Isobutyl nitrite

Isobutyl nitrite^[1]
Names
	Preferred IUPAC name 2-Methylpropyl nitrite
	Other names Isobutyl nitrite
Identifiers
CAS Number	542-56-3 ;
3D model ( JSmol)	Interactive image;
ChEBI	CHEBI:46643 ;
ChemSpider	10493 ;
ECHA InfoCard	100.008.018
PubChem CID	10958;
UNII	GW9WAB6QOM ;
CompTox Dashboard (EPA)	DTXSID3020750 ;
	InChI InChI=1S/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3 Key: APNSGVMLAYLYCT-UHFFFAOYSA-N ; InChI=1/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3 Key: APNSGVMLAYLYCT-UHFFFAOYAF;
	SMILES O=NOCC(C)C;
Properties
Chemical formula	C4H9NO2
Molar mass	103.11976
Appearance	Colorless liquid
Odor	Almond-like
Density	0.87 g/mL
Boiling point	67 °C (153 °F; 340 K)
Solubility in water	Slightly soluble
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly flammable
Legal status	BR: Class C1 (Other controlled substances);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Isobutyl nitrite, C₄H₉NO₂, is an

CH₃)₂CH-CH₂-ONO

.

Isobutyl nitrite is a pungent colorless liquid. It acts as a

recreational drug, poppers

.

Applications

Isobutyl nitrite is one of the compounds used as poppers, an inhalant drug that induces a brief euphoria. Also, it is used as part of the antidote package for cyanide poisoning.^{[medical citation needed]}

Safety

May cause headaches, dizziness and fainting. Isobutyl nitrite is poisonous to people with glucose-6-phosphate dehydrogenase deficiency.^[4]

References

^ Merck Index, 11th Edition, 5032.
^ CDC - NIOSH Pocket Guide to Chemical Hazards
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
PMID 26417175
.

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Nitric oxide signaling modulators
Forms

Nitroxyl anion (NO⁻; oxonitrate(1-), hyponitrite anion)

Nitric oxide (NO^⋅; nitrogen monoxide)

Nitrosonium (NO⁺; nitrosyl cation)

sGC

Activators/stimulators: Ataciguat

BAY 41-2272

BAY 41-8543

BAY 60-4552

BI-703704

Cinaciguat (BAY 58-2667)

GSK-2181236A

Praliciguat

Riociguat

Vericiguat

Inhibitors: ODQ

NO donors
(prodrugs
)

Nitrates: Diethylene glycol dinitrate (DEGDN)

Erythritol tetranitrate (ETN)

Ethylene glycol dinitrate (EGDN; nitroglycol)

Isosorbide mononitrate (ISMN)

Isosorbide dinitrate (ISDN)

Itramin tosilate

Mannitol hexanitrate

Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)

NCX-466

NCX-2216

NCX-4016

NCX 4040

NCX-4215

Nicorandil

Nipradilol (K-351)

Nitrate (NO⁻
₃)

Nitroatorvastatin (NCX-6560)

Nitroflurbiprofen (HCT-1026)

Nitrofluvastatin

Nitroglycerin (glyceryl trinitrate (GTN))

Nitropravastatin (NCX-6550)

Pentaerithrityl tetranitrate (PETN)

Propatylnitrate

Propylene glycol dinitrate (PGDN)

Sodium trioxodinitrate (Angeli's salt)

Tenitramine

Trolnitrate

Nitroso compounds/nitrites: Nitrite (NO⁻
₂); O-Nitroso compounds (alkyl nitrites): Amyl nitrite (isoamyl nitrite, isopentyl nitrite)

Cyclohexyl nitrite

Ethyl nitrite

Hexyl nitrite

Isobutyl nitrite (2-methylpropyl nitrite)

Isopropyl nitrite

Methyl nitrite

n-Butyl nitrite

Pentyl nitrite

tert-Butyl nitrite; S-Nitroso compounds (thionitrites): LA810

S-Nitrosoalbumin (SNALB)

S-Nitrosated AR545C

S-Nitroso-N-acetylcysteine (SNAC)

S-Nitroso-N-acetylpenicillamine (SNAP)

S-Nitroso-N-valerylpenicillamine (SNVP)

S-Nitrosocaptopril (SNO-Cap)

S-Nitrosocysteine (SNC, CysNO, SNO-Cys)

S-Nitrosodiclofenac

S-Nitrosoglutathione (GSNO, SNOG)

SNO-t-PA

SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A

Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black salt

Roussin's red salt

Sodium nitroprusside (SNP)

NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO)

Diethylenetriamine/NO (DETA/NO)

GLO/NO

JS-K

Methylamine hexamethylene methylamine/NO (MAHMA/NO)

PROLI/NO

Spermine/NO (SPER/NO)

V-PYRRO/NO

Heterocyclic compounds: Furoxans: Furoxan

REC15/2739; Sydnonimines: Feprosidnine

Linsidomine (SIN-1)

Molsidomine (SIN-10)

Sydnonimine

Unsorted: Cimlanod

FK-409

FR144220

FR146881

N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide

Enzyme
(inhibitors)
NOS
nNOS

3-Bromo-7-nitroindazole

3-Chloroindazole

3-Chloro-5-nitroindazole

5-Nitroindazole

6-Nitroindazole

7-Nitroindazole

A-84643

Aminoguanidine (pimagedine)

ARL-17477

Indazole

N⁵-(1-Iminoethyl)-L-ornithine (L-NIO)

N^ω-Methyl-L-arginine (L-NMA)

N^ω-Propyl-L-arginine (L-NPA)

Nitroarginine (NNA, NOARG)

Pentamidine isethionate

TRIM

iNOS

1-Amino-2-hydroxyguanidine

2-Ethylaminoguanidine

2-Iminopiperidine

1400W

AEITU

Aminoguanidine (pimagedine)

AMT

AR-C 102222

BYK-191023

Canavanine

Cindunistat (SD-6010)

EITU

IPTU

MITU

N⁵-(1-Iminoethyl)-L-ornithine (L-NIO)

N⁶-(1-Iminoethyl)-L-lysine (L-NIL)

N^ω-Methyl-L-arginine (L-NMA)

Ronopterin (VAS-203)

TRIM

eNOS

Aminoguanidine (pimagedine)

N⁵-(1-Iminoethyl)-L-ornithine (L-NIO)

N^ω-Methyl-L-arginine (L-NMA)

Nitroarginine (NNA, NOARG)

Unsorted

Asymmetric dimethylarginine (ADMA)

CKD-712

Guanidinoethyldisulfide (GED)

GW-273629

Indospicine

KD-7040

Nitroarginine methyl ester (NAME)

NCX-456

NXN-462

ONO-1714

VAS-2381

Arginase

ABH

N^ω-Hydroxy-L-arginine (NOHA)

chlorogenic acid

ginseng

epicatechin

ornithine

norvaline

lysine

alpha aminoacids

CAMK

Calmidazolium

W-7

Others

Precursors: L-Arginine

N^ω-Hydroxy-L-arginine (NOHA)

Cofactors: NADPH

FAD

FMN

Heme

BH₄

CaM

O₂

Ca²⁺

Indirect/downstream NO modulators:
AT-II receptor antagonists (e.g., captopril, losartan
)

ET_B receptor antagonists (e.g., bosentan)

dihydropyridines: nifedipine
)

Nebivolol (beta blocker)

PDE5 inhibitors (e.g., sildenafil)

non-selective PDE inhibitors (e.g., caffeine)

PDE9 inhibitors (e.g., paraxanthine)

cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)

Statins (e.g., simvastatin)

See also: Receptor/signaling modulators

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[1] Merck Index, 11th Edition, 5032.

[2] CDC - NIOSH Pocket Guide to Chemical Hazards

[3] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[4] PMID 26417175
.

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