| Fluoroform | |
|---|---|
 
| |
| 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 | |
Amyl nitrite 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 vapour is inhaled. It is 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]
Nomenclature
Amyl nitrite is a misnomer, it should be called isoamyl nitrite. The chemical named "amyl nitrite" has the structural formula CH3(CH2)4ONO. Other compounds with closely related names and formulae also exist.
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]
Physiological effects
Amyl nitrite, along 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, increase in pulse 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 (throwing up), hypotension, hypoventilation, dyspnea (shortness of breath), and syncope (fainting). Clinically, amyl nitrite is prescribed for unstable angina. [4]
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.
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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Slavin, S. (2001). "Recreational Use of Amyl Nitrite". Venerology - The interdisciplinary International Journal of Sexual Health. 14 (2): 81–82.
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".