clinically as early as 1867, when the Scottish physician Sir Thomas Brunton used it as a vasodilator as treatment for angina pectoris in his patients. In the late 1880s, a protective effect on cyanide toxicity in canines was noted when amyl nitrite was inhaled postexposure. Amyl nitrite has been used clinically in a multicomponent cyanide antidote kit and is also a recreational drug of abuse (‘poppers’).

使用Isoamyl nitrite is a light yellow, transparent liquid with a pleasant, fragrant, fruity odor. Amyl nitrite was introduced to medicine in 1859 and has been under considerable pharmacological investigation since that time. Its major use was for treating angina pectoris through its vasodilative effect on the coronary arteries. However, this effect is transient, and nitroglycerin and longer acting nitrates have largely replaced it. Amyl nitrite has been most helpful in clarifying the differential diagnosis of murmurs. For example, left ventricular outflowobstruction increases followingamyl nitrite administration. Mitral regurgitation decreases following amyl nitrite as does the apical diastolic rumble of mitral stenosis. The Austin–Flint rumble decreases followingamyl nitrite as does a ventricular septal defect and acyanotic tetralogy of Fallot. Pulmonic stenosis increases as does isolated valvular pulmonary stenosis following amyl nitrite. Isoamyl nitrite has also been reportedly used for inhalation abuse. The symptoms following inhalation of large doses by humans are flushing of the face, pulsatile headache, disturbing tachycardia, cyanosis (methemoglobinemia), weakness, confusion, restlessness, faintness, and collapse, particularly if the individual is standing. The symptoms are usually of short duration. Industrial intoxication has not been reported.

一般的な説明Clear yellow liquid.

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補足説明

定義ChEBI: Isoamyl nitrite is a nitrite ester having isopentyl as the alkyl group. It has a role as a vasodilator agent and an antihypertensive agent. It derives from an isoamylol.

関連反応

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