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Identification
NameAmyl Nitrite
Accession NumberDB01612
TypeSmall Molecule
GroupsApproved
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
Synonyms
SynonymLanguageCode
1-NitropentaneNot AvailableNot Available
Amyl nitriteNot AvailableNot Available
Amyl nitrosumNot AvailableNot Available
Isoamyl nitriteNot AvailableNot Available
n-Amyl nitriteNot AvailableNot Available
n-pentyl nitriteNot AvailableNot Available
NitramylNot AvailableNot Available
Pentyl nitriteNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AspiralNot Available
VaporoleNot Available
Brand mixturesNot Available
Categories
CAS number110-46-3
WeightAverage: 117.1463
Monoisotopic: 117.078978601
Chemical FormulaC5H11NO2
InChI KeyCSDTZUBPSYWZDX-UHFFFAOYSA-N
InChI
InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3
IUPAC Name
pentyl nitrite
SMILES
CCCCCON=O
Mass Specshow(9.66 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassOrganic Oxoanionic Compounds
SubclassOrganic Nitrites
Direct parentOrganic Nitrites
Alternative parentsPolyamines
Substituentspolyamine
Classification descriptionThis compound belongs to the organic nitrites. These are organic compounds containing the nitrite oxoanion, with the formula NO2-.
Pharmacology
IndicationFor the rapid relief of angina pectoris.
PharmacodynamicsAmyl 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 actionAmyl 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.
AbsorptionAmyl nitrite vapors are absorbed rapidly through the pulmonary alveoli, manifesting therapeutic effects within one minute after inhalation.
Volume of distributionNot Available
Protein bindingNot 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 eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOverdose symptoms include nausea, emesis (vomiting), hypotension, hypoventilation, dyspnea (shortness of breath), and syncope (fainting)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9773
Caco-2 permeable + 0.526
P-glycoprotein substrate Non-substrate 0.6604
P-glycoprotein inhibitor I Non-inhibitor 0.7026
P-glycoprotein inhibitor II Non-inhibitor 0.9824
Renal organic cation transporter Non-inhibitor 0.7921
CYP450 2C9 substrate Non-substrate 0.8507
CYP450 2D6 substrate Non-substrate 0.7958
CYP450 3A4 substrate Non-substrate 0.5675
CYP450 1A2 substrate Non-inhibitor 0.6096
CYP450 2C9 substrate Non-inhibitor 0.7695
CYP450 2D6 substrate Non-inhibitor 0.8751
CYP450 2C19 substrate Non-inhibitor 0.7554
CYP450 3A4 substrate Non-inhibitor 0.9522
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7004
Ames test AMES toxic 0.9107
Carcinogenicity Carcinogens 0.7429
Biodegradation Ready biodegradable 0.962
Rat acute toxicity 2.8290 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.5604
hERG inhibition (predictor II) Non-inhibitor 0.773
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
LiquidOral
TabletOral
PricesNot Available
PatentsNot Available
Properties
Stateliquid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.97ALOGPS
logP1.98ALOGPS
logP2.31ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.66 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity31.68 m3·mol-1ChemAxon
Polarizability12.84 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00517
KEGG CompoundC07457
ChEBI55344
ChEMBL
PharmGKBPA164750570
Drug Product Database677930
RxListhttp://www.rxlist.com/cgi/generic/amylnitrite.htm
Drugs.comhttp://www.drugs.com/cons/amyl-nitrite-inhalation-oral-nebulization.html
WikipediaAmyl_nitrite
ATC CodesV03AB22
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
DihydroergotaminePossible antagonism of action
ErgotaminePossible antagonism of action
MethysergidePossible antagonism of action
TreprostinilAdditive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Food InteractionsNot Available

Targets

1. Atrial natriuretic peptide receptor 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Atrial natriuretic peptide receptor 1 P16066 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Aldehyde dehydrogenase, mitochondrial P05091 Details

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

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Drug created on August 29, 2007 14:03 / Updated on September 16, 2013 17:15