865:
346:
38:
965:, characterized by a blue-brown discoloration under the skin which could be mistaken for cyanosis. Treatment with oxygen and intravenous methylene blue frustrates visual confirmation further as methylene blue itself is, as its name suggests, a blue dye; the patient's changes in different shades of blue notwithstanding, it is an effective antidote by way of catalyzing the production of the enzyme responsible for reducing the methemoglobin in the blood back to hemoglobin.
47:
948:. Amyl nitrite, when given as a medication for patients with angina, can also be administered as an ampule. The ampule is put in a gauze pad and then inhaled by the patient during an angina attack and repeated every fifteen minutes. However, oral dosing of amyl nitrite is ineffective due to poor absorption and extensive hepatic metabolism. Amyl nitrite has been widely replaced by
960:
Although there are case reports of life-threatening toxicity involving unusually large amounts, typical inhaled doses of amyl nitrite are considered relatively safe. However, liquid amyl nitrite is highly toxic when ingested because of the unsafely high concentration it causes in blood. Regardless of
968:
The discoloration does mean that regular near-infrared–based pulse oximetry becomes useless. More fundamentally, blood gas analysis on the whole has limited effectiveness, as the increased methemoglobin level increases the oxygen binding affinity of regular hemoglobin. Therefore, the measurement of
772:
to a cooled mixture of an aqueous sodium nitrite solution and an alcohol. The intermediately-formed stoichiometric mixture of nitrogen dioxide and nitric oxide then converts the alcohol to the alkyl nitrite, which, due to its low density, will form an upper layer that can be easily
961:
the form or route of administration, acute toxicity principally results when the nitrite oxidizes a significant proportion of hemoglobin in the blood without oxygen, forming methemoglobin, which cannot carry oxygen. Severe poisoning cases will progress to
987:" (1974–1975) features amyl nitrite inhaled by the antagonist Hayden Danziger – played by Robert Vaughn – to help him feign a heart attack for his alibi. However, the episode consistently refers to the substance incorrectly as amyl nitrate.
647:, colloquially called a "come down"; amyl nitrite is sometimes used to combat these negative after-effects. This effect, combined with its dissociative effects, has led to its use as a recreational drug
892:
and provoke obstruction of blood flow towards the aorta from the ventricle by increasing the pressure gradient, thereby causing left ventricular outflow obstruction. Alkyl nitrites are a source of
2502:
554:
effect, which has led to its recreational use, with its smell being described as that of old socks or dirty feet. It was first documented in 1844 and came into medical use in 1867.
80:
900:. Physical effects include decrease in blood pressure, headache, flushing of the face, increased heart rate, dizziness, and relaxation of involuntary muscles, especially the
768:. Synthesis of alkyl nitrites is, in general, straightforward and can be accomplished in home laboratories. A common procedure includes the dropwise addition of concentrated
1462:
Cornforth J, Kumar A, Stuart AS (1987). "Synthesis of substituted dibenzophospholes. Part 6. Preparation of symmetrical and non-symmetrical quaterphenyl intermediates".
1509:
2495:
542:
functional group. The alkyl group (the amyl in this case) is unreactive and the chemical and biological properties are mainly due to the nitrite group. Like other
888:. Amyl nitrite may be used during cardiovascular stress testing in patients with suspected hypertrophic cardiomyopathy to cause vasodilation and thereby reduce
460:
3635:
2488:
944:. 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
1024:, taking about two dozen ampules of it with him and usually justifying its usage by him and Dr. Gonzo to other people around them by claiming it's for
1663:
1345:
2446:
1549:
1619:
Nutt D, King LA, Saulsbury W, Blakemore C (March 2007). "Development of a rational scale to assess the harm of drugs of potential misuse".
864:
3264:
1813:
3690:
1044:
2949:
1328:
1097:
480:
3115:
3302:
2628:
2222:
2919:
2345:
163:
110:
3024:
969:
actual ratios and levels of methemoglobin and hemoglobin must accompany any blood gas partial pressure sample in these cases.
3704:
1355:
1016:
639:, the euphoric state intensifies and is prolonged. Once some stimulative drugs wear off, a common side effect is a period of
1518:
3386:
3254:
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2778:
265:
1293:
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3451:
2924:
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2463:
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325:
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3342:
3209:
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2674:
2562:
2398:
2255:
1947:
1540:
145:
3481:
3355:
3272:
2914:
3169:
1710:
3461:
3292:
3159:
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3249:
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2451:
2175:
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909:
905:
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564:
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3009:
3718:
3422:
3368:
3231:
3218:
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2679:
2425:
2391:
853:
631:
drug that induces a brief euphoric state, and when combined with other intoxicant stimulant drugs such as
3337:
2939:
2909:
597:
which had better efficacy, and the use of amyl nitrite has been found to be ineffective and unscientific
3832:
3812:
3645:
3327:
3142:
2929:
2281:
2193:
1004:
842:
617:
3282:
2986:
2934:
2758:
2753:
1275:
3567:
3164:
2904:
2773:
2763:
1172:
Vale JA (2001). "Cyanide
Antidotes: from Amyl Nitrite to Hydroxocobalamin – Which Antidote is Best?".
3179:
3174:
3004:
2991:
2944:
2768:
2694:
2684:
1869:
1846:
1770:
1174:
416:
3655:
3585:
2125:
996:
834:
745:
341:
180:
2603:
1435:
Smith WB, Ho OC (1990). "Application of the isoamyl nitrite-diiodomethane route to aryl iodides".
1236:"Does amyl nitrite have a role in the management of pre-hospital mass casualty cyanide poisoning?"
1133:"The effects of nitroglycerin and amyl nitrite on arteriolar and venous tone in the human forearm"
3817:
3322:
3307:
3085:
3065:
3034:
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1644:
1011:
984:
826:
133:
3590:
3381:
3312:
3060:
3039:
1572:"Methylene blue: a treatment for severe methaemoglobinaemia secondary to misuse of amyl nitrite"
3466:
3199:
2593:
2573:
3501:
3496:
3110:
3105:
3029:
2863:
2724:
2719:
2714:
2709:
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2185:
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2140:
1636:
1601:
1545:
1415:
1387:
1351:
1324:
1257:
1216:
1154:
1093:
1087:
962:
729:
has a similar structure and similar uses (also called 'poppers') but with worse side-effects.
726:
640:
574:
551:
519:
3491:
3486:
3476:
3456:
3189:
2704:
314:
3537:
3131:
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3014:
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2372:
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1628:
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1316:
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3396:
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3019:
2783:
2430:
2385:
2002:
1535:
933:
913:
568:
550:, which is the basis of its use as a prescription medicine. As an inhalant, it also has a
345:
254:
37:
189:
1774:
3745:
3404:
3297:
3194:
2894:
2881:
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2514:
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2320:
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2215:
2129:
1992:
1835:
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1320:
897:
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601:
1632:
46:
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3435:
3244:
2873:
2853:
2848:
2833:
2350:
2116:
2010:
1927:
949:
845:
769:
612:('Freon-12'), an industrial chemical universally banned in 1996 due to damage to the
586:
582:
543:
437:
2480:
3763:
3739:
3070:
2538:
2525:
2511:
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1919:
1826:
1648:
991:
901:
893:
881:
781:
749:
722:
673:
93:
88:
20:
1000:
features a character named Amyl
Nitrate (a misspelled reference to amyl nitrite).
1485:
Cadogan JI, Roy DA, Smith DM (1966). "An alternative to the
Sandmeyer reaction".
1252:
1235:
780:
Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the
214:
3776:
3547:
3471:
3080:
3075:
2960:
2801:
2699:
2543:
2340:
2311:
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1982:
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29:
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3694:
3557:
3552:
2613:
2020:
1977:
1962:
1932:
1879:
1149:
1132:
1021:
1020:
sees amyl nitrite as one of the many drugs Raoul Duke packs for the trip to
889:
849:
815:
1640:
1605:
1261:
1220:
1045:"Amyl Nitrite (Inhalation Route) Description and Brand Names - Mayo Clinic"
3769:
cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
1158:
683:
group, and the resulting amyl nitrite would have the structural formula CH
3756:
3712:
3698:
3613:
3515:
3204:
3095:
2642:
2533:
2250:
2088:
2030:
2015:
1967:
1957:
1884:
1859:
1822:
1587:
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1471:
941:
917:
628:
621:
225:
1448:
1120:. New Hyde Park, NY.: Medical Examination Publishing Co. pp. 48–50.
234:
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2999:
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2739:
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200:
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3125:
2412:
1025:
925:
921:
677:
665:
535:
1791:
1737:"Amyl and The Sniffers: 'It's just charmingly violent powerful fun'"
718:
ONO, which may be more specifically referred to as isoamyl nitrite.
825:
Amyl nitrites are also useful as reagents in a modification of the
294:
1972:
863:
830:
819:
680:
415:
406:
305:
1517:(1st ed.). San Francisco California: PHARMEX. Archived from
3650:
3577:
3151:
702:
A common form of amyl nitrite is the isomer with the formula (CH
636:
285:
127:
2484:
1795:
139:
868:
An early container of amyl nitrite, Hunterian Museum, Glasgow
534:
ONO. A variety of isomers are known, but they all feature an
1069:"Drugs - Amyl, Butyl or Isobutyl Nitrite, Nitrates, Poppers"
330:
123:: Unscheduled (unauthorized sale and purchase illegal)
1684:
1007:
reference recreational use of amyl nitrite in their name.
563:
Amyl nitrite was historically employed medically to treat
119:
1691:. UK National Poisons Information Service. December 2018
593:
as cyanomethemoglobin. However, it has been replaced by
1118:
The
Handbook of Overdose and Detoxification Emergencies
505:
2534:
Nitroxyl anion (NO; oxonitrate(1-), hyponitrite anion)
1570:
Modarai B, Kapadia YK, Kerins M, Terris J (May 2002).
1464:
Journal of the
Chemical Society, Perkin Transactions 1
829:. The reaction of the alkyl nitrite with an aromatic
732:
Amyl nitrite is sometimes referred to colloquially as
668:. In older literature, the common non-systematic name
608:
in industrial and household applications. It replaced
1508:
Nickerson M, Parker JO, Lowry TP, Swenson EW (1979).
814:
Amyl nitrite, like other alkyl nitrites, reacts with
3603:
3576:
3514:
3444:
3395:
3263:
3150:
3141:
3124:
3025:
Methylamine hexamethylene methylamine/NO (MAHMA/NO)
2641:
2561:
2552:
2524:
2411:
2358:
2310:
2280:
2249:
2231:
2184:
2161:
2154:
2115:
2097:
2079:
2068:
2044:
2001:
1941:
1918:
1893:
1868:
1845:
1834:
573:Amyl nitrite was sometimes used as an antidote for
446:
436:
426:
404:
391:
361:
356:
324:
304:
284:
264:
244:
224:
199:
179:
154:
109:
104:
79:
58:
53:
1111:
1109:
488:InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3
2839:Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
1761:Kjonaas RA (1996). "Amyl: A Misunderstood Word".
1411:"(2S)-(−)-3-exo-(Morpholino)isoborneol ((−)-MIB)"
725:has very different properties. At the same time,
546:, amyl nitrite is bioactive in mammals, being a
213:
2700:Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
1565:
1563:
1561:
744:Alkyl nitrites are prepared by the reaction of
188:
1409:Chen YK, Jeon SJ, Walsh PJ, Nugent WA (2005).
1347:The A-Z Encyclopedia of Alcohol and Drug Abuse
852:is the solvent of choice for the synthesis of
3116:N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
2675:Ethylene glycol dinitrate (EGDN; nitroglycol)
2496:
1807:
841:atom from the solvent. For the synthesis of
8:
664:The term "amyl nitrite" encompasses several
28:
1116:Giannini AJ, Slaby AE, Giannini MC (1982).
3147:
3138:
2558:
2503:
2489:
2481:
2158:
2076:
1842:
1814:
1800:
1792:
1679:
1677:
1487:Journal of the Chemical Society C: Organic
344:
253:
2859:Isobutyl nitrite (2-methylpropyl nitrite)
2769:Nitroglycerin (glyceryl trinitrate (GTN))
1711:"Episode review: Columbo Troubled Waters"
1595:
1251:
1210:
1148:
699:ONO, also referred to as n-amyl nitrite.
620:cleaner. Trace amounts are added to some
273:
146:(illegal under Crime Control Act of 1990)
1787:Editorial on the use of the word "amyl".
1311:Cantrell F (2014). "Nitrite Inhalants".
452:Slightly soluble mg/mL (20 °C)
70:Pentyl alcohol nitrite (ambiguous),
2935:S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
2925:S-Nitroso-N-valerylpenicillamine (SNVP)
1131:Mason DT, Braunwald E (November 1965).
1036:
485:
465:
340:
233:
168:
2920:S-Nitroso-N-acetylpenicillamine (SNAP)
2794:Sodium trioxodinitrate (Angeli's salt)
1511:Isobutyl Nitrite and Related Compounds
1092:. John Wiley & Sons. p. XXX.
896:, which signals for relaxation of the
27:
627:It is also used recreationally as an
313:
7:
3755:non-selective PDE inhibitors (e.g.,
2539:Nitric oxide (NO; nitrogen monoxide)
1662:O'Malley MF, O'Malley R (May 2020).
1300:. U.S. National Library of Medicine.
1294:"Amyl Nitrite Use and Manufacturing"
837:aromatic species, this then frees a
833:in a halogenated solvent produces a
134:Controlled Drug (Medicines Act 1968)
92:
2779:Pentaerithrityl tetranitrate (PETN)
2665:Diethylene glycol dinitrate (DEGDN)
952:for the treatment of acute angina.
872:Amyl nitrite, in common with other
293:
204:
3684:Indirect/downstream NO modulators:
3452:Asymmetric dimethylarginine (ADMA)
1350:. Brown Walker Press. p. 94.
1321:10.1016/b978-0-12-386454-3.00042-7
1193:Hall AH, Saiers J, Baud F (2009).
14:
3482:Nitroarginine methyl ester (NAME)
2945:S-Nitrosoglutathione (GSNO, SNOG)
2915:S-Nitroso-N-acetylcysteine (SNAC)
2789:Propylene glycol dinitrate (PGDN)
2544:Nitrosonium (NO; nitrosyl cation)
1437:The Journal of Organic Chemistry
379:
373:
45:
36:
3010:Diethylenetriamine/NO (DETA/NO)
1234:Lavon O, Bentur Y (July 2010).
1086:Fischer J, Ganellin CR (2006).
884:, resulting in lowering of the
493:Key:OWFXIOWLTKNBAP-UHFFFAOYSA-N
3210:N-(1-Iminoethyl)-L-ornithine (
1315:. Elsevier. pp. 530–531.
1017:Fear and Loathing in Las Vegas
577:. It was thought to act as an
382:
367:
75:(ambiguous, colloquial, slang)
1:
3793:Receptor/signaling modulators
3462:Guanidinoethyldisulfide (GED)
2680:Isosorbide mononitrate (ISMN)
2670:Erythritol tetranitrate (ETN)
1763:Journal of Chemical Education
1633:10.1016/S0140-6736(07)60464-4
1282:. Royal Society of Chemistry.
1089:Analogue-based Drug Discovery
581:, to induce the formation of
2930:S-Nitrosocaptopril (SNO-Cap)
2759:Nitroflurbiprofen (HCT-1026)
2754:Nitroatorvastatin (NCX-6560)
1670:. 2023 Merck & Co., Inc.
1253:10.3109/15563650.2010.505573
676:, where the amyl group is a
68:3-methyl-1-nitrosooxybutane,
3405:Aminoguanidine (pimagedine)
3298:Aminoguanidine (pimagedine)
3195:Aminoguanidine (pimagedine)
2959:N-Nitroso compounds (e.g.,
2774:Nitropravastatin (NCX-6550)
2685:Isosorbide dinitrate (ISDN)
777:from the reaction mixture.
756:ROH + HONO → RONO + H
648:
3854:
3691:AT-II receptor antagonists
3436:Nitroarginine (NNA, NOARG)
3273:1-Amino-2-hydroxyguanidine
3245:Nitroarginine (NNA, NOARG)
2992:Sodium nitroprusside (SNP)
1576:Emergency Medicine Journal
1397:, vol. 2, p. 108
1313:Encyclopedia of Toxicology
600:Amyl nitrite is used as a
357:Chemical and physical data
18:
3786:
2441:
2399:Prednisolone/promethazine
2380:Methylthioninium chloride
1541:The Man Who Tasted Shapes
1276:"Dichlorodifluoromethane"
1212:10.1080/10408440802304944
1195:"Which cyanide antidote?"
501:
476:
456:
159:
44:
35:
3170:3-Chloro-5-nitroindazole
3005:Diethylamine/NO (DEA/NO)
2977:Metal nitrosyl complexes
2905:S-Nitrosoalbumin (SNALB)
2599:Cinaciguat (BAY 58-2667)
760:O, where R = alkyl group
442:99 °C (210 °F)
19:Not to be confused with
3762:PDE9 inhibitors (e.g.,
3250:Pentamidine isethionate
3160:3-Bromo-7-nitroindazole
3047:Heterocyclic compounds:
2571:Activators/stimulators:
1150:10.1161/01.cir.32.5.755
910:external anal sphincter
764:The reaction is called
740:Synthesis and reactions
672:was often used for the
610:dichlorodifluoromethane
171:(3-methylbutyl) nitrite
3719:L-Type calcium channel
2392:Potassium permanganate
2048:neuromuscular blockade
869:
589:in turn can sequester
538:group attached to the
3323:Cindunistat (SD-6010)
3278:2-Ethylaminoguanidine
3035:Spermine/NO (SPER/NO)
2832:O-Nitroso compounds (
2194:4-Dimethylaminophenol
1005:Amyl and the Sniffers
867:
860:Physiological effects
618:printed circuit board
3709:receptor antagonists
3382:Ronopterin (VAS-203)
3081:Molsidomine (SIN-10)
3002:(diazeniumdiolates):
2982:Roussin's black salt
2695:Mannitol hexanitrate
2282:Paracetamol toxicity
2126:direct Xa inhibitors
1847:Alcohol intoxication
1588:10.1136/emj.19.3.270
1495:10.1039/J39660001249
1472:10.1039/P19870000859
1344:Nordegren T (2002).
1240:Clin Toxicol (Phila)
721:The similarly named
678:linear or normal (n)
3076:Linsidomine (SIN-1)
2973:Nitrosyl compounds:
2940:S-Nitrosodiclofenac
2910:S-Nitrosated AR545C
2895:S-Nitroso compounds
1775:1996JChEd..73.1127K
1717:. 29 September 2018
1664:"Volatile Nitrites"
1627:(9566): 1047–1053.
1449:10.1021/jo00295a056
938:shortness of breath
898:involuntary muscles
448:Solubility in water
32:
2987:Roussin's red salt
2844:Cyclohexyl nitrite
2735:Nipradilol (K-351)
2468:Never to phase III
2265:Primary alcohols:
2223:Sodium thiosulfate
2107:Digoxin immune fab
1783:10.1021/ed073p1127
1049:www.mayoclinic.org
1012:Hunter S. Thompson
973:In popular culture
870:
827:Sandmeyer reaction
144: Unscheduled
64:Isopentyl nitrite,
3800:
3799:
3625:
3616:
3599:
3598:
3532:
3510:
3509:
3430:
3426:
3417:
3413:
3410:N-(1-Iminoethyl)-
3376:
3372:
3363:
3359:
3356:N-(1-Iminoethyl)-
3350:
3346:
3343:N-(1-Iminoethyl)-
3283:2-Iminopiperidine
3239:
3235:
3226:
3222:
3213:
3135:
2864:Isopropyl nitrite
2810:Nitroso compounds
2652:
2637:
2636:
2478:
2477:
2407:
2406:
2241:Calcium gluconate
2233:Hydrofluoric acid
2186:Cyanide poisoning
2163:Arsenic poisoning
2150:
2149:
2064:
2063:
1715:Columbophile blog
1551:978-0-262-53255-6
1416:Organic Syntheses
1395:Collected Volumes
1388:Organic Syntheses
1383:"n-Butyl Nitrite"
963:methemoglobinemia
920:symptoms include
848:is used, whereas
796:ONO + NaOH → C
727:isopropyl nitrite
575:cyanide poisoning
520:chemical compound
513:
512:
417:Interactive image
326:CompTox Dashboard
143:
131:
122:
16:Chemical compound
3845:
3828:Muscle relaxants
3726:dihydropyridines
3626:-arginine (NOHA)
3623:
3614:
3568:alpha aminoacids
3538:chlorogenic acid
3533:-arginine (NOHA)
3530:
3428:
3424:
3415:
3411:
3374:
3370:
3361:
3357:
3348:
3344:
3237:
3233:
3224:
3220:
3211:
3165:3-Chloroindazole
3148:
3139:
3129:
2827:
2826:
2764:Nitrofluvastatin
2748:
2747:
2690:Itramin tosilate
2646:
2559:
2505:
2498:
2491:
2482:
2373:Potassium iodide
2199:Hydroxocobalamin
2159:
2099:Digoxin toxicity
2077:
1843:
1816:
1809:
1802:
1793:
1786:
1748:
1747:
1745:
1744:
1733:
1727:
1726:
1724:
1722:
1707:
1701:
1700:
1698:
1696:
1681:
1672:
1671:
1659:
1653:
1652:
1616:
1610:
1609:
1599:
1567:
1556:
1555:
1532:
1526:
1525:
1523:
1516:
1505:
1499:
1498:
1482:
1476:
1475:
1459:
1453:
1452:
1443:(8): 2543–2545.
1432:
1426:
1424:
1406:
1400:
1398:
1391:
1375:
1369:
1368:
1366:
1364:
1341:
1335:
1334:
1308:
1302:
1301:
1290:
1284:
1283:
1272:
1266:
1265:
1255:
1231:
1225:
1224:
1214:
1199:Crit Rev Toxicol
1190:
1184:
1183:
1169:
1163:
1162:
1152:
1128:
1122:
1121:
1113:
1104:
1103:
1083:
1077:
1076:
1065:
1059:
1058:
1056:
1055:
1041:
983:episode titled "
654:
595:hydroxocobalamin
509:
508:
419:
399:
384:
381:
375:
369:
349:
348:
334:
332:
317:
297:
277:
257:
237:
217:
207:
206:
192:
141:
138:
129:
126:
121:
118:
96:
62:Isoamyl nitrite,
49:
40:
33:
31:
3853:
3852:
3848:
3847:
3846:
3844:
3843:
3842:
3803:
3802:
3801:
3796:
3782:
3746:PDE5 inhibitors
3708:
3672:
3659:
3595:
3572:
3506:
3440:
3391:
3259:
3185:7-Nitroindazole
3180:6-Nitroindazole
3175:5-Nitroindazole
3128:
3120:
2897:(thionitrites):
2825:
2822:
2821:
2820:
2784:Propatylnitrate
2746:
2743:
2742:
2741:
2645:
2633:
2548:
2520:
2509:
2479:
2474:
2473:
2458:Clinical trials
2437:
2431:Syrup of ipecac
2403:
2386:oxidizing agent
2354:
2306:
2285:(Acetaminophen)
2284:
2276:
2257:
2256:Ethylene glycol
2254:
2245:
2227:
2180:
2146:
2111:
2093:
2071:
2060:
2046:
2040:
2003:Opioid overdose
1997:
1949:
1948:Organophosphate
1946:
1937:
1914:
1896:
1889:
1871:
1864:
1837:
1830:
1820:
1790:
1760:
1756:
1754:Further reading
1751:
1742:
1740:
1735:
1734:
1730:
1720:
1718:
1709:
1708:
1704:
1694:
1692:
1683:
1682:
1675:
1661:
1660:
1656:
1618:
1617:
1613:
1569:
1568:
1559:
1552:
1534:
1533:
1529:
1521:
1514:
1507:
1506:
1502:
1484:
1483:
1479:
1461:
1460:
1456:
1434:
1433:
1429:
1408:
1407:
1403:
1393:
1377:
1376:
1372:
1362:
1360:
1358:
1343:
1342:
1338:
1331:
1310:
1309:
1305:
1292:
1291:
1287:
1274:
1273:
1269:
1233:
1232:
1228:
1192:
1191:
1187:
1171:
1170:
1166:
1130:
1129:
1125:
1115:
1114:
1107:
1100:
1085:
1084:
1080:
1067:
1066:
1062:
1053:
1051:
1043:
1042:
1038:
1034:
985:Troubled Waters
975:
958:
934:hypoventilation
912:. There are no
862:
809:
803:
799:
795:
791:
782:isoamyl alcohol
759:
742:
717:
713:
709:
705:
698:
694:
690:
686:
662:
560:
533:
529:
504:
502:
497:
494:
489:
484:
483:
472:
469:
464:
463:
432:0.872 g/cm
422:
397:
387:
378:
372:
352:
328:
320:
300:
280:
260:
240:
220:
203:
195:
175:
172:
167:
166:
150:
100:
71:
69:
67:
65:
63:
24:
17:
12:
11:
5:
3851:
3849:
3841:
3840:
3838:Isoamyl esters
3835:
3830:
3825:
3823:Alkyl nitrites
3820:
3815:
3805:
3804:
3798:
3797:
3787:
3784:
3783:
3781:
3780:
3770:
3767:
3760:
3753:
3743:
3733:
3716:
3706:
3702:
3687:ACE inhibitors
3680:
3679:
3674:
3670:
3666:
3661:
3657:
3653:
3648:
3643:
3638:
3629:
3628:
3619:
3607:
3605:
3601:
3600:
3597:
3596:
3594:
3593:
3588:
3582:
3580:
3574:
3573:
3571:
3570:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3526:
3520:
3518:
3512:
3511:
3508:
3507:
3505:
3504:
3499:
3494:
3489:
3484:
3479:
3474:
3469:
3464:
3459:
3454:
3448:
3446:
3442:
3441:
3439:
3438:
3433:
3420:
3407:
3401:
3399:
3393:
3392:
3390:
3389:
3384:
3379:
3366:
3353:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3300:
3295:
3290:
3285:
3280:
3275:
3269:
3267:
3261:
3260:
3258:
3257:
3252:
3247:
3242:
3229:
3216:
3207:
3202:
3197:
3192:
3187:
3182:
3177:
3172:
3167:
3162:
3156:
3154:
3145:
3136:
3122:
3121:
3119:
3118:
3113:
3108:
3103:
3098:
3089:
3088:
3083:
3078:
3073:
3058:
3043:
3042:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
2995:
2994:
2989:
2984:
2969:
2968:
2952:
2947:
2942:
2937:
2932:
2927:
2922:
2917:
2912:
2907:
2902:
2890:-Butyl nitrite
2884:
2882:Pentyl nitrite
2879:
2877:-Butyl nitrite
2871:
2869:Methyl nitrite
2866:
2861:
2856:
2851:
2846:
2841:
2834:alkyl nitrites
2823:
2805:
2804:
2799:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2761:
2756:
2751:
2744:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2702:
2697:
2692:
2687:
2682:
2677:
2672:
2667:
2655:
2653:
2639:
2638:
2635:
2634:
2632:
2631:
2622:
2621:
2616:
2611:
2606:
2601:
2596:
2591:
2586:
2581:
2576:
2567:
2565:
2556:
2550:
2549:
2547:
2546:
2541:
2536:
2530:
2528:
2522:
2521:
2510:
2508:
2507:
2500:
2493:
2485:
2476:
2475:
2472:
2471:
2470:
2469:
2466:
2455:
2449:
2443:
2442:
2439:
2438:
2436:
2435:
2434:
2433:
2423:
2421:Copper sulfate
2417:
2415:
2409:
2408:
2405:
2404:
2402:
2401:
2396:
2395:
2394:
2382:
2377:
2376:
2375:
2362:
2360:
2356:
2355:
2353:
2348:
2343:
2338:
2336:
2335:
2334:
2328:
2323:
2308:
2307:
2305:
2304:
2299:
2294:
2292:Acetylcysteine
2288:
2286:
2278:
2277:
2275:
2274:
2269:
2262:
2260:
2247:
2246:
2244:
2243:
2237:
2235:
2229:
2228:
2226:
2225:
2220:
2219:
2218:
2216:Sodium nitrite
2213:
2201:
2196:
2190:
2188:
2182:
2181:
2179:
2178:
2173:
2167:
2165:
2156:
2152:
2151:
2148:
2147:
2145:
2144:
2133:
2130:Andexanet alfa
2121:
2119:
2117:Anticoagulants
2113:
2112:
2110:
2109:
2103:
2101:
2095:
2094:
2092:
2091:
2085:
2083:
2074:
2066:
2065:
2062:
2061:
2059:
2058:
2052:
2050:
2042:
2041:
2039:
2038:
2033:
2028:
2023:
2018:
2013:
2007:
2005:
1999:
1998:
1996:
1995:
1993:Cholinesterase
1987:
1986:
1985:
1980:
1970:
1965:
1960:
1954:
1952:
1939:
1938:
1936:
1935:
1930:
1924:
1922:
1916:
1915:
1913:
1912:
1907:
1901:
1899:
1895:Benzodiazepine
1891:
1890:
1888:
1887:
1882:
1876:
1874:
1866:
1865:
1863:
1862:
1857:
1851:
1849:
1840:
1832:
1831:
1821:
1819:
1818:
1811:
1804:
1796:
1789:
1788:
1757:
1755:
1752:
1750:
1749:
1728:
1702:
1685:"Amyl Nitrite"
1673:
1654:
1611:
1582:(3): 270–271.
1557:
1550:
1527:
1524:on 2007-09-27.
1500:
1477:
1454:
1427:
1401:
1370:
1356:
1336:
1329:
1303:
1285:
1280:LearnChemistry
1267:
1246:(6): 477–484.
1226:
1205:(7): 541–552.
1185:
1164:
1143:(5): 755–766.
1123:
1105:
1098:
1078:
1060:
1035:
1033:
1030:
1003:The punk band
974:
971:
957:
954:
904:walls and the
886:blood pressure
876:, is a potent
874:alkyl nitrites
861:
858:
812:
811:
807:
801:
797:
793:
789:
766:esterification
762:
761:
757:
741:
738:
715:
711:
707:
703:
696:
692:
688:
684:
661:
658:
657:
656:
625:
602:cleaning agent
598:
571:
565:heart diseases
559:
556:
544:alkyl nitrites
531:
527:
511:
510:
499:
498:
496:
495:
492:
490:
487:
479:
478:
477:
474:
473:
471:
470:
467:
459:
458:
457:
454:
453:
450:
444:
443:
440:
434:
433:
430:
424:
423:
421:
420:
412:
410:
402:
401:
395:
389:
388:
385:
376:
370:
365:
359:
358:
354:
353:
351:
350:
337:
335:
322:
321:
319:
318:
310:
308:
302:
301:
299:
298:
290:
288:
282:
281:
279:
278:
270:
268:
262:
261:
259:
258:
250:
248:
242:
241:
239:
238:
230:
228:
222:
221:
219:
218:
210:
208:
197:
196:
194:
193:
185:
183:
177:
176:
174:
173:
170:
162:
161:
160:
157:
156:
152:
151:
149:
148:
136:
124:
115:
113:
107:
106:
102:
101:
99:
98:
85:
83:
77:
76:
60:
56:
55:
51:
50:
42:
41:
15:
13:
10:
9:
6:
4:
3:
2:
3850:
3839:
3836:
3834:
3831:
3829:
3826:
3824:
3821:
3819:
3816:
3814:
3811:
3810:
3808:
3795:
3794:
3791:
3785:
3778:
3774:
3771:
3768:
3765:
3761:
3758:
3754:
3751:
3747:
3744:
3741:
3737:
3734:
3731:
3727:
3723:
3720:
3717:
3714:
3710:
3703:
3700:
3696:
3692:
3688:
3685:
3682:
3681:
3678:
3675:
3673:
3667:
3665:
3662:
3660:
3654:
3652:
3649:
3647:
3644:
3642:
3639:
3637:
3634:
3631:
3630:
3627:
3620:
3618:
3612:
3609:
3608:
3606:
3602:
3592:
3589:
3587:
3586:Calmidazolium
3584:
3583:
3581:
3579:
3575:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3527:
3525:
3522:
3521:
3519:
3517:
3513:
3503:
3500:
3498:
3495:
3493:
3490:
3488:
3485:
3483:
3480:
3478:
3475:
3473:
3470:
3468:
3465:
3463:
3460:
3458:
3455:
3453:
3450:
3449:
3447:
3443:
3437:
3434:
3432:
3421:
3419:
3408:
3406:
3403:
3402:
3400:
3398:
3394:
3388:
3385:
3383:
3380:
3378:
3367:
3365:
3354:
3352:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3301:
3299:
3296:
3294:
3291:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3270:
3268:
3266:
3262:
3256:
3253:
3251:
3248:
3246:
3243:
3241:
3230:
3228:
3217:
3215:
3208:
3206:
3203:
3201:
3198:
3196:
3193:
3191:
3188:
3186:
3183:
3181:
3178:
3176:
3173:
3171:
3168:
3166:
3163:
3161:
3158:
3157:
3155:
3153:
3149:
3146:
3144:
3140:
3137:
3133:
3127:
3123:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3099:
3097:
3094:
3091:
3090:
3087:
3084:
3082:
3079:
3077:
3074:
3072:
3069:
3067:
3062:
3059:
3057:
3054:
3052:
3048:
3045:
3044:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2997:
2996:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2974:
2971:
2970:
2967:
2964:
2962:
2956:
2953:
2951:
2948:
2946:
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2918:
2916:
2913:
2911:
2908:
2906:
2903:
2901:
2898:
2896:
2891:
2889:
2885:
2883:
2880:
2878:
2876:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2854:Hexyl nitrite
2852:
2850:
2849:Ethyl nitrite
2847:
2845:
2842:
2840:
2837:
2835:
2829:
2817:
2815:
2811:
2807:
2806:
2803:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2760:
2757:
2755:
2752:
2750:
2738:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2681:
2678:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2657:
2656:
2654:
2650:
2644:
2640:
2630:
2627:
2624:
2623:
2620:
2617:
2615:
2612:
2610:
2607:
2605:
2602:
2600:
2597:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2569:
2568:
2566:
2564:
2560:
2557:
2555:
2551:
2545:
2542:
2540:
2537:
2535:
2532:
2531:
2529:
2527:
2523:
2519:
2516:
2513:
2506:
2501:
2499:
2494:
2492:
2487:
2486:
2483:
2467:
2465:
2462:
2461:
2459:
2456:
2453:
2450:
2448:
2445:
2444:
2440:
2432:
2429:
2428:
2427:
2424:
2422:
2419:
2418:
2416:
2414:
2410:
2400:
2397:
2393:
2390:
2389:
2388:
2387:
2383:
2381:
2378:
2374:
2371:
2370:
2369:
2368:
2364:
2363:
2361:
2357:
2352:
2351:Prussian blue
2349:
2347:
2344:
2342:
2339:
2337:
2332:
2329:
2327:
2324:
2322:
2319:
2318:
2317:
2313:
2309:
2303:
2300:
2298:
2295:
2293:
2290:
2289:
2287:
2283:
2279:
2273:
2270:
2268:
2264:
2263:
2261:
2259:
2252:
2248:
2242:
2239:
2238:
2236:
2234:
2230:
2224:
2221:
2217:
2214:
2212:
2209:
2208:
2207:
2206:
2202:
2200:
2197:
2195:
2192:
2191:
2189:
2187:
2183:
2177:
2174:
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2019:
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2011:Diprenorphine
2009:
2008:
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1928:Physostigmine
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1695:September 29,
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1544:. MIT Press.
1543:
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1330:9780123864550
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1099:9783527607495
1095:
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999:
998:
993:
988:
986:
982:
981:
972:
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966:
964:
955:
953:
951:
950:nitroglycerin
947:
943:
939:
935:
931:
927:
923:
919:
915:
911:
907:
903:
899:
895:
891:
887:
883:
882:blood vessels
880:; it expands
879:
875:
866:
859:
857:
855:
854:aryl bromides
851:
847:
846:diiodomethane
844:
840:
836:
832:
828:
823:
821:
817:
810:
787:
786:
785:
783:
778:
776:
771:
770:sulfuric acid
767:
755:
754:
753:
751:
747:
739:
737:
735:
730:
728:
724:
719:
700:
682:
679:
675:
671:
667:
659:
652:
646:
642:
638:
634:
630:
626:
623:
619:
615:
611:
607:
603:
599:
596:
592:
588:
587:Methemoglobin
584:
583:methemoglobin
580:
576:
572:
570:
566:
562:
561:
557:
555:
553:
549:
545:
541:
537:
525:
521:
517:
507:
500:
491:
486:
482:
475:
466:
462:
455:
451:
449:
445:
441:
439:
438:Boiling point
435:
431:
429:
425:
418:
414:
413:
411:
408:
403:
396:
394:
390:
366:
364:
360:
355:
347:
343:
342:DTXSID9025455
339:
338:
336:
327:
323:
316:
312:
311:
309:
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303:
296:
292:
291:
289:
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216:
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137:
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125:
117:
116:
114:
112:
108:
103:
95:
90:
87:
86:
84:
82:
78:
74:
61:
57:
54:Clinical data
52:
48:
43:
39:
34:
26:
22:
3833:Vasodilators
3813:Antianginals
3789:
3788:
3764:paraxanthine
3740:beta blocker
3683:
3632:
3610:
3414:-ornithine (
3347:-ornithine (
3092:
3071:Feprosidnine
3066:Sydnonimines
3064:
3049:
3046:
2998:
2975:
2972:
2961:nitrosamines
2958:
2893:
2887:
2874:
2838:
2831:
2808:
2658:
2625:
2604:GSK-2181236A
2570:
2512:Nitric oxide
2384:
2365:
2312:Toxic metals
2211:Amyl nitrite
2210:
2203:
2081:Beta blocker
1989:
1920:GHB overdose
1769:(12): 1127.
1766:
1762:
1741:. Retrieved
1739:. 2019-05-14
1731:
1719:. Retrieved
1714:
1705:
1693:. Retrieved
1688:
1667:
1657:
1624:
1620:
1614:
1579:
1575:
1539:
1530:
1519:the original
1510:
1503:
1486:
1480:
1463:
1457:
1440:
1436:
1430:
1420:
1414:
1404:
1394:
1386:
1373:
1361:. Retrieved
1346:
1339:
1312:
1306:
1297:
1288:
1279:
1270:
1243:
1239:
1229:
1202:
1198:
1188:
1179:
1173:
1167:
1140:
1136:
1126:
1117:
1088:
1081:
1072:
1063:
1052:. Retrieved
1048:
1039:
1015:
1009:
1002:
995:
992:Derek Jarman
989:
978:
976:
967:
959:
902:blood vessel
894:nitric oxide
871:
843:aryl iodides
824:
813:
779:
763:
750:nitrous acid
743:
734:banapple gas
733:
731:
723:amyl nitrate
720:
701:
674:pentyl group
669:
663:
660:Nomenclature
552:psychoactive
516:Amyl nitrite
515:
514:
503:
111:Legal status
105:Legal status
72:
30:Amyl nitrite
25:
21:Amyl nitrate
3777:simvastatin
3611:Precursors:
3548:epicatechin
3472:Indospicine
3427:-arginine (
3373:-arginine (
3308:AR-C 102222
3236:-arginine (
3223:-arginine (
3086:Sydnonimine
2819:Nitrite (NO
2802:Trolnitrate
2798:Tenitramine
2740:Nitrate (NO
2626:Inhibitors:
2609:Praliciguat
2589:BAY 60-4552
2584:BAY 41-8543
2579:BAY 41-2272
2454:from market
2426:Ipecacuanha
2341:Dimercaprol
2297:Glutathione
2171:Dimercaprol
2070:Circulatory
2045:Reversal of
1983:Pralidoxime
1943:Nerve agent
1905:Cyprodenate
1870:Barbiturate
1182:(1): 37–38.
1137:Circulation
1073:urban75.com
946:synesthesia
930:hypotension
878:vasodilator
614:ozone layer
567:as well as
548:vasodilator
468:CC(C)CCON=O
400: g·mol
155:Identifiers
59:Other names
3807:Categories
3750:sildenafil
3730:nifedipine
3633:Cofactors:
3622:N-Hydroxy-
3529:N-Hydroxy-
3318:Canavanine
3313:BYK-191023
3132:inhibitors
3061:REC15/2739
3040:V-PYRRO/NO
2730:Nicorandil
2619:Vericiguat
2518:modulators
2367:iodine-131
2302:Methionine
2272:Fomepizole
2056:Sugammadex
2036:Naltrexone
2026:Nalorphine
1910:Flumazenil
1855:Metadoxine
1743:2023-12-02
1668:MSD Manual
1363:5 February
1357:158112404X
1175:Toxicology
1054:2023-12-05
1032:References
916:symptoms.
914:withdrawal
816:carbanions
641:depression
405:3D model (
393:Molar mass
315:CHEBI:2691
275:5N0U5TUC9Z
246:ChemSpider
181:CAS Number
164:IUPAC name
3818:Antidotes
3790:See also:
3736:Nebivolol
3695:captopril
3617:-Arginine
3558:norvaline
3553:ornithine
3467:GW-273629
3423:N-Methyl-
3369:N-Methyl-
3360:-lysine (
3232:N-Propyl-
3219:N-Methyl-
3200:ARL-17477
3093:Unsorted:
2643:NO donors
2614:Riociguat
2594:BI-703704
2574:Ataciguat
2515:signaling
2464:Phase III
2452:Withdrawn
2258:poisoning
2141:Protamine
2021:Nalmefene
1990:see also:
1978:Obidoxime
1963:Biperiden
1950:poisoning
1933:SCH-50911
1885:Ethamivan
1880:Bemegride
1823:Antidotes
1536:Cytowic R
1022:Las Vegas
990:The 1978
890:afterload
850:bromoform
522:with the
66:Nitramyl,
3757:caffeine
3722:blockers
3713:bosentan
3699:losartan
3516:Arginase
3502:VAS-2381
3497:ONO-1714
3445:Unsorted
3205:Indazole
3111:FR146881
3106:FR144220
3096:Cimlanod
3051:Furoxans
3030:PROLI/NO
3000:NONOates
2950:SNO-t-PA
2814:nitrites
2725:NCX-4215
2720:NCX 4040
2715:NCX-4016
2710:NCX-2216
2660:Nitrates
2649:prodrugs
2346:Edetates
2331:thallium
2251:Methanol
2176:Succimer
2135:against
2124:against
2089:Glucagon
2031:Naloxone
2016:Doxapram
1968:Diazepam
1958:Atropine
1897:overdose
1872:overdose
1860:Thiamine
1641:17382831
1606:11971852
1538:(2003).
1489:: 1249.
1381:(1943).
1379:Noyes WA
1262:20653465
1221:19650716
956:Toxicity
942:fainting
926:vomiting
918:Overdose
906:internal
818:to give
775:decanted
746:alcohols
629:inhalant
622:perfumes
506:(verify)
226:DrugBank
190:110-46-3
81:ATC code
3775:(e.g.,
3773:Statins
3748:(e.g.,
3724:(e.g.,
3711:(e.g.,
3693:(e.g.,
3543:ginseng
3492:NXN-462
3487:NCX-456
3477:KD-7040
3457:CKD-712
3190:A-84643
3056:Furoxan
2955:SNO-vWF
2705:NCX-466
2554:Targets
2326:mercury
2316:cadmium
2267:Ethanol
2205:nitrite
2137:heparin
1836:Nervous
1771:Bibcode
1721:8 April
1689:Toxbase
1649:5903121
1597:1725875
1466:: 859.
1298:PubChem
1159:4954412
997:Jubilee
980:Columbo
839:halogen
835:radical
804:OH +
666:isomers
651:Poppers
645:anxiety
633:cocaine
616:, as a
606:solvent
591:cyanide
579:oxidant
569:angina.
540:nitrite
524:formula
428:Density
398:117.148
363:Formula
235:DB01612
201:PubChem
97:)
91: (
89:V03AB22
73:poppers
3604:Others
3563:lysine
3126:Enzyme
3101:FK-409
3015:GLO/NO
2966:SIN-1A
2447:WHO-EM
2413:Emetic
2072:system
1973:Oximes
1838:system
1647:
1639:
1621:Lancet
1604:
1594:
1548:
1354:
1327:
1260:
1219:
1157:
1096:
1026:angina
940:, and
922:nausea
820:oximes
649:(see:
461:SMILES
295:D00517
132:
3636:NADPH
3431:-NMA)
3418:-NIO)
3377:-NMA)
3364:-NIL)
3351:-NIO)
3293:AEITU
3288:1400W
3240:-NPA)
3227:-NMA)
3214:-NIO)
2900:LA810
2526:Forms
2359:Other
2155:Other
1827:V03AB
1645:S2CID
1522:(PDF)
1515:(PDF)
1014:book
994:film
831:amine
748:with
681:alkyl
518:is a
481:InChI
407:JSmol
306:ChEBI
3651:Heme
3578:CAMK
3397:eNOS
3387:TRIM
3338:MITU
3333:IPTU
3328:EITU
3265:iNOS
3255:TRIM
3152:nNOS
3020:JS-K
2888:tert
2321:lead
1723:2023
1697:2020
1637:PMID
1602:PMID
1546:ISBN
1423:: 87
1365:2017
1352:ISBN
1325:ISBN
1258:PMID
1217:PMID
1155:PMID
1094:ISBN
1010:The
977:The
908:and
806:NaNO
710:CHCH
670:amyl
637:MDMA
604:and
558:Uses
536:amyl
286:KEGG
266:UNII
255:7762
215:8053
3664:CaM
3646:FMN
3641:FAD
3591:W-7
3524:ABH
3303:AMT
3143:NOS
2629:ODQ
2563:sGC
1779:doi
1629:doi
1625:369
1592:PMC
1584:doi
1491:doi
1468:doi
1445:doi
1317:doi
1248:doi
1207:doi
1180:168
1145:doi
687:(CH
643:or
635:or
331:EPA
205:CID
94:WHO
3809::
3728::
3705:ET
3697:,
3677:Ca
3656:BH
3063:;
2963:):
2957:;
2892:;
2836:):
2830:;
2460::
1777:.
1767:73
1765:.
1713:.
1687:.
1676:^
1666:.
1643:.
1635:.
1623:.
1600:.
1590:.
1580:19
1578:.
1574:.
1560:^
1441:55
1439:.
1421:82
1419:.
1413:.
1392:;
1385:.
1323:.
1296:.
1278:.
1256:.
1244:48
1242:.
1238:.
1215:.
1203:39
1201:.
1197:.
1178:.
1153:.
1141:32
1139:.
1135:.
1108:^
1071:.
1047:.
1028:.
936:,
932:,
928:,
924:,
856:.
822:.
802:11
794:11
784::
752::
736:.
714:CH
695:CH
585:.
532:11
377:11
140:US
128:UK
120:DE
3779:)
3766:)
3759:)
3752:)
3742:)
3738:(
3732:)
3715:)
3707:B
3701:)
3689:/
3671:2
3669:O
3658:4
3624:L
3615:L
3531:L
3429:L
3425:L
3416:L
3412:L
3375:L
3371:L
3362:L
3358:L
3349:L
3345:L
3238:L
3234:L
3225:L
3221:L
3212:L
3134:)
3130:(
3068::
3053::
2979::
2875:n
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2824:2
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2812:/
2749:)
2745:3
2662::
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2647:(
2504:e
2497:t
2490:v
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2139:(
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1829:)
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1631::
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1474:.
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1333:.
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1264:.
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1102:.
1075:.
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808:2
800:H
798:5
792:H
790:5
788:C
758:2
716:2
712:2
708:2
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704:3
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689:2
685:3
655:.
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624:.
530:H
528:5
526:C
409:)
386:2
383:O
380:N
374:H
371:5
368:C
333:)
329:(
142::
130::
23:.
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