亜硝酸イソブチル

Isobutyl nitrite

HCID 10958

基本情報

CAS
542-56-3
標準SMILES
CC(C)CON=O
InChIKey
APNSGVMLAYLYCT-UHFFFAOYSA-N
分子式
C4H9NO2
平均分子量
103.12 g/mol
単同位体質量
103.06332853

概要

Isobutyl Nitrite can cause cancer according to The National Toxicology Program.

名称と識別子

優先名称
Isobutyl nitrite
IUPAC
2-methylpropyl nitrite
現地名
亜硝酸イソブチル
英語名
Isobutyl nitrite
分子式
C4H9NO2
分子量
103.12

名称と別名

ISOBUTYL NITRITE542-56-3Nitrous acid, 2-methylpropyl esterNitrous acid, isobutyl esterDTXSID3020750NCI-C61052GW9WAB6QOMDTXCID70750CHEBI:46643RefChem:7916382-methylpropyl nitrite;isobutyl nitrite208-819-7
名称をさらに表示
亜硝酸イソブチル亜硝酸2-メチルプロピルイソブチルニトリル[[[亜硝酸イソブチル2-メチルプロピル ニトリットisobutyl nitrilei-Butyl nitriteIsobutylnitrite, stabilized with anhydrous 0.5% sodium carbonateIsobutylnitrite,94%,stabilized with anhydrous0.5% sodium carbonateIsobutylnitrite, 94%, stabilized with 0.5%anhydrous sodium carbonate
Isobutylnitrite2-methylpropyl nitritenitrous acid 2-methylpropyl esterIsobutylnitritIBNMFCD00002056(CH3)2CHCH2ONOBlackjack

データベース識別子

CAS
542-56-3
PubChem CID
10958
DTXSID
DTXSID3020750
ChEMBL
CHEMBL1526886
ChEBI
CHEBI:46643
UNII
GW9WAB6QOM
EC Number
208-819-7
Nikkaji
J4.509H

物性

構造計算による物性

XLogP
1.4
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
2
重原子数
7

実験および物理化学的性質

Chemical Classes · 2 件

Nitrogen Compounds -> Nitrates and Nitrites

Flammable agents - 3rd degree

SpringerMaterials PropertiesCoriolis coupling
Density · 4 件

0.87 at 72 °F (NTP, 1992) - Less dense than water; will float

0.870 AT 22 °C/4 °C

Relative density (water = 1): 0.87

0.87 at 72 °F

Color/FormCOLORLESS LIQUID
Solubility · 3 件

less than 1 mg/mL at 66 °F (NTP, 1992)

SLIGHTLY SOLUBLE AND GRADUALLY DECOMPOSED BY WATER; MISCIBLE WITH ALCOHOL

Solubility in water: very poor

Flash Point · 4 件

-10 °F (NTP, 1992)

-10 °F

-21 °C

-10 °F

物理化学的性質

沸点
66 · 66-67 °C(lit.)
比重(密度)
0.87 g/mL · 0.87 g/mL at 25 °C(lit.)
屈折率
20 · n20/D 1.373(lit.)
闪点
6 °F · −6 °F
貯蔵温度
0 · 0-6°C
外見
clear liquid

化学的性質

化学的特性Isobutyl nitrite is a colourless to pale yellow liquid and has a pleasant and fruity odor.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P318, P330, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P318, P330, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 2 件

Hazard Traits - Carcinogenicity

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.)

DOT LabelFlammable Liquid Poison
Fire Hazards · 2 件

This chemical is flammable. (NTP, 1992)

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include headache, dizziness and tachycardia. Other symptoms include carboxyhemoglobinemia, fall in blood pressure and change in heart rate.
Hazards Summary · 1 件

High doses cause death from methemoglobinemia in acute and subchronic animal studies. Delayed animal deaths were attributeed to hepatotoxicity; [ACGIH] Liver damage as a cause of death was suggested in one animal study. [HSDB] A volatile substance that may be abused by inhalation mainly for its vasodilator properties; [Reference #1]

Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

安全と保護具

Fire Fighting · 2 件

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

Use dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention .

First Aid · 1 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.

Safe StorageFireproof. Separated from acids. Well closed.
Exposure Control and Personal ProtectionBiological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing 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.

毒性情報

InteractionsPRETREATMENT WITH A SINGLE DOSE OF METHYLENE BLUE PREVENTS THE METHEMOGLOBIN FORMATION AND PROTECTS AGAINST THE LETHALITY OF THE BUTYL NITRITES IN MICE.
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms · 2 件

Sore throat. Headache. Dizziness. Blue lips, fingernails and skin. Nausea. Confusion. Convulsions. Unconsciousness. Symptoms may be delayed.

See Inhalation.

Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=542-56-3]

Human Toxicity Excerpts · 4 件

THOUGH THE USUAL ROUTE OF ADMINISTRATION BY INHALATION HAS NOT RESULTED IN ANY TOXICOLOGICALLY VERIFIED DEATHS, ISOBUTYL NITRITE MAY CAUSE FATAL TOXIC METHEMOGLOBINEMIA IF INGESTED. A CASE WITH A FATAL OUTCOME IS PRESENTED.

METHEMOGLOBINEMIA OCCURRED IN A 36-YR-OLD MAN WHO INGESTED 15 ML OF ISOBUTYL NITRITE (RUSH). HE RECOVERED AFTER TREATMENT WITH INTRAVENOUS 1% METHYLENE BLUE, 20 ML, INFUSED OVER 20 MINUTES.

A CASE REPORT OF SEVERE AND PROLONGED TRACHEOBRONCHITIS IN A 23-YR-OLD MALE, FOLLOWING THE INHALATION OF 2 BOTTLES OF LOCKER ROOM (ISOBUTYL NITRITE), IS PRESENTED.

AT A 1% ADDED CONCN, ISOBUTYL NITRITE LYSED HUMAN LEUKOCYTES AND REDUCED VIABILITY FROM 95 TO 21% IN 24 HR. AT LESS THAN OR EQUAL TO 0.5%, CELL COUNT AND VIABILITY WERE UNAFFECTED, BUT ISOBUTYL NITRITE INHIBITED IN VITRO LYMPHOCYTE BLASTOGENIC RESPONSES TO PHYTOHEMAGGLUTININ, POKEWEED MITOGEN, AND CONCANAVALIN A. IT INHIBITED NATURAL KILLER CELL ACTIVITY TO THE K562 CELL LINE, LYMPHOCYTE-MEDIATED ANTIBODY-DEPENDENT CELLULAR CYTOTOXICITY TO THE CEM CELL LINE, MONOCYTE-MEDIATED ANTIBODY-DEPENDENT CELLULAR CYTOTOXICITY TO HUMAN RED BLOOD CELLS, AND IN VITRO ADHERENCE AND TRANSFORMATION OF MONOCYTES TO MACROPHAGES. INHIBITORY EFFECTS WERE GREATER THAN 90% AT 0.5% AND STILL DETECTABLE AT 0.01%. ISOBUTYL NITRITE INHIBITED LEUCINE, URIDINE, AND THYMIDINE INCORPORATION APPROX EQUALLY. AFTER 24 HR OF EXPOSURE, THE EFFECTS ON VARIOUS LYMPHOCYTE FUNCTION PARAMETERS WERE NOT REVERSIBLE.

安全データ

wgk
3
tsca
TSCA listed
rtecs
RA0805000
ridadr
UN 2351 3/PG 2
hs_code
29209090
risk_code
45-11-20/22-68

化学と産業

薬理情報

MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.

用途と製造

Uses · 2 件

Used as a chemical intermediate and a drug for angina pectoris; [ACGIH] Amyl nitrite and isobutyl nitrite are used as illicit, aphrodisiac inhalants to enhance erection. [AHLS, p. 199]

USED TO A LIMITED EXTENT IN INDUSTRY AS INTERMEDIATES IN CHEMICAL SYNTHESES /ALIPHATIC NITRITES/

Methods of ManufacturingFROM ISOBUTYL ALCOHOL, SODIUM NITRITE, AND DILUTE SULFURIC ACID.
General Manufacturing InformationNitrous acid, 2-methylpropyl ester: ACTIVE
応用分野 · 5 件

解説亜硝酸イソブチル,特異臭のある液体.沸点67 ℃.d224 0.870.n22D1.3715.エタノール,エーテルなどの有機溶媒に可溶,水に微溶.徐々に加水分解を受ける.ニトロソ化剤やジアゾニウム塩の合成に用いられる.蒸気の吸入によって血管拡張や血圧降下などを引き起こす.森北出版「化学辞典(第2版)

用途芳香剤添加物 (NITE調査)カルボキシメチルセルロース原料、農薬?医薬原料 (SRI:CHEMICAL ECONOMICS HANDBOOK)可塑剤?医薬原料 (化学工業日報社)

使用Isobutyl nitrite is an alkyl nitrite. It is mainly used in “poppers”, consumed as a recreational drug for their psychoactive effects. Poppers are illegal in many countries, and as a result are commonly sold as air fresheners or deodorizers. Other minor uses of isobutyl nitrite include as an intermediate in the synthesis of aliphatic nitrites, nail polish removers, video head cleaners, fuels, and jet propellants.Isobutyl nitrite was used to study inhalant-induced immunotoxicity. It is used in the preparation of plasmoquin.

一般的な説明Isobutyl nitrite is an ester of isobutanol and nitrous acid, which has a various range of household and industrial applications. It is commonly added to a number of household cleaning liquids and air fresheners. As a volatile liquid, it also serves as a "room odorizer" which is widely sold without a prescription.Besides, Isobutyl nitrite has also been applied in pharmaceuticals, in which it acts as a vasodilator (blood vessel relaxant) and is used medically as part of the emergency antidote for cyanide poisoning.

使用用途亜硝酸イソブチルの主な使用用途は芳香剤の添加物です。カルボキシメチルセルロース原料、農薬・医薬原料、可塑剤・医薬原料にもなります。 また、血管拡張作用がある他、シアン中毒の解毒剤としても使われます。いわゆるラッシュ系ドラッグとしても認識されている物質です。平成19年に薬事法第2条第 14項に規定する指定薬物に指定されました。 医療用および人体に危害を及ぼすおそれのない用途以外での製造・輸入・販売等は禁止されています。尚、毒物及び劇物取締法では、劇物に指定されています。

調製方法

製造方法Isobutyl nitrite is synthesized by reacting isobutyl alcohol with sodium nitrite in dilute sulfuric acid (NTP, 1996).

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