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Identification
NameAmyl Nitrite
Accession NumberDB01612
TypeSmall Molecule
GroupsApproved
DescriptionAmyl 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
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Amyl Nitrite.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Amyl Nitrite.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Amyl Nitrite.
AliskirenThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Aliskiren.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Amyl Nitrite.
AmlodipineThe risk or severity of adverse effects can be increased when Amlodipine is combined with Amyl Nitrite.
AmobarbitalAmobarbital may increase the hypotensive activities of Amyl Nitrite.
ApraclonidineThe risk or severity of adverse effects can be increased when Apraclonidine is combined with Amyl Nitrite.
AripiprazoleAripiprazole may increase the hypotensive activities of Amyl Nitrite.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Amyl Nitrite.
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Azilsartan medoxomil.
BarbitalBarbital may increase the hypotensive activities of Amyl Nitrite.
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Amyl Nitrite.
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bendroflumethiazide is combined with Amyl Nitrite.
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Amyl Nitrite.
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Amyl Nitrite.
BretyliumThe risk or severity of adverse effects can be increased when Bretylium is combined with Amyl Nitrite.
BrimonidineThe risk or severity of adverse effects can be increased when Brimonidine is combined with Amyl Nitrite.
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Amyl Nitrite.
CanagliflozinThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Canagliflozin.
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Amyl Nitrite.
CaptoprilThe risk or severity of adverse effects can be increased when Captopril is combined with Amyl Nitrite.
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Amyl Nitrite.
CarvedilolThe risk or severity of adverse effects can be increased when Carvedilol is combined with Amyl Nitrite.
ChlorothiazideThe risk or severity of adverse effects can be increased when Chlorothiazide is combined with Amyl Nitrite.
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Amyl Nitrite.
CilazaprilThe risk or severity of adverse effects can be increased when Cilazapril is combined with Amyl Nitrite.
ClevidipineThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Clevidipine.
ClonidineThe risk or severity of adverse effects can be increased when Clonidine is combined with Amyl Nitrite.
DapagliflozinThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Dapagliflozin.
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Amyl Nitrite.
DexmedetomidineThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Amyl Nitrite.
DiclofenamideThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Amyl Nitrite.
DiltiazemThe risk or severity of adverse effects can be increased when Diltiazem is combined with Amyl Nitrite.
DinutuximabThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Dinutuximab.
DipyridamoleThe risk or severity of adverse effects can be increased when Dipyridamole is combined with Amyl Nitrite.
DoxazosinThe risk or severity of adverse effects can be increased when Doxazosin is combined with Amyl Nitrite.
DuloxetineAmyl Nitrite may increase the orthostatic hypotensive activities of Duloxetine.
EmpagliflozinThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Empagliflozin.
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Amyl Nitrite.
EplerenoneThe risk or severity of adverse effects can be increased when Eplerenone is combined with Amyl Nitrite.
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Amyl Nitrite.
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Amyl Nitrite.
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Amyl Nitrite.
FelodipineThe risk or severity of adverse effects can be increased when Felodipine is combined with Amyl Nitrite.
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Amyl Nitrite.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Amyl Nitrite.
GuanfacineThe risk or severity of adverse effects can be increased when Guanfacine is combined with Amyl Nitrite.
HexobarbitalHexobarbital may increase the hypotensive activities of Amyl Nitrite.
HydralazineThe risk or severity of adverse effects can be increased when Hydralazine is combined with Amyl Nitrite.
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Hydrochlorothiazide is combined with Amyl Nitrite.
IndapamideThe risk or severity of adverse effects can be increased when Indapamide is combined with Amyl Nitrite.
IrbesartanThe risk or severity of adverse effects can be increased when Irbesartan is combined with Amyl Nitrite.
Isosorbide DinitrateThe risk or severity of adverse effects can be increased when Isosorbide Dinitrate is combined with Amyl Nitrite.
Isosorbide MononitrateThe risk or severity of adverse effects can be increased when Isosorbide Mononitrate is combined with Amyl Nitrite.
IsoxsuprineThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Isoxsuprine.
IsradipineThe risk or severity of adverse effects can be increased when Isradipine is combined with Amyl Nitrite.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Amyl Nitrite.
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Amyl Nitrite.
LevodopaAmyl Nitrite may increase the orthostatic hypotensive activities of Levodopa.
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Amyl Nitrite.
LosartanThe risk or severity of adverse effects can be increased when Losartan is combined with Amyl Nitrite.
MannitolThe risk or severity of adverse effects can be increased when Mannitol is combined with Amyl Nitrite.
MecamylamineThe risk or severity of adverse effects can be increased when Mecamylamine is combined with Amyl Nitrite.
MethazolamideThe risk or severity of adverse effects can be increased when Methazolamide is combined with Amyl Nitrite.
MethohexitalMethohexital may increase the hypotensive activities of Amyl Nitrite.
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Amyl Nitrite.
MethyldopaThe risk or severity of adverse effects can be increased when Methyldopa is combined with Amyl Nitrite.
MethylphenobarbitalMethylphenobarbital may increase the hypotensive activities of Amyl Nitrite.
MetipranololThe risk or severity of adverse effects can be increased when Metipranolol is combined with Amyl Nitrite.
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Amyl Nitrite.
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Amyl Nitrite.
MinoxidilThe risk or severity of adverse effects can be increased when Minoxidil is combined with Amyl Nitrite.
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Amyl Nitrite.
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Amyl Nitrite.
NebivololThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Nebivolol.
NesiritideThe risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Nesiritide.
NicardipineThe risk or severity of adverse effects can be increased when Nicardipine is combined with Amyl Nitrite.
NicorandilNicorandil may increase the hypotensive activities of Amyl Nitrite.
NifedipineThe risk or severity of adverse effects can be increased when Nifedipine is combined with Amyl Nitrite.
NimodipineThe risk or severity of adverse effects can be increased when Nimodipine is combined with Amyl Nitrite.
NisoldipineThe risk or severity of adverse effects can be increased when Nisoldipine is combined with Amyl Nitrite.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Amyl Nitrite.
NitroglycerinThe risk or severity of adverse effects can be increased when Nitroglycerin is combined with Amyl Nitrite.
NitroprussideThe risk or severity of adverse effects can be increased when Nitroprusside is combined with Amyl Nitrite.
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Amyl Nitrite.
PapaverineThe risk or severity of adverse effects can be increased when Papaverine is combined with Amyl Nitrite.
PenbutololThe risk or severity of adverse effects can be increased when Penbutolol is combined with Amyl Nitrite.
PentobarbitalPentobarbital may increase the hypotensive activities of Amyl Nitrite.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Amyl Nitrite.
PhenobarbitalPhenobarbital may increase the hypotensive activities of Amyl Nitrite.
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Amyl Nitrite.
PrazosinThe risk or severity of adverse effects can be increased when Prazosin is combined with 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.
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Amyl Nitrite.
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Amyl Nitrite.
QuinaprilThe risk or severity of adverse effects can be increased when Quinapril is combined with Amyl Nitrite.
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Amyl Nitrite.
ReserpineThe risk or severity of adverse effects can be increased when Reserpine is combined with Amyl Nitrite.
RiociguatAmyl Nitrite may increase the hypotensive activities of Riociguat.
RiociguatThe risk or severity of adverse effects can be increased when Riociguat is combined with Amyl Nitrite.
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.
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Amyl Nitrite.
SpironolactoneThe risk or severity of adverse effects can be increased when Spironolactone is combined with Amyl Nitrite.
TadalafilTadalafil may increase the vasodilatory activities of Amyl Nitrite.
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Amyl Nitrite.
TerazosinThe risk or severity of adverse effects can be increased when Terazosin is combined with Amyl Nitrite.
ThiamylalThiamylal may increase the hypotensive activities of Amyl Nitrite.
ThiopentalThiopental may increase the hypotensive activities of Amyl Nitrite.
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Amyl Nitrite.
TizanidineThe risk or severity of adverse effects can be increased when Tizanidine is combined with Amyl Nitrite.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Amyl Nitrite.
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Amyl Nitrite.
TriamtereneThe risk or severity of adverse effects can be increased when Triamterene is combined with Amyl Nitrite.
UdenafilUdenafil 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.
VerapamilThe risk or severity of adverse effects can be increased when Verapamil is combined with 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