Isoamyl nitrite

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

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.

Chemical properties

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

The Uses of Isoamyl nitrite

Vasodilator.

The Uses of Isoamyl nitrite

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.

The Uses of Isoamyl nitrite

To ACN (350 mL) at RT was added CuBr2 (67 g, 300 mmol). The mixture was cooled to 0-5 C and was treated dropwise with t-BuONO (72.5 mL, 535 mmol). The mixture was stirred for 5 min, then was added the SM (35 g, 238 mmol). The reaction was stirred at RT for 2 h. EtOAc (525 mL) was added to the mixture and the reaction was quenched with 10% aq NH4Cl (350 mL) and 2% aq NH3 (175 mL). The layers were separated and the aq layer was extracted with EtOAc. The combined organics were dried and concentrated. The resulting material was purified by silica gel chromatography (eluting with 5% EtOAc/hexane) to provide the product as a yellow solid. [35 g, 70%]

The Uses of Isoamyl nitrite

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.

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.

What are the applications of Application

Isopentyl nitrite is a compound for vascular research

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.