Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H11NO2 |
Molecular Weight | 117.1463 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)CCON=O
InChI
InChIKey=OWFXIOWLTKNBAP-UHFFFAOYSA-N
InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3
ISOPENTYL NITRITE (Amyl nitrite) is a chemical compound with an amyl group attached to the nitrite functional group. Amyl nitrite, in common with other alkyl nitrites, is a potent vasodilator; it expands blood vessels, resulting in lowering of the blood pressure. Alkyl nitrites are a source of nitric oxide, which signals for relaxation of the involuntary muscles. Physical effects include the 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 internal and external anal sphincter. There are no withdrawal symptoms. Overdose symptoms include nausea, vomiting, hypotension, hypoventilation, shortness of breath, and fainting. The effects set in very quickly, typically within a few seconds and disappear within a few minutes. Amyl nitrite may also intensify the experience of synesthesia. Amyl nitrite is employed medically to treat heart diseases as well as angina. Amyl nitrite is sometimes used as an antidote for cyanide poisoning. It can act as an oxidant, to induce the formation of methemoglobin. Methemoglobin, in turn, can sequester cyanide as cyanomethemoglobin.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0042311 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | AMYL NITRITE Approved UseINDICATIONS AND USAGE: Amyl nitrite is indicated for the rapid relief of angina pectoris. Its effect appears within 30 seconds and lasts for approximately 3 to 5 minutes. |
PubMed
Title | Date | PubMed |
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Inhibition of lipid peroxidation in synaptosomes and liposomes by nitrates and nitrites. | 2002 Jul |
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Organic nitrites and NO: inhibition of lipid peroxidation and radical reactions. | 2004 Feb |
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Nitrosation of sugar oximes: preparation of 2-glycosyl-1-hydroxydiazene-2-oxides. | 2005 Dec 23 |
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Synthesis of peroxynitrite using isoamyl nitrite and hydrogen peroxide in a homogeneous solvent system. | 2006 Jul 15 |
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New modular and efficient approach to 6-substituted pyridin-2-yl C-nucleosides. | 2006 Sep 15 |
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anti-Tricyclo-[4.2.1.1]deca-3,7-diene-9-endo,10-endo-diol. | 2008 Nov 8 |
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A facile access to [60]fullerene-fused delta-lactones: unexpected reaction pathway of benzenediazonium-2-carboxylates controlled by organic bases. | 2009 Apr 7 |
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Photolysis of n-butyl nitrite and isoamyl nitrite at 355 nm: a time-resolved Fourier transform infrared emission spectroscopy and ab initio study. | 2009 May 7 |
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Peroxynitrite modifies the structure and function of the extracellular matrix proteoglycan perlecan by reaction with both the protein core and the heparan sulfate chains. | 2010 Jul 15 |
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2,6-Dichloro-pyridine-3,5-dicarbonitrile. | 2010 Sep 25 |
Sample Use Guides
Adults: 0.3 milliliter (1 ampul) taken by inhaling the vapor of amyl nitrite through the nose. Dose may be repeated within 1 to 5 minutes if pain is not relieved. If you still have chest pain after a total of 2 doses in a 10-minute period, contact your doctor or have someone take you to a hospital emergency room without delay.
Route of Administration:
Respiratory
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C29707
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SUBSTANCE RECORD