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. Isopropyl nitrite has largely replaced isobutyl nitrite in poppers.
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
