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Details

Stereochemistry ACHIRAL
Molecular Formula C5H11NO2
Molecular Weight 117.1463
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOPENTYL NITRITE

SMILES

CC(C)CCON=O

InChI

InChIKey=OWFXIOWLTKNBAP-UHFFFAOYSA-N
InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3

HIDE SMILES / InChI
ISOPENTYL NITRITE (Amyl nitrite) is a chemical compound with an amyl group attached to the nitrite functional group. Amyl nitrite, in common with other alkyl nitrites, is a potent vasodilator; it expands blood vessels, resulting in lowering of the blood pressure. Alkyl nitrites are a source of nitric oxide, which signals for relaxation of the involuntary muscles. Physical effects include the 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 internal and external anal sphincter. There are no withdrawal symptoms. Overdose symptoms include nausea, vomiting, hypotension, hypoventilation, shortness of breath, and fainting. The effects set in very quickly, typically within a few seconds and disappear within a few minutes. Amyl nitrite may also intensify the experience of synesthesia. Amyl nitrite is employed medically to treat heart diseases as well as angina. Amyl nitrite is sometimes used as an antidote for cyanide poisoning. It can act as an oxidant, to induce the formation of methemoglobin. Methemoglobin, in turn, can sequester cyanide as cyanomethemoglobin.

Originator

Sources: Berichte der Deutschen Chemischen Gesellschaft, Volume23, Pages 2994

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMYL NITRITE

Approved Use

INDICATIONS AND USAGE: Amyl nitrite is indicated for the rapid relief of angina pectoris. Its effect appears within 30 seconds and lasts for approximately 3 to 5 minutes.
PubMed

PubMed

TitleDatePubMed
Inhibition of lipid peroxidation in synaptosomes and liposomes by nitrates and nitrites.
2002 Jul
Organic nitrites and NO: inhibition of lipid peroxidation and radical reactions.
2004 Feb
Nitrosation of sugar oximes: preparation of 2-glycosyl-1-hydroxydiazene-2-oxides.
2005 Dec 23
Synthesis of peroxynitrite using isoamyl nitrite and hydrogen peroxide in a homogeneous solvent system.
2006 Jul 15
New modular and efficient approach to 6-substituted pyridin-2-yl C-nucleosides.
2006 Sep 15
anti-Tricyclo-[4.2.1.1]deca-3,7-diene-9-endo,10-endo-diol.
2008 Nov 8
A facile access to [60]fullerene-fused delta-lactones: unexpected reaction pathway of benzenediazonium-2-carboxylates controlled by organic bases.
2009 Apr 7
Photolysis of n-butyl nitrite and isoamyl nitrite at 355 nm: a time-resolved Fourier transform infrared emission spectroscopy and ab initio study.
2009 May 7
Peroxynitrite modifies the structure and function of the extracellular matrix proteoglycan perlecan by reaction with both the protein core and the heparan sulfate chains.
2010 Jul 15
2,6-Dichloro-pyridine-3,5-dicarbonitrile.
2010 Sep 25
Patents

Sample Use Guides

Adults: 0.3 milliliter (1 ampul) taken by inhaling the vapor of amyl nitrite through the nose. Dose may be repeated within 1 to 5 minutes if pain is not relieved. If you still have chest pain after a total of 2 doses in a 10-minute period, contact your doctor or have someone take you to a hospital emergency room without delay.
Route of Administration: Respiratory
In Vitro Use Guide
Unknown
Name Type Language
ISOPENTYL NITRITE
Systematic Name English
3-METHYLBUTANOL NITRITE
Systematic Name English
ISOAMYL NITRITE
MI  
Systematic Name English
AMYL NITRITE [HSDB]
Common Name English
3-METHYLBUTYL NITRITE
Systematic Name English
NITROUS ACID, 3-METHYLBUTYL ESTER
Common Name English
ISOAMYL NITRITE [MI]
Common Name English
NITROUS ACID, ISOPENTYL ESTER
Common Name English
NSC-7903
Code English
ISOPENTYL ALCOHOL, NITRITE
Systematic Name English
AMYL NITRITE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
Code System Code Type Description
NSC
7903
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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DRUG BANK
DB01612
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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MERCK INDEX
m6438
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
PRIMARY Merck Index
CAS
110-46-3
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ECHA (EC/EINECS)
203-770-8
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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PUBCHEM
8053
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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FDA UNII
5N0U5TUC9Z
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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HSDB
606
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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NCI_THESAURUS
C87283
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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MESH
C048958
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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CHEBI
2691
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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EPA CompTox
DTXSID9025455
Created by admin on Fri Dec 15 15:39:27 GMT 2023 , Edited by admin on Fri Dec 15 15:39:27 GMT 2023
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