Cyclohexyl nitrite

Last updated
Cyclohexyl nitrite
Cyclohexyl nitrite.png
Cyclohexyl nitrite 3d structure.png
Clinical data
Other namesNitrous acid, cyclohexyl ester; N-Cyclohexyl nitrite; Cyclohexyl alcohol nitrite; C-hexyl nitrite; O-Nitrosocyclohexanol
ATC code
  • none
Identifiers
  • cyclohexyl nitrite
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C6H11NO2
Molar mass 129.159 g·mol−1
3D model (JSmol)
  • O=NOC1CCCCC1
  • InChI=1S/C6H11NO2/c8-7-9-6-4-2-1-3-5-6/h6H,1-5H2 Yes check.svgY
  • Key:NRCNZCLHYWKEDX-UHFFFAOYSA-N Yes check.svgY
   (verify)

Cyclohexyl nitrite is an organic compound, with formula C6H11NO2. [1] [2] It is the ester of cyclohexanol and nitrous acid, i.e. it is an alkyl nitrite. Like amyl nitrite and butyl nitrite, it acts as an antianginal due to vasodilation. The compound is colorless, volatile liquid.

Contents

Safety

Inhaling the cyclohexyl nitrite vapor can lead to headache and dangerously low blood pressure.

Recreational use

Since early 2020 cyclohexyl nitrite has become popular as a recreational drug called poppers, mostly labeled as Canadian formula in various online stores that offer purchase of the drug. When used as an inhalant the effects are described as - stimulating ejaculation and orgasm, relaxation of sphincter muscles during anal sex, therefore making this compound appealing to the gay community, although users describe the experience as not even close compared to other alkyl nitrites. [3]

Related Research Articles

<span class="mw-page-title-main">Amyl nitrite</span> Chemical compound

Amyl nitrite is a chemical compound with the formula C5H11ONO. A variety of isomers are known, but they all feature an amyl group attached to the nitrite functional group. The alkyl group is unreactive and the chemical and biological properties are mainly due to the nitrite group. 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 a psychoactive effect, which has led to its recreational use, with its smell being described as that of old socks or dirty feet. It is also referred to as banapple gas.

In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of −CnH2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula −CnH2n−1. Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula −CH3.

The nitrite ion has the chemical formula NO
2
. Nitrite is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also refers to organic compounds having the –ONO group, which are esters of nitrous acid.

<span class="mw-page-title-main">Amyl nitrate</span> Chemical compound

Amyl nitrate is the chemical compound with the formula CH3(CH2)4ONO2. This molecule consists of the 5-carbon amyl group attached to a nitrate functional group. It is the ester of amyl alcohol and nitric acid.

Thiazole, or 1,3-thiazole, is a heterocyclic compound that contains both sulfur and nitrogen. The term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular formula C3H3NS. The thiazole ring is notable as a component of the vitamin thiamine (B1).

<span class="mw-page-title-main">Butyl nitrite</span> Chemical compound

Butyl nitrite is the organic compound with the formula CH3(CH2)3ONO. It is an alkyl nitrite made from n-butanol. Butyl nitrite is used recreationally as poppers. Synonyms include 1-butyl nitrite, n-butyl nitrite and nitrous acid butyl ester.

The chemical compound ethyl nitrite is an alkyl nitrite with a chemical formula C2H5NO2. It may be prepared from ethanol.

<span class="mw-page-title-main">Methyl nitrite</span> Chemical compound

Methyl nitrite is an organic compound with the chemical formula CH
3
ONO
. It is a gas, and is the simplest alkyl nitrite.

<span class="mw-page-title-main">Isopropyl nitrite</span> Chemical compound

The chemical compound isopropyl nitrite is an alkyl nitrite made from isopropanol. It is a clear pale yellow oil that is insoluble in water.

Popper is a slang term given broadly to drugs of the chemical class called alkyl nitrites that are inhaled. They act on the body as vasodilaters. Most widely sold products include the original isoamyl nitrite, isopentyl nitrite, and isopropyl nitrite. Isobutyl nitrite is also widely used but is banned in the European Union. In some countries, poppers are labeled or packaged as room deodorizers, leather polish, nail polish remover, or videotape head cleaner to evade anti-drug laws.

<span class="mw-page-title-main">Pentyl group</span> Chemical compound

Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane.

Isobutyl nitrite, C4H9NO2, is an alkyl nitrite, an ester of isobutanol and nitrous acid. Its chemical structure is (CH3)2CH-CH2-ONO.

<span class="mw-page-title-main">Alkyl nitrites</span> Organic compounds of the form R–O–N=O

In organic chemistry, alkyl nitrites are a group of organic compounds based upon the molecular structure R−O−N=O, where R represents an alkyl group. Formally they are alkyl esters of nitrous acid. They are distinct from nitro compounds.

<span class="mw-page-title-main">Semustine</span> Chemical compound

Semustine is an alkylating nitrosourea compound used in chemotherapy treatment of various types of tumours. Due to its lipophilic property, semustine can cross the blood-brain barrier for the chemotherapy of brain tumours, where it interferes with DNA replication in the rapidly-dividing tumour cells. Semustine, just as lomustine, is administered orally. Evidence has been found that treatment with semustine can cause acute leukaemia as a delayed effect in very rare cases.

The molecular formula C6H11NO2 may refer to:

These drugs are known in the UK as controlled drug, because this is the term by which the act itself refers to them. In more general terms, however, many of these drugs are also controlled by the Medicines Act 1968, there are many other drugs which are controlled by the Medicines Act but not by the Misuse of Drugs Act, and some other drugs are controlled by other laws.

<span class="mw-page-title-main">Arylcyclohexylamine</span> Class of chemical compounds

Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

Pentyl nitrite is a chemical compound with the molecular formula, classified as an alkyl nitrite, used as an antihypertensive medicine. It is also used to treat cyanide poisoning.

<span class="mw-page-title-main">2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate</span> Chemical compound

2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate is an extremely toxic organophosphate nerve agent. It is the cyclohexyl methylphosphonate ester of ethyl acetoacetate. The compound has two isomers, the cis isomer and trans isomer, with the trans isomer being more toxic.

Hexyl nitrite has the formula C6H13NO2 and is a nitrite and more specifically, an alkyl nitrite. It is an ester of hexanol and nitrous acid. It has the structural formula of: CH3(CH2)5ONO The CAS Registry Number is 638-51-7 and the European Community number 680-102-5. It is REACH and TSCA registered. It is also known as nitrous acid, hexyl ester. It is the aliphatic analogue of cyclohexyl nitrite.

References

  1. "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2023-09-21.
  2. "J-GLOBAL. Cyclohexyl nitrite". Japan Science and Technology Agency. Retrieved 2023-09-21.
  3. Shapiro H, Buckle J (6 January 2016). "Nitrites". DrugWise.