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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
1-nitropentane
n-Amyl nitrite
n-pentyl nitrite
Nitramyl
pentyl nitrite
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amyl Nitrite Vitrellae Bpc Liq 0.33 Ml/capliquid0.33 mlinhalationShire Pharma Canada Ulc1997-04-012001-10-01Canada
Amylnitrite Glass Cap 5minliquid.3 mlinhalationAllen & Hanburys A Glaxo Canada Ltd. Co.1951-12-311999-08-06Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amyl Nitriteinhalant.3 g/.3mLrespiratory (inhalation)James Alexander Corporation1979-02-07Not applicableUs
International Brands
NameCompany
AspiralNot Available
VaporoleNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII22T8Z09XAK
CAS number8017-89-8
WeightAverage: 117.1463
Monoisotopic: 117.078978601
Chemical FormulaC5H11NO2
InChI KeyInChIKey=CSDTZUBPSYWZDX-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.
Related Articles
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 inhibitorNon-inhibitor0.7695
CYP450 2D6 inhibitorNon-inhibitor0.8751
CYP450 2C19 inhibitorNon-inhibitor0.7554
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Inhalantrespiratory (inhalation).3 g/.3mL
Liquidinhalation0.33 ml
Liquidinhalation.3 ml
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)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesV03AB22
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Amyl Nitrite.
AvanafilAvanafil may increase the vasodilatory activities of Amyl Nitrite.
ButabarbitalButabarbital may increase the hypotensive activities of Amyl Nitrite.
ButethalButethal may increase the hypotensive activities of Amyl Nitrite.
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Amyl Nitrite.
DuloxetineAmyl Nitrite may increase the orthostatic hypotensive activities of Duloxetine.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Amyl Nitrite.
HexobarbitalHexobarbital may increase the hypotensive activities of Amyl Nitrite.
LevodopaAmyl Nitrite may increase the orthostatic hypotensive activities of Levodopa.
MethohexitalMethohexital may increase the hypotensive activities of Amyl Nitrite.
NicorandilNicorandil may increase the hypotensive activities of Amyl Nitrite.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Amyl Nitrite.
PentobarbitalPentobarbital may increase the hypotensive activities of Amyl Nitrite.
PrilocaineThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Prilocaine.
PrimidonePrimidone may increase the hypotensive activities of Amyl Nitrite.
RiociguatAmyl Nitrite may increase the hypotensive activities of Riociguat.
RisperidoneAmyl Nitrite may increase the hypotensive activities of Risperidone.
SecobarbitalSecobarbital may increase the hypotensive activities of Amyl Nitrite.
SildenafilSildenafil may increase the vasodilatory activities of Amyl Nitrite.
Sodium NitriteThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Sodium Nitrite.
TadalafilTadalafil may increase the vasodilatory activities of Amyl Nitrite.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Amyl Nitrite.
VardenafilVardenafil may increase the vasodilatory activities of Amyl Nitrite.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein kinase activity
Specific Function:
Receptor for the atrial natriuretic peptide NPPA/ANP and the brain natriuretic peptide NPPB/BNP which are potent vasoactive hormones playing a key role in cardiovascular homeostasis. Has guanylate cyclase activity upon binding of the ligand.
Gene Name:
NPR1
Uniprot ID:
P16066
Molecular Weight:
118918.11 Da
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:12890708 ]
  2. Bauersachs J: Aminoethyl nitrate--the novel super nitrate? Br J Pharmacol. 2009 Sep;158(2):507-9. doi: 10.1111/j.1476-5381.2009.00414.x. [PubMed:19732062 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Electron carrier activity
Specific Function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular Weight:
56380.93 Da
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. doi: 10.1152/ajpheart.00959.2009. Epub 2010 Jun 11. [PubMed:20543077 ]
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Drug created on August 29, 2007 14:03 / Updated on August 17, 2016 12:23