Isopropyl nitrite
Chemical compound
- None
- UK: Controlled Drug (Medicines Act 1968)
- US: Unscheduled (illegal under Crime Control Act of 1990)
- 2-propyl nitrite
- 541-42-4
Y
- 10929
- 10466 Y
- 2T3Y2PS0ZE
- DTXSID3052191
- Interactive image
- O=NOC(C)C
InChI
- InChI=1S/C3H7NO2/c1-3(2)6-4-5/h3H,1-2H3Y
- Key:SKRDXYBATCVEMS-UHFFFAOYSA-NY
The chemical compound isopropyl nitrite (or 2-propyl nitrite) is an alkyl nitrite made from isopropanol. It is a clear pale yellow oil that is insoluble in water.[1]
Applications
Isopropyl nitrite is one of the compounds used as poppers, an inhalant drug that induces a brief euphoria.
Safety
Isopropyl nitrite has been associated with eye maculopathy, visual impairment with central scotomata, bilateral foveal yellow spots, and inner segment/outer segment (IS/OS) junction disruption,[2] which may be reversible.[3]
References
- ^ Lide DR, ed. (2004). Handbook of Chemistry and Physics (85th ed.). CRC Press. ISBN 978-0-8493-0485-9.
- ^ Davies AJ, Kelly SP, Naylor SG, Bhatt PR, Mathews JP, Sahni J, et al. (November 2012). "Adverse ophthalmic reaction in poppers users: case series of 'poppers maculopathy'". Eye. 26 (11): 1479–1486. doi:10.1038/eye.2012.191. PMC 3496104. PMID 23079752.
- ^ Vignal-Clermont C, Audo I, Sahel JA, Paques M (October 2010). "Poppers-associated retinal toxicity". The New England Journal of Medicine. 363 (16): 1583–5. doi:10.1056/NEJMc1005118. PMID 20942681.
- v
- t
- e
- Nitroxyl anion (NO−; oxonitrate(1-), hyponitrite anion)
- Nitric oxide (NO⋅; nitrogen monoxide)
- Nitrosonium (NO+; nitrosyl cation)
| sGC |
|
|---|
(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
(inhibitors)
| NOS |
| ||||||||
|---|---|---|---|---|---|---|---|---|---|
| Arginase |
| ||||||||
| CAMK |
|
- Precursors: L-Arginine
- Nω-Hydroxy-L-arginine (NOHA)
- Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan)
- ETB receptor antagonists (e.g., bosentan)
- L-Type calcium channel blockers (e.g., 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
