Isoamyl nitrite Chemical Properties

Boiling point:

99 °C(lit.)

Density 

0.872 g/mL at 25 °C(lit.)

vapor pressure 

35-59.995hPa at 20-25℃

refractive index 

n20/D 1.386(lit.)

Flash point:

50 °F

storage temp. 

Store at +15°C to +25°C.

solubility 

Chloroform (Soluble), Methanol (Slightly)

form 

Liquid

color 

Clear yellow

Water Solubility 

<0.01 g/100 mL at 18 ºC

Sensitive 

Air & Light Sensitive

Merck 

14,5123

BRN 

969510

Stability:

Unstable. Air and light sensitive. Flammable. Forms explosive mixtures with air or oxygen. Incompatible with oxidizing agents, reducing agents.

InChIKey

OWFXIOWLTKNBAP-UHFFFAOYSA-N

LogP

2.45-2.85

CAS DataBase Reference

110-46-3(CAS DataBase Reference)

NIST Chemistry Reference

Amyl Nitrite(110-46-3)

EPA Substance Registry System

Isoamyl nitrite (110-46-3)

Safety Information

Hazard Codes 

F,Xn

Risk Statements 

11-20/22

Safety Statements 

16-24-46

RIDADR 

UN 1113 3/PG 2

WGK Germany 

1

RTECS 

NT0187500

F 

1-8-9

Autoignition Temperature

208 °C

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29209090

Hazardous Substances Data

110-46-3(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 505 mg/kg

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Isoamyl nitrite Usage And Synthesis

Antianginal drugs

Light yellow transparent liquid, ether-like smell with fruity. It volatiles at room temperature, and is easy to burn. It is insoluble in water, can be mixed with alcohol, ether, chloroform or benzene arbitrary at any ratio. In case of light and air it will break down.
Isoamyl nitrite, also known as amyl nitrite, is the fastest onset, and the shortest duration of anti-anginal drugs, is a sub-short-acting nitrates vasodilator, its pharmacological effects is similar to nitroglycerin, it can directly relax vascular smooth muscle, especially for small vascular smooth muscle, make systemic vasodilation, reduce peripheral resistance, blood pressure, reduce venous return blood, reduce cardiac output, thereby reduce myocardial oxygen consumption, anti-angina and effectively stimulate sexual desire. Because of its rapid hydrolysis in the gastrointestinal tract, so this product is oral invalid, drugs used clinically are usually made on a volatile liquid pharmaceutical inhalants, rapidly absorbed in the lungs after inhalation, it can be effective less than half a minute , lasts for only 3 to 10 minutes, the anti-anginal effect nitroglycerin similar, but inhaled dose of this product is difficult to control, and the adverse reaction is large, which is its shortcomings. Because it often causes severe headache, severe hypotension and tachycardia, it is now rarely used in clinical treatment of angina and biliary colic, gradually being replaced by other nitrates.
[Adverse reactions and Precautions]
Common adverse reactions are headache, facial flushing, hypotension and reflex tachycardia ect. Isoamyl nitrite owns severe reaction than nitroglycerin.
Excessive use dosage can cause low blood pressure and heart rate, increase symptoms of angina, heart rate and blood pressure should be closely observed during intravenous drug using. Due to excessive methemoglobin poisoning, symptoms include cyanosis, breathing difficulty and other symptoms of hypoxia, intravenous injection of 1% methylene blue is used for first aid, along with oxygen , and blood transfusions.
Usinge for head trauma, brain hemorrhage, acute coronary thrombosis is banned.
Using in coronary occlusion and increased intracranial pressure is banned.

Cyanide poisoning antidote

Pharmacological effects are the same with sodium nitrite, isoamyl nitrite is also an oxidizing agent, hemoglobin is oxidized to be high iron (Fe3 +) hemoglobin combines with cyanide ions to form cyanide methemoglobin, eliminates blood free cyanide ions on cytochrome oxidase enzyme infringement, but also makes the cytochrome oxidase bound cyanide ion release, leading to the enzyme activity and tissue respiration function recovery, it should be used simultaneously with sodium thiosulfate to bind with cyanide methemoglobin to form non-toxic thiocyanate group (SCN-) and excreted, and thus play a role in the treatment of cyanide poisoning. This product is administrated by inhalation, rapidly absorbed in the lungs, displays the effects after inhalation of 10 to 30 seconds, the role lasts for 3 to 5 minutes. For emergency use, sodium nitrite is intravenous injected until the symptoms improve.
The above information is edited by the Chemicalbook of Tian Ye.

Chemical Properties

Light yellow clear liquid having a boiling point of 99 °C, the relative density is 0.871 (20/4 ℃), the refractive index is 1.3871, the flash point is 10 ℃. It is soluble with alcohol, ether, it can not dissolve in water. With fruit flavor. With volatility, it will break down in the case of light and air .

Uses

It is used in synthesizing perfumes, drugs and diazo compounds. It can be used as an oxidizing agent, solvent. Isobutyl nitrite ester is a drug that is the the fastest short-acting nitrates vasodilator. It is also used as hydrocyanic acid and its salts poisoning antidote.Vasodilators, for the treatment of angina pectoris, also it is used for cyanide poisoning; it is used in synthesizing perfumes, drugs and diazo compounds. It can be used as an oxidizing agent, solvent.

Production method

It is derived from isoamyl alcohol and sodium nitrite. According to the actual production situation, it may have a different method of operation. 1. The reaction takes place in the reaction tube, in synthetic aqueous solution of sodium nitrite, isoamyl alcohol, hydrochloric acid, respectively, are put into the high slot. First sodium nitrite solution and hydrochloric acid solution are dropped at the same rate into the synthesis pipe, when the chlorine gas bubbles in the pipe,isoamyl alcohol is slowly dropped from the top of the pipe, that is in the pipeline synthetic crude. Washed, dried, fractionated to get the products. 2. The reaction is carried out in a reaction tank of sodium nitrite, isoamyl alcohol and water are added to the reaction pot, stirring, cooling to 5 ℃, solution of hydrochloric acid is dropped. At 5 ℃ insulation for 1h, after standing hours to remove the water layer, acetate layer is washed with water, then washed with sodium carbonate solution, and then washed with water. After removing the layer of water, it is dehydrated with anhydrous sodium carbonate, filtered. The filtrate is distilled, collecting 97-99 ℃ distillate, to get isoamyl nitrite.

Category

Flammable liquid

Toxicity grading

Highly toxic

Acute toxicity

Oral-rat LD50: 505 mg/kg; inhalation-mouse LC50: 1430 PPM/30 min

Explosive hazardous characteristics

Heating can be explosive

Flammability hazard characteristics

In the case of fire, high temperature, oxidant, it is flammable; in the case of light, heat may generate toxic nitric oxide gas.

Storage characteristics

Treasury should be ventilation, low-temperature and dry; It should be stored separately from oxidants and acids.

Extinguishing agent

Dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent.

Description

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’).

Chemical Properties

Isoamyl Nitrite is flammable and explosive and decomposes when exposed to air and sunlight.

Chemical Properties

Amyl nitrites are flammable, yellowish liquid with a penetrating, fruity odor. Sp.Gr. 0.88. B.P. 99℃. Slightly soluble in water, miscible with alcohol and oils.

Uses

Isopentyl nitrite is used in the conversion of 2,6-disubstituted phenols to diphenoquinones and aminophenols to quinone diazides. It acts as an oxidant and nitrosating agent. It finds application in aromatic arylation, deamination of arylamines using tetrahydrofuran as a hydrogen donor. It is also useful for the preparation of benzyne using anthranilic acid. It is an antihypertensive and vasodilator to treat heart diseases such as angina and an antidote for cyanide poisoning. Further, it is used as a solvent and cleaning agent for a printed circuit board. In addition to this, it is considered to be a replacement for freon.

Uses

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.

Uses

Vasodilator.

Preparation

Isoamyl nitrite is produced from iso-Amyl alcohol, Sodium nitrite, water and diluted Sulfuric acid.

Definition

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.

General Description

Clear yellow liquid.

Air & Water Reactions

Highly flammable. Decomposes on exposure to air and light. Insoluble in water.

Reactivity Profile

Isoamyl nitrite is an oxidizing agent but can serve as a reducing agent. Forms explosive mixtures with air or oxygen. .

Hazard

Flammable, dangerous fire risk, a strong oxidizer. Vapor may explode if ignited.

Fire Hazard

Isoamyl nitrite is flammable.

Potential Exposure

Amyl nitrite is used to make pharmaceuticals; perfumes, diazonium compounds, and other chemicals.

Environmental Fate

The primary mechanism of toxicity develops from the powerful oxidative effects of nitrites on hemoglobin. Methemoglobinemia, which develops when the iron atom in hemoglobin loses one electron to an oxidant, causing a change from the ferrous (2+) state to the ferric (3+) state, may cause cellular hypoxia. When methemoglobin levels exceed 10–15%, cyanosis may be evident. Nitrites also cause vasodilation by direct action on smooth muscle. Physical effects include decreases in blood pressure, headache, flushing of the face, increased heart rate, dizziness, and relaxation of involuntary muscles, especially of the blood vessels and the anal sphincter.
Amyl nitrite may be irritating to the lungs and throat when breathed in. With exposure to the skin, amyl nitrite has irritant properties. It can also be readily absorbed, causing systemic effects with skin contact.

Shipping

UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.

Toxicity evaluation

A volatile liquid, amyl nitrite is slightly soluble in water and is commonly supplied in ampoules that are broken and administered by inhalation. Inhalation is likely the most common route of exposure, though reports of ingestion of the liquid itself have been seen. Amyl nitrite may also be absorbed through the skin when skin comes in contact with the liquid.Amyl nitrite is an unstable compound. It is air and light sensitive and flammable. Amyl nitrite forms explosive mixtures with air or oxygen, and it is incompatible with oxidizing agents and reducing agents.

Incompatibilities

Vapors may form explosive mixture with air. Slowly decomposes in light, heat, and on contact with water. A strong oxidizer. Contact with reducing agents and easily oxidizable materials may cause fire and explosions. Reported to be an explosion hazard when exposed to air and light. Keep away from alcohols, antipyrine, alkaline materials; alkaline carbonates; potassium iodide; bromides, and ferrous salts. Attacks metals in the presence of moisture.

Waste Disposal

Incineration with scrubber to remove nitrogen oxides from the combustion gases.

Isoamyl nitrite(110-46-3)Related Product Information

• Isoamyl o-hydroxybenzoate
• AMYL NITRITE,N-AMYL NITRITE
• POTASSIUM NITRITE
• Calcium nitrite
• 3-Methyl-1-butanol
• NITROUS ACID
• Sodium nitrite
• Isoamyl benzoate
• Isobutyl nitrite
• tert-Butyl nitrite
• 1-Butyl nitrite
• ISOPROPYL NITRITE
• SODIUM NITRITE-15N
• SODIUM COBALTINITRITE
• Trilostane
• N-PROPYL NITRITE
• Nitrite ion standard solution
• Nitrite solution standard substance