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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AspiralNot Available
VaporoleNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkyl nitrites. These are organic compounds containing an alkyl group linked to a nitrite group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic nitrites
Direct ParentAlkyl nitrites
Alternative Parents
Substituents
  • Alkyl nitrite
  • O-nitroso compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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. Amyl nitrite is a source of nitric acid, which accounts for the mechanism described above. 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
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9773
Caco-2 permeable+0.526
P-glycoprotein substrateNon-substrate0.6604
P-glycoprotein inhibitor INon-inhibitor0.7026
P-glycoprotein inhibitor IINon-inhibitor0.9824
Renal organic cation transporterNon-inhibitor0.7921
CYP450 2C9 substrateNon-substrate0.8507
CYP450 2D6 substrateNon-substrate0.7958
CYP450 3A4 substrateNon-substrate0.5675
CYP450 1A2 substrateNon-inhibitor0.6096
CYP450 2C9 substrateNon-inhibitor0.7695
CYP450 2D6 substrateNon-inhibitor0.8751
CYP450 2C19 substrateNon-inhibitor0.7554
CYP450 3A4 substrateNon-inhibitor0.9522
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7004
Ames testAMES toxic0.9107
CarcinogenicityCarcinogens 0.7429
BiodegradationReady biodegradable0.962
Rat acute toxicity2.8290 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5604
hERG inhibition (predictor II)Non-inhibitor0.773
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.97 mg/mLALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.66 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesV03AB22
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AvanafilPhosphodiesterase 5 Inhibitors may enhance the vasodilatory effect of Amyl Nitrite.
ButabarbitalMay enhance the hypotensive effect of Hypotensive Agents.
ButethalMay enhance the hypotensive effect of Hypotensive Agents.
DuloxetineHypotensive Agents may enhance the orthostatic hypotensive effect of DULoxetine.
HeptabarbitalMay enhance the hypotensive effect of Hypotensive Agents.
HexobarbitalMay enhance the hypotensive effect of Hypotensive Agents.
MethohexitalMay enhance the hypotensive effect of Hypotensive Agents.
Nitric OxideMay enhance the adverse/toxic effect of Methemoglobinemia Associated Agents. Combinations of these agents may increase the likelihood of significant methemoglobinemia.
PentobarbitalMay enhance the hypotensive effect of Hypotensive Agents.
PrilocaineMethemoglobinemia Associated Agents may enhance the adverse/toxic effect of Prilocaine. Combinations of these agents may increase the likelihood of significant methemoglobinemia.
PrimidoneMay enhance the hypotensive effect of Hypotensive Agents.
RiociguatAmyl Nitrite may enhance the hypotensive effect of Riociguat.
RisperidoneHypotensive Agents may enhance the hypotensive effect of RisperiDONE.
SecobarbitalMay enhance the hypotensive effect of Hypotensive Agents.
SildenafilPhosphodiesterase 5 Inhibitors may enhance the vasodilatory effect of Amyl Nitrite.
TadalafilPhosphodiesterase 5 Inhibitors may enhance the vasodilatory effect of Amyl Nitrite.
VardenafilPhosphodiesterase 5 Inhibitors may enhance the vasodilatory effect of Amyl Nitrite.
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