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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

Molecular Formula C5H11NO2
Molecular Weight 117.1463
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMYL NITRITE

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Record UNII
5N0U5TUC9Z
Record Status Validated (UNII)
Record Version