Isobutyl nitrite

Last updated
Isobutyl nitrite [1]
Isobutyl nitrite Structural Formula V1.svg
Isobutyl nitrite 3d structure.png
Names
Preferred IUPAC name
2-Methylpropyl nitrite
Other names
Isobutyl nitrite
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.018 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3 Yes check.svgY
    Key: APNSGVMLAYLYCT-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3
    Key: APNSGVMLAYLYCT-UHFFFAOYAF
  • O=NOCC(C)C
Properties
C4H9NO2
Molar mass 103.11976
AppearanceColorless liquid
Odor Almond-like [2]
Density 0.87 g/mL
Boiling point 67 °C (153 °F; 340 K)
Slightly soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isobutyl nitrite, C4H9NO2, is an alkyl nitrite, an ester of isobutanol and nitrous acid. Its chemical structure is (CH3)2CH-CH2-ONO.

Contents

Isobutyl nitrite is a pungent colorless liquid. It acts as a vasodilator, and is used as an inhalant recreational drug, poppers.

Applications

Isobutyl nitrite is one of the compounds used as poppers, an inhalant drug that induces a brief euphoria. Also, it is used as part of the antidote package for cyanide poisoning.[ medical citation needed ]

Safety

May cause headaches, dizziness and fainting. Isobutyl nitrite is poisonous to people with glucose-6-phosphate dehydrogenase deficiency. [3]

Related Research Articles

<span class="mw-page-title-main">Amyl nitrite</span> Chemical compound

Amyl nitrite is a chemical compound with the formula C5H11ONO. A variety of isomers are known, but they all feature an amyl group attached to the nitrite functional group. The alkyl group is unreactive and the chemical and biological properties are mainly due to the nitrite group. Like other alkyl nitrites, amyl nitrite is bioactive in mammals, being a vasodilator, which is the basis of its use as a prescription medicine. As an inhalant, it also has a psychoactive effect, which has led to its recreational use, with its smell being described as that of old socks or dirty feet. It is also referred to as banapple gas.

<span class="mw-page-title-main">Inhalant</span> Chemical, often household, breathed in to cause intoxication

Inhalants are a broad range of household and industrial chemicals whose volatile vapors or pressurized gases can be concentrated and breathed in via the nose or mouth to produce intoxication, in a manner not intended by the manufacturer. They are inhaled at room temperature through volatilization or from a pressurized container, and do not include drugs that are sniffed after burning or heating. For example, amyl nitrite (poppers), nitrous oxide and toluene – a solvent widely used in contact cement, permanent markers, and certain types of glue – are considered inhalants, but smoking tobacco, cannabis, and crack are not, even though these drugs are inhaled as smoke or vapor.

<span class="mw-page-title-main">Club drug</span> Category of recreational drugs

Club drugs, also called rave drugs or party drugs, are a loosely defined category of recreational drugs which are associated with discothèques in the 1970s and nightclubs, dance clubs, electronic dance music (EDM) parties, and raves in the 1980s to today. Unlike many other categories, such as opiates and benzodiazepines, which are established according to pharmaceutical or chemical properties, club drugs are a "category of convenience", in which drugs are included due to the locations they are consumed and/or where the user goes while under the influence of the drugs. Club drugs are generally used by adolescents and young adults.

<span class="mw-page-title-main">Glucose-6-phosphate dehydrogenase deficiency</span> Medical condition

Glucose-6-phosphate dehydrogenase deficiency (G6PDD), which is the most common enzyme deficiency worldwide, is an inborn error of metabolism that predisposes to red blood cell breakdown. Most of the time, those who are affected have no symptoms. Following a specific trigger, symptoms such as yellowish skin, dark urine, shortness of breath, and feeling tired may develop. Complications can include anemia and newborn jaundice. Some people never have symptoms.

<span class="mw-page-title-main">Pentose phosphate pathway</span> Metabolic process

The pentose phosphate pathway is a metabolic pathway parallel to glycolysis. It generates NADPH and pentoses as well as ribose 5-phosphate, a precursor for the synthesis of nucleotides. While the pentose phosphate pathway does involve oxidation of glucose, its primary role is anabolic rather than catabolic. The pathway is especially important in red blood cells (erythrocytes).

<span class="mw-page-title-main">Butyl nitrite</span> Chemical compound

Butyl nitrite is the organic compound with the formula CH3(CH2)3ONO. It is an alkyl nitrite made from n-butanol. Butyl nitrite is used recreationally as poppers. Synonyms include 1-butyl nitrite, n-butyl nitrite and nitrous acid butyl ester.

<span class="mw-page-title-main">Isopropyl nitrite</span> Chemical compound

The chemical compound isopropyl nitrite is an alkyl nitrite made from isopropanol. It is a clear pale yellow oil that is insoluble in water.

<span class="mw-page-title-main">Cyclohexyl nitrite</span> Chemical compound

Cyclohexyl nitrite is an organic compound, with formula C6H11NO2. It is the ester of cyclohexanol and nitrous acid, i.e. it is an alkyl nitrite. Like amyl nitrite and butyl nitrite, it acts as an antianginal due to vasodilation. The compound is colorless, volatile liquid.

Popper is a slang term given broadly to drugs of the chemical class called alkyl nitrites that are inhaled. Most widely sold products include the original isoamyl nitrite or isopentyl nitrite, and isopropyl nitrite. Isobutyl nitrite is also widely used but is banned in the European Union. In some countries, poppers are labeled or packaged as room deodorizers, leather polish, nail polish remover, or videotape head cleaner to evade anti-drug laws.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Glucose-6-phosphate dehydrogenase</span> Enzyme involved in the production of energy by cells

Glucose-6-phosphate dehydrogenase (G6PD or G6PDH) (EC 1.1.1.49) is a cytosolic enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">6-phosphogluconolactonase</span> Cytosolic enzyme

6-Phosphogluconolactonase (EC 3.1.1.31, 6PGL, PGLS, systematic name 6-phospho-D-glucono-1,5-lactone lactonohydrolase) is a cytosolic enzyme found in all organisms that catalyzes the hydrolysis of 6-phosphogluconolactone to 6-phosphogluconic acid in the oxidative phase of the pentose phosphate pathway:

In enzymology, a glucose 1-dehydrogenase (NADP+) (EC 1.1.1.119) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Phosphogluconate dehydrogenase (decarboxylating)</span>

In enzymology, a phosphogluconate dehydrogenase (decarboxylating) (EC 1.1.1.44) is an enzyme that catalyzes the chemical reaction

In enzymology, a glucose 1-dehydrogenase is an enzyme that catalyzes the chemical reaction

In enzymology, a quinoprotein glucose dehydrogenase is an enzyme that catalyzes the chemical reaction

CDP-4-dehydro-6-deoxyglucose reductase (EC 1.17.1.1) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">6-phosphogluconate dehydrogenase deficiency</span> Medical condition

6-Phosphogluconate dehydrogenase deficiency, or partial deficiency, is an autosomal hereditary disease characterized by abnormally low levels of 6-phosphogluconate dehydrogenase (6PGD), a metabolic enzyme involved in the Pentose phosphate pathway. It is very important in the metabolism of red blood cells (erythrocytes). 6PDG deficiency affects less than 1% of the population, and studies suggest that there may be race variant involved in many of the reported cases. Although it is similar, 6PDG deficiency is not linked to glucose-6-phosphate dehydrogenase (G6PD) deficiency, as they are located on different chromosomes. However, a few people have had both of these metabolic diseases.

Glucose-6-phosphate dehydrogenase (coenzyme-F420) is an enzyme with systematic name D-glucose-6-phosphate:F420 1-oxidoreductase. This enzyme catalyses the following chemical reaction

Hexyl nitrite has the formula C6H13NO2 and is a nitrite and more specifically, an alkyl nitrite. It is an ester of hexanol and nitrous acid. It has the structural formula of: CH3(CH2)5ONO The CAS Registry Number is 638-51-7 and the European Community number 680-102-5. It is REACH and TSCA registered. It is also known as nitrous acid, hexyl ester. It is the aliphatic analogue of cyclohexyl nitrite.

References

  1. Merck Index , 11th Edition, 5032.
  2. CDC - NIOSH Pocket Guide to Chemical Hazards
  3. Bubp, Jeff; Jen, Marilyn; Matuszewski, Karl (September 2015). "Caring for Glucose-6-Phosphate Dehydrogenase (G6PD)–Deficient Patients: Implications for Pharmacy". Pharmacy and Therapeutics. 40 (9): 572–574. ISSN   1052-1372. PMC   4571844 . PMID   26417175.