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
Synonyms
  • 1-nitropentane
  • n-Amyl nitrite
  • n-pentyl nitrite
  • Nitramyl
  • pentyl nitrite
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amyl Nitrite Vitrellae Bpc Liq 0.33 Ml/capLiquid0.33 mlRespiratory (inhalation)Shire Pharma Canada Ulc1997-04-012001-10-01Canada
Amylnitrite Glass Cap 5minLiquid.3 mlRespiratory (inhalation)Allen & Hanburys A Glaxo Canada Ltd. Co.1951-12-311999-08-06Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Amyl NitriteAmyl Nitrite (0.3 g/0.3mL)InhalantRespiratory (inhalation)James Alexander Corporation1979-02-07Not applicableUs
International/Other Brands
Aspiral / Vaporole
Categories
UNII
H2HUX79FYK
CAS number
8017-89-8
Weight
Average: 117.1463
Monoisotopic: 117.078978601
Chemical Formula
C5H11NO2
InChI Key
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

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. 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.

TargetActionsOrganism
AAtrial natriuretic peptide receptor 1
agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Amyl Nitrite.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen 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.
AmifostineThe risk or severity of adverse effects can be increased when Amifostine is combined with Amyl Nitrite.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Amyl Nitrite.
AmiodaroneThe risk or severity of adverse effects can be increased when Amiodarone 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.
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Amyl Nitrite.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015550
KEGG Drug
D00517
KEGG Compound
C07457
PubChem Compound
10026
PubChem Substance
46507839
ChemSpider
9632
ChEBI
55344
ChEMBL
CHEMBL3188202
PharmGKB
PA164750570
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Amyl_nitrite
ATC Codes
V03AB22 — Amyl nitrite

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableRecruitingDiagnosticAchalasia / Swallowing Disorders1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • James Alexander Corp.
  • Keystone Pharmaceuticals Inc.
  • X-Gen Pharmaceuticals
Dosage forms
FormRouteStrength
InhalantRespiratory (inhalation)0.3 g/0.3mL
LiquidRespiratory (inhalation)0.33 ml
LiquidRespiratory (inhalation).3 ml
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (9.66 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as organic o-nitroso compounds. These are organic compounds containing a n-nitroso group -ON=O.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Organic nitroso compounds
Direct Parent
Organic O-nitroso compounds
Alternative Parents
Alkyl nitrites / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Organic o-nitroso compound / Alkyl nitrite / Organic nitrite / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
nitrite esters (CHEBI:55344)

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 ...
Gene Name
NPR1
Uniprot ID
P16066
Uniprot Name
Atrial natriuretic peptide receptor 1
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
Uniprot Name
Aldehyde dehydrogenase, mitochondrial
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]

Drug created on August 29, 2007 14:03 / Updated on November 02, 2018 05:04