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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
Synthesis of purin-2-yl carboxylate from O6-methylguanosine.
2005
Design and evaluation of S-nitrosylated human serum albumin as a novel anticancer drug.
2008 Apr
Synthesis of alpha-oximinoketones under ultrasound irradiation.
2008 Apr
S-nitrosylated human serum albumin-mediated cytoprotective activity is enhanced by fatty acid binding.
2008 Dec 12
anti-Tricyclo-[4.2.1.1]deca-3,7-diene-9-endo,10-endo-diol.
2008 Nov 8
Aliphatic beta-nitro alcohols for non-enzymatic collagen cross-linking of scleral tissue.
2008 Sep
A facile access to [60]fullerene-fused delta-lactones: unexpected reaction pathway of benzenediazonium-2-carboxylates controlled by organic bases.
2009 Apr 7
Formation of diazoate intermediate upon nitrous acid and nitric oxide treatment of 2'-deoxyadenosine.
2009 Feb 1
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 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
Code System Code Type Description
NSC
7903
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
PRIMARY
DRUG BANK
DB01612
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
PRIMARY
MERCK INDEX
m6438
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
PRIMARY Merck Index
CAS
110-46-3
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-770-8
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
PRIMARY
PUBCHEM
8053
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
PRIMARY
FDA UNII
5N0U5TUC9Z
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
PRIMARY
HSDB
606
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
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NCI_THESAURUS
C87283
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
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MESH
C048958
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
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CHEBI
2691
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID9025455
Created by admin on Fri Dec 15 15:39:27 UTC 2023 , Edited by admin on Fri Dec 15 15:39:27 UTC 2023
PRIMARY