Amyl nitrite
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| Names | |
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| IUPAC name
(3-methylbutyl) nitrite
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| Other names
Isoamyl nitrite
Nitramyl 3-methyl-1-nitrosooxybutane Pentyl alcohol nitrite(ambiguous) Nitrous acid, pentyl ester(ambiguous) poppers (colloquial, street slang) | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.003.429 |
PubChem CID
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| RTECS number |
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CompTox Dashboard (EPA)
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| Properties | |
| C5H11NO2 | |
| Molar mass | 117.148 g·mol−1 |
| Appearance | Colourless liquid |
| Density | 0.872 g/cm3, liquid (25 °C) |
| Boiling point | 99 °C |
| Low | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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vasodilator |
| Flash point | 21 °C |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Amyl nitrite is the chemical compound with the formula C5H11ONO. A variety of isomers are known, but they all feature an amyl group attached to the nitrito 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.
Nomenclature
The term "amyl nitrite" encompasses several isomers. For example, a common form of amyl nitrite with the formula (CH3)2CHCH2CH2ONO may be more specifically referred to as isoamyl nitrite. When the amyl group is a linear or normal (n) alkyl group, the resulting amyl nitrite would have the structural formula CH3(CH2)4ONO.
Amyl nitrite is often confused with amyl nitrate, a substance with a different chemical composition and different properties.
Synthesis and reactions
Alkyl nitrites are prepared by the reaction of alcohols with nitrous acid:[1]
- C5H11OH + HONO → C5H11ONO + H2O
The reaction is called esterification. Synthesis of alkyl nitrites is, in general, straightforward and can be accomplished in home laboratories. A common procedure includes the dropwise addition of concentrated sulfuric acid to a cooled mixture of an aqueous sodium nitrite solution and an alcohol. The intermediately-formed stoichiometric mixture of nitrous and nitric oxide then converts the alcohol to the alkyl nitrite, which, due to its low density, will form an upper layer that can be easily decanted from the reaction mixture.
Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the isoamyl alcohol:
- C5H11ONO + NaOH → C5H11OH + NaNO2
Amyl nitrite, like other alkyl nitrites, reacts with carbanions to give oximes.[2]
Physiological effects
Amyl nitrite, in common with other alkyl nitrites,[3] is a potent vasodilator, i.e., it expands blood vessels, resulting in lowering of the blood pressure. Alkyl nitrites function 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). The effects set in very quickly, typically within a few seconds and disappearing soon after (within a minute).
It induces the formation of methemoglobin, which sequesters cyanide as non-toxic cyanomethemoglobin.[4]
Applications
Amyl nitrite is employed medically to treat heart diseases such as angina and also to treat cyanide poisoning.[5] It is also used as an inhalant drug that induces a brief euphoria state, and when combined with other intoxicated stimulant drugs such as cocaine or ecstasy (see MDMA), the euphoric state intensifies and lasts for several minutes longer. Once some stimulative drugs wear off, a common side-effect is a period of depression or anxiety, colloquially called a "come down"; amyl nitrite is sometimes used to "come up" again in order to stop the user from feeling lousy. This effect, combined with its dissociative effects, makes it an attractive but risky recreational drug (see poppers).[6]
Another common use is as an additive booster propellant for model diesel engines.
References
- ^ Noyes, W. A. “n-Butyl Nitrite” Organic Syntheses, Collected Volume 2, p.108 (1943). [1] (PDF)
- ^ Chen, Y. K.; Jeon, S.-J; Walsh, P. J.; Nugent, W. A. “(2S)-(-)-3-exo-(Morpholino)isoborneol ((-)-MIB)” Organic Syntheses, Volume 82, pp. 87 (2005). [2] (PDF)
- ^ Nickerson, Mark, John O Parker, Thomas P Lowry, and Edward W Swenson. Isobutyl Nitrite and Related Compounds. 1st ed. San Francisco: Pharmex, Ltd, 1979. [3] PDF
- ^ Vale, J. A. (2001). "Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin - Which Antidote is Best?". Toxicology. 168 (1): 37–38.
- ^ 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ AJ Giannini, AE Slaby, MC Giannini. The Handbook of Overdose and Detoxification Emergencies. New Hyde Park, NY. Medical Examination Publishing Co., 1982, pp.48-50.
External links
- 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".