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ECHA InfoCard | 100.008.057 |
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Formula | C4H9NO2 |
Molar mass | 103.121 g·mol−1 |
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Boiling point | 78.0 °C (172.4 °F) |
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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.
It can be prepared by treating nitrous acid (generated in situ ) with n-butanol. [1]
Butyl nitrite is one of the compounds used as poppers, inhalant drugs that induce brief euphoria. It was developed by Clifford Hassing, [2] [3] a graduate student in Los Angeles, as a faster-acting analog of alkyl nitrite. Among the inhalants' trade names are Rush, Locker Room, and Bolt. They are sometimes marketed as "Cleaner", liquid incense, or room odorizer. It is used for its euphoric effect and for relaxing the smooth muscles during sexual intercourse. [2] [3]
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 was first documented in 1844 and came into medical use in 1867.
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 cocaine are not, even though these drugs are inhaled as smoke or vapor.
Nitrous acid is a weak and monoprotic acid known only in solution, in the gas phase and in the form of nitrite salts. It was discovered by Carl Wilhelm Scheele, who called it "phlogisticated acid of niter". Nitrous acid is used to make diazonium salts from amines. The resulting diazonium salts are reagents in azo coupling reactions to give azo dyes.
The nitrite ion has the chemical formula NO−
2. Nitrite is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also refers to organic compounds having the –ONO group, which are esters of nitrous acid.
The chemical compound isopropyl nitrite is an alkyl nitrite made from isopropanol. It is a clear pale yellow oil that is insoluble in water.
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 recreational drug of the chemical class called alkyl nitrites that are inhaled. They act on the body as vasodilators. Most widely sold products include the original isoamyl nitrite, 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.
Nitrosation is a process of converting organic compounds into nitroso derivatives, i.e., compounds containing the R-NO functionality.
1-Bromobutane is the organobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.
The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). The method involves the reaction of an α-amino-ketone (1) and a compound containing an electron-withdrawing group α to a carbonyl group (2).
Isobutyl nitrite, C4H9NO2, is an alkyl nitrite, an ester of isobutanol and nitrous acid. Its chemical structure is (CH3)2CH-CH2-ONO.
Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride. This pyrocarbonate reacts with amines to give N-tert-butoxycarbonyl or so-called Boc derivatives. These carbamate derivatives do not behave as amines, which allows certain subsequent transformations to occur that would be incompatible with the amine functional group. The Boc group can later be removed from the amine using moderately strong acids. Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. Boc-protected amines are unreactive to most bases and nucleophiles, allowing for the use of the fluorenylmethyloxycarbonyl group (Fmoc) as an orthogonal protecting group.
In organic chemistry, alkyl nitrites are a group of organic compounds based upon the molecular structure R−O−N=O, where R represents an alkyl group. Formally they are alkyl esters of nitrous acid. They are distinct from nitro compounds.
The Barton reaction, also known as the Barton nitrite ester reaction, is a photochemical reaction that involves the photolysis of an alkyl nitrite to form a δ-nitroso alcohol.
Butyl nitrate is a colorless oil. It is often confused with butyl nitrite, which is sometimes used as a recreational inhalant.
Dinitrogen trioxide is the inorganic compound with the formula N2O3. It is a nitrogen oxide. It forms upon mixing equal parts of nitric oxide and nitrogen dioxide and cooling the mixture below −21 °C (−6 °F):
2-Chlorobutane is a compound with formula C4H9Cl. It is also called sec-butyl chloride. It is a colorless, volatile liquid at room temperature that is not miscible in water.
Nitrolic acids are organic compounds with the functional group RC(NO2)=NOH. They are prepared by the reaction of nitroalkanes with base and nitrite sources:
tert-Butyl nitrite is an organic compound with the formula (CH3)3CONO. A colorless liquid, it is the tert-butyl ester of nitrous acid. It is typically employed as a solution with tert-butyl alcohol.
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.