Amyl nitrite
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| Amyl nitrite | |
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| General | |
| Systematic name | 3-methyl-1-nitrosooxybutane |
| Other names | Isoamyl nitrite Nitramyl 3-methyl-1-nitrosooxybutane Pentyl alcohol nitrite(ambiguous) Nitrous acid, pentyl ester(ambiguous) |
| Molecular formula | C5H11NO2 |
| SMILES | |
| Molar mass | 117.15 g/mol |
| Appearance | Colourless liquid |
| CAS number | [110-46-3] |
| Properties | |
| Density and phase | 0.872 g/cm3, liquid (25 °C) |
| Solubility in water | Low |
| Other solvents | soluble in organic solvents |
| Melting point | ?? °C |
| Boiling point | 99 °C |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | vasodialator |
| NFPA 704 | ? |
| R/S statement | R: 11-20/22 S: 16-24-46 |
| RTECS number | NT0187500 |
| Flash point | 21 °C |
| Supplementary data page | |
| Structure and properties]] |
n = 1.386 |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds | nitroglycerine isopentanol Butyl nitrite Ethyl nitrite |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references |
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Amyl nitrite, also referred to as pentyl nitrite, is an alkyl nitrite that contains five carbons. Typically, the term refers to the chemical compound with the formula (CH3)2CHCH2CH2ONO. Like other volatile alkyl nitrites, it has a characteristically penetrating odour and produces marked effects on the human body when its vapor is inhaled. It acts as a vasodilator (expanding blood vessels and thus lowering blood pressure) and finds applications in medicine in the treatment of heart disease such as angina. Amyl nitrite is also used to treat cyanide poisoning by inducing the formation of methemoglobin, which sequesters cyanide as non-toxic cyanomethemoglobin.[1]
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[edit] Nomenclature
The term "amyl nitrite" encompasses a plurality of isomers. For example, a common form of amyl nitrite with the formula (CH3)2CHCH2CH2ONO may be more specifically referred to as isoamyl nitrite. A linear form of "amyl nitrite" may have the structural formula CH3(CH2)4ONO.
[edit] Synthesis and reactions
Alkyl nitrites are prepared by the reaction of alcohols with nitrous acid.[2] The reaction is analogous to esterification. The resulting isoamyl nitrite decomposes in the presence of base to give nitrite salts and the isoamyl alcohol:
- RCH2ONO + NaOH → RCH2OH + NaNO2
Amyl nitrite, like other nitrite esters, reacts with carbanions to give oximes.[3]
[edit] Physiological effects
Amyl nitrite, in common with other alkyl nitrites, is a potent vasodilator that functions as a source of nitric oxide, which signals for relaxation of the involuntary muscles. Physical effects include decrease in blood pressure, headache, flushing of the face, increased heart rate, dizziness, and relaxation of involuntary muscles, especially the blood vessel walls and the anal sphincter. There are no withdrawal symptoms. Overdose symptoms include nausea, emesis (vomiting), hypotension, hypoventilation, dyspnea (shortness of breath), and syncope (fainting). Clinically, amyl nitrite is prescribed for unstable angina [4] and acute cyanide poisoning.
[edit] Popular culture
Amyl nitrite capsules were developed by Alton J. Parker. Although intended for medicinal use, they are used recreationally as inhalants (See Nitrite inhalants), and are often called "poppers".[5] Marcel Proust reputedly used amyl nitrite before bedtime because it helped his asthma, and characters in Hunter S. Thompson's Fear and Loathing in Las Vegas used amyl nitrite recreationally. In "The Adventure of the Resident Patient", a Sherlock Holmes story of Sir Arthur Conan Doyle, Dr. Trevelyan considers the use of amyl nitrite for an elderly man suffering a seizure. In the film 'Fight Club', a cancer sufferer named Chloe tries to attract a final sexual partner before she dies - she mentions that she has amyl nitrite in her apartment, among other things. In Jeffrey Eugenides book 'The Virgin Suicides', vials of amyl nitrite are one of the objects given to Trip Fontaine by his droves of female admirers.
[edit] References
- ^ Vale, J. A. (2001). "Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin - Which Antidote is Best?". Toxicology 168 (1): 37-38.
- ^ Noyes, W. A. “n-Butyl Nitrite” Organic Syntheses, Collected Volume 2, p.108 (1943). http://www.orgsyn.org/orgsyn/pdfs/CV2P0108.pdf
- ^ Chen, Y. K.; Jeon, S.-J; Walsh, P. J.; Nugent, W. A. “(2S)-(-)-3-exo-(Morpholino)isoborneol ((-)-MIB)” Organic Syntheses, Vol. 82, p.87 (2005). http://www.orgsyn.org/orgsyn/pdfs/v82p0087.pdf
- ^ Cheng, L.; Goodwin, C. A.; Schully, M. F.; Kakkar, V. V.; Claeson, G. (1965). "The Effects of Nitroglycerin and Amyl Nitrite on Arteriolar and Venous Tone in the Human Forearm". Circulation 3 (2): 755.
- ^ Slavin, S. (2001). "Recreational Use of Amyl Nitrite". Venerology - The interdisciplinary International Journal of Sexual Health 14 (2): 81-82.
[edit] External links
- Links to external chemical sources
- Abstract for an article in the Journal of Chemical Education (1996, volume 73, page 1127) by Richard A. Kjonaas on the use of the word "amyl".
| Alkyl nitrites edit |
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Amyl nitrite | Butyl nitrite | Ethyl nitrite | Methyl nitrite | Isopropyl nitrite | Isobutyl nitrite | Cyclohexyl nitrite |
