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Identification
Name Amyl Nitrite
Accession Number DB01612
Type small molecule
Groups approved
Description

Amyl Nitrite is an antihypertensive medicine. Amyl nitrite is employed medically to treat heart diseases such as angina and to treat cyanide poisoning. 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 psychoactive effect which has led to illegal drug use.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
Amyl nitrosum
Isoamyl nitrite
n-Amyl nitrite
n-pentyl nitrite
Nitramyl
Pentyl nitrite
Salts Not Available
Brand names
Name Company
Aspiral
Vaporole
Brand mixtures Not Available
Categories
  • Vasodilator Agents
CAS number 110-46-3
Weight Average: 117.1463
Monoisotopic: 117.078978601
Chemical Formula C5H11NO2
InChI Key InChIKey=CSDTZUBPSYWZDX-UHFFFAOYSA-N
InChI
InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3
Plain Text
IUPAC Name
pentyl nitrite
SMILES
CCCCCON=O
Plain Text
Mass Spec show (9.66 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the rapid relief of angina pectoris.
Pharmacodynamics Amyl nitrite, in common with other alkyl nitrites, is a potent vasodilator. It expands blood vessels, resulting in lowering of the blood pressure. Alkyl nitrite 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.
Mechanism of action Amyl nitrite's antianginal action is thought to be the result of a reduction in systemic and pulmonary arterial pressure (afterload) and decreased cardiac output because of peripheral vasodilation, rather than coronary artery dilation. As an antidote (to cyanide poisoning), amyl nitrite promotes formation of methemoglobin, which combines with cyanide to form nontoxic cyanmethemoglobin.
Absorption Amyl nitrite vapors are absorbed rapidly through the pulmonary alveoli, manifesting therapeutic effects within one minute after inhalation.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Hepatic. The drug is metabolized rapidly, probably by hydrolytic denitration; approximately one-third of the inhaled amyl nitrite is excreted in the urine.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Overdose symptoms include nausea, emesis (vomiting), hypotension, hypoventilation, dyspnea (shortness of breath), and syncope (fainting)
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Liquid Oral
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State liquid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 3.97e+00 g/l ALOGPS
logP 1.98 ALOGPS
logP 2.31 ChemAxon
logS -1.5 ALOGPS
pKa (strongest basic) -1.8 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 38.66 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 31.68 ChemAxon
polarizability 12.84 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00517 Link_out
KEGG Compound C07457 Link_out
ChEBI 55344 Link_out
ChEMBL 55344 Link_out
PharmGKB PA164750570 Link_out
Drug Product Database 677930 Link_out
RxList http://www.rxlist.com/cgi/generic/amylnitrite.htm Link_out
Drugs.com http://www.drugs.com/cons/amyl-nitrite-inhalation-oral-nebulization.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Amyl_nitrite Link_out
ATC Codes
  • V03AB22
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Dihydroergotamine Possible antagonism of action
Ergotamine Possible antagonism of action
Methysergide Possible antagonism of action
Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Food Interactions Not Available
Targets

1. Atrial natriuretic peptide receptor A

Pharmacological action: yes
Actions: agonist

Receptor for atrial natriuretic peptide. Has guanylate cyclase activity on binding of ANF

Organism class: human
UniProt ID: P16066 Link_out
Gene: NPR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Madhani M, Scotland RS, MacAllister RJ, Hobbs AJ: Vascular natriuretic peptide receptor-linked particulate guanylate cyclases are modulated by nitric oxide-cyclic GMP signalling. Br J Pharmacol. 2003 Aug;139(7):1289-96. Pubmed
  2. Bauersachs J: Aminoethyl nitrate—the novel super nitrate? Br J Pharmacol. 2009 Sep;158(2):507-9. Pubmed
Enzymes

1. Aldehyde dehydrogenase, mitochondrial

Actions: substrate
UniProt ID: P05091 Link_out
Gene: ALDH2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Badejo AM Jr, Hodnette C, Dhaliwal JS, Casey DB, Pankey E, Murthy SN, Nossaman BD, Hyman AL, Kadowitz PJ: Mitochondrial aldehyde dehydrogenase mediates vasodilator responses of glyceryl trinitrate and sodium nitrite in the pulmonary vascular bed of the rat. Am J Physiol Heart Circ Physiol. 2010 Sep;299(3):H819-26. Epub 2010 Jun 11. Pubmed
Comments
Drug created on August 29, 2007 14:03 / Updated on February 08, 2013 16:20