Pentyl Nitrite Research Articles

Jungle juice causing pseudohypercholesterolaemia

Background: A twenty-one-year old female presented to the emergency department with cyanosed lips after consuming 3– 5mL of Jungle Juice (pentyl nitrite) with seven standard drinks of ethanol over the course of six hours. Her skin appeared grey suggesting progressive hypoxaemia, blood paracetamol level was undetectable and urine drug screen (Roche Cobas c501) was negative for cannabinoids, barbiturates, amphetamines and opiates. Methylene blue was commenced immediately and a follow-up venous blood gas fourr hours after admission (Radiometer ABL 800) showed pH: 7.35, pO2: 20.4 mmHg, pCO2: 46.0 mmHg, Na: 143 mmol/L, K: 4.2 mmol/L, Cl: 119 mmol/L, bicarbonate: 24.8 mmol/L, creatinine: 92 umol/L, ionised Ca: 1.18 mmol/L and glucose: 5.4 mmol/L. Paired peripheral venous sample performed on the Roche Cobas c501 for electrolytes gave similar results, but the chloride was significantly different: 104 mmol/L. The calculated anion gap (AG) resulting from the ABL 800 is falsely low 3 (7–17), compared to 22 (7–17) from the Roche Cobas c501. Conclusion: This illustrates that nitrate from the metabolism of pentyl nitrite may be preferentially selected by chloride electrodes impregnated with certain ionophores, causing falsely high chloride levels. In an unconscious patient, this presents a challenge to clinicians to determine the cause.

Isopropyl Nitrite Induced Hemoglobin Oxidation in Diabetics Blood

The effect of isopropyl nitrite on human Type 2 Diabetes blood was undertaken using non diabetics blood as the control group. The differences in patient characteristics such as the mean ages and weights of the two groups were not statistically significant (P>0.05), and the ratios of non-smokers to smokers were similar meaning that the two groups were well matched. These studies revealed that diabetics erythrocytes with a mean HbA1C value ± SEM of 11.4 ± 0.27% were oxidized at a significantly greater rate than that of the control blood (P<0.05). The isopropyl nitrite mean oxidation time ± SEM of diabetics blood was 1.5 ± 0.05 min (n = 20). For the nondiabetics blood a mean HbA1C ± SEM value of 5.5 ± 0.08% was obtained with a mean oxidation time ± SEM of the non-diabetics blood of 4.6 ± 0.13 min (n=20). These studies demonstrate that Diabetes blood has an enhanced susceptibility of oxidation into methemoglobin by isopropyl nitrite compared to its respective control group, i.e., the normal blood. This finding could be attributed to the fact that isopropyl nitrite is a nitrite ester which contains a saturated three hydrocarbon chain similar to other analogous nitrite esters (ethyl nitrite, butyl nitrite, pentyl nitrite and hexyl nitrite) which also contain saturated hydrocarbon chains that previously showed a statistically significant increased oxidation time for diabetics blood (P<0.05) [1-6]. Thus this study confirms that the difference in the number of methylene molecules has no impact on the rate of oxidation on either diabetics blood or nondiabetics blood (P>0.05). These findings also imply that the increased susceptibility to isopropyl nitrite induced oxidation reaction in diabetics blood is a direct function of the amount of HbA1C present in the blood, i.e., a clear inverse relation appears to exist between the amount of HbA1C present and the oxidation time

ChemInform Abstract: Metal‐Free Nitrative Cyclization of N‐Aryl Imines with tert‐Butyl Nitrite: Dehydrogenative Access to 3‐Nitroindoles.

AbstractThe cyclization works well with tert‐butyl nitrite only while similar reagents iso‐butyl or n‐amyl nitrite give preferentially β‐nitroethylidene derivatives, e.

ChemInform Abstract: Azo Pigments and Their Intermediates. A Reinvestigation of the Tetrazotization of 1,4-Diaminoanthraquinone.

The azotization of 1,4-diaminoanthraquinone (1) by n-amyl nitrite in glacial acetic was reinvestigated. The structure of a red-brown precipitate, which was previously identified as anthraquinone-1,4-tetrazonium dichloride (3) by Schaarschmidt, was found to be incorrect. In this work, we have identified the red-brown solid as 4-aminoanthraquinone-1-diazonium chloride (2), a diazotized product of 1. The yield of 2 was 80%. The tetrazonium dichloride 3 was actually formed in minute quantity and is soluble in acetic acid. The tetrazonium product of 1 can be isolated as tetrafluoroborate salt 4 in 3.4% yield by adding fluoboric acid into the acetic acid solution. The structure 4 was confirmed by IR and cross-polarization magic angle spinning13C NMR spectroscopy. Further investigations showed that 1 can be quantitatively tetrazotized by nitrosylsulfuric acid in 78% sulfuric acid. The tetrazonium product was isolated as 4 in 74% yield. Key words: 1,4-diaminoanthraquinone, diazotization, tetrazotization, azo pigm...

Facile Synthesis of 8, 2′-S-Cyclopurine Nucleoside

This paper describes the synthesis of 8,2 -anhydro-8-mercapto-9-(β-D-arabinofuranosyl)purine (8,2′-S-cyclopurinenucleoside, 1) via the shorter route from 3′,5′-di-O-acectyl-8,2′-S-cycloadenosine (6) and by direct reductive deamination with n- pentyl nitrite in tetrahydrofuran (THF) and deacetylation. The preparation of 8,2′-S-cycloadenosine (2) was achieved in good yield by the cyclization of the protected 8-mercaptoadenosine with triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF at room temperature, under Mitsunobu reaction conditions.

Hydrocyanation of some α,β-unsaturated ketones, and the synthesis of some unusual isoxazoles

β-Cyano-α-methylcycloalkanones are regiospecifically nitrosated at the α-position by pentyl nitrite in methanolic sodium methoxide to give fused isoxazolo-lactams via a pathway probably involving sequential cycloalkanone cleavage, isoxazole formation and lactamisation. The chemistry of some new compounds derived from the hydrocyanation products of (–)-carvone is described.

Addition Reaction of Benzyne to C60

Abstract Benzyne generated by the reaction of 2-aminobenzoic acid and pentyl nitrite in a refluxing benzene was found to add to C60 in good yield. The reaction products were separated by HPLC to give C60(C6H4), C60(C6H4)2, C60(C6H4)3, and C60(C6H4)4, which were confirmed by mass spectra. 1H NMR spectrum of C60(C6H4) is consistent with the structure of mono-addition product, whereas those of C60(C6H4)2, C60(C6H4)3, and C60(C6H4)4 indicate that they consist of the corresponding mixtures of isomers.

Azo pigments and their intermediates. A reinvestigation of the tetrazotization of 1,4-diaminoanthraquinone

The azotization of 1,4-diaminoanthraquinone (1) by n-amyl nitrite in glacial acetic was reinvestigated. The structure of a red-brown precipitate, which was previously identified as anthraquinone-1,4-tetrazonium dichloride (3) by Schaarschmidt, was found to be incorrect. In this work, we have identified the red-brown solid as 4-aminoanthraquinone-1-diazonium chloride (2), a diazotized product of 1. The yield of 2 was 80%. The tetrazonium dichloride 3 was actually formed in minute quantity and is soluble in acetic acid. The tetrazonium product of 1 can be isolated as tetrafluoroborate salt 4 in 3.4% yield by adding fluoboric acid into the acetic acid solution. The structure 4 was confirmed by IR and cross-polarization magic angle spinning13C NMR spectroscopy. Further investigations showed that 1 can be quantitatively tetrazotized by nitrosylsulfuric acid in 78% sulfuric acid. The tetrazonium product was isolated as 4 in 74% yield. Key words: 1,4-diaminoanthraquinone, diazotization, tetrazotization, azo pigments.

Mutagenicity of some alkyl nitrites used as recreational drugs

When the AIDS epidemic was in its earliest stages, and prior to identification of HIV as the etiological factor, the use of volatile nitrites by the male homosexual community to enhance sexual activities appeared to have a significant role in this disease. Preliminary observations indicated that the portion of the male homosexual community which developed Kaposi's sarcoma were also heavy nitrite users. These nitrites had been demonstrated to be mutagenic in bacteria and thus it was postulated that they could be responsible for the appearance of the sarcoma. To evaluate further the genotoxic activity of these chemicals, six nitrites, including those most commonly used by homosexuals for sexual gratification, were selected for testing in the mouse lymphoma TK+/- and Salmonella typhimurium mutagenicity assays. One chemical, n-amyl nitrite, was negative in the mouse lymphoma assay, while the other five chemicals, n-butyl, isobutyl, iso-amyl, sec-butyl, and n-propyl nitrite, were positive. All six compounds were positive in the Salmonella assay. The mutagenic and known toxic effects of these chemicals remain a concern because a large population of teenagers and young adults continue to abuse these substances.

ChemInform Abstract: Potential ZNS‐Effective, Tricyclic Compounds with a Bridged Middle Ring. Part 1. Reaction of Benzo(c)furans with Benzyne.

AbstractDiels‐Alder reaction of dehydrobenzene (II), in situ prepared from anthranilic acid (I) by treatment with pentyl nitrite, with the furans (III) gives the epoxynaphthalenes (IV) which are hydrogenated to yield the epoxytetralins (V).

ChemInform Abstract: TRANSFORMATION PRODUCTS OF BENZAZOYLHYDRAZONES OF ALDEHYDES IN ACETIC ACID IN THE PRESENCE OF N‐AMYL NITRITE

Chemischer InformationsdienstVolume 15, Issue 7 Heterocyclic Compounds ChemInform Abstract: TRANSFORMATION PRODUCTS OF BENZAZOYLHYDRAZONES OF ALDEHYDES IN ACETIC ACID IN THE PRESENCE OF N-AMYL NITRITE G. N. LIPUNOVA, G. N. LIPUNOVASearch for more papers by this authorN. A. KLYUEV, N. A. KLYUEVSearch for more papers by this authorL. I. MEDVEDEVA, L. I. MEDVEDEVASearch for more papers by this authorN. P. BEDNYAGINA, N. P. BEDNYAGINASearch for more papers by this authorV. G. ZHIL'NIKOV, V. G. ZHIL'NIKOVSearch for more papers by this author G. N. LIPUNOVA, G. N. LIPUNOVASearch for more papers by this authorN. A. KLYUEV, N. A. KLYUEVSearch for more papers by this authorL. I. MEDVEDEVA, L. I. MEDVEDEVASearch for more papers by this authorN. P. BEDNYAGINA, N. P. BEDNYAGINASearch for more papers by this authorV. G. ZHIL'NIKOV, V. G. ZHIL'NIKOVSearch for more papers by this author First published: February 14, 1984 https://doi.org/10.1002/chin.198407250Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume15, Issue7February 14, 1984 RelatedInformation

Products of transformation of aldehyde benzazolylhydrazones in acetic acid in the presence of n-amyl nitrite

The reaction of aldehyde benzazolylhydrazones with amy1 nitrite in acetic acid leads to an oxidative transformation to give N,N′-diacyl derivatives of 2-hydrazinobenzazoles rather than to nitrosation of the hydrazones, whereas in the case of benzaldehyde benzothiazolylhydrazone it leads to 1,4-dibenzothiazolyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine.

A novel synthetic method for γ-acetoxy-( E)-α,β-unsaturated esters by the palladium catalyzed regio- and stereoselective acetoxylation of β,γ-unsaturated esters

A new synthetic method for γ-acetoxy-α,β-unsaturated esters by the acetoxylation of β,γ-unsaturated esters catalyzed by PdCl 2 in the presence of KOAc and pentyl nitrite in acetic acid is presented. The reaction takes place at γ-position of the esters regioselectively with double bond migration to α,β-position. The E configuration of the double bond was confirmed by NMR analysis. Preliminary investigation to synthesize pyrenophorin and pyrenophorol using this reaction is described.

Synthesis and structures of alkyl (aryl) benzazolylazoketoximes

Alkyl(aryl)benzazolylazoketoximes were obtained by nitrosation of the hydrazones of alkyl- and aryl-substituted aldehydes by means of n-amyl nitrite. On the basis of data from IR and PMR spectroscopy it was concluded that the synthesized compounds exist in the oxime form. Their acid ionization constants were determined.

ChemInform Abstract: THE RELATIVE REACTIVITIES OF THE SEVEN NUCLEAR POSITIONS OF ISOQUINOLINE TO FREE‐RADICAL PHENYLATION

Free-radical phenylation of isoquinoline has been effected both by photolysis of phenylthallium(III) di(trifluoroacetate) and by the action of pentyl nitrite on aniline. Analysis of the isomeric phenyl isoquinoline mixture by g.l.c. and h.p.l.c. established the reactivity order in the isoquinoline nucleus to be 1 > 5 > 8 > 4 > 3,6,7. This experimental order is compared with the eight published theoretical predictions, none of which is correct.

Oxidative demethylation of α- and γ-methyl-N-heterocyclonium salts: a new method for preparation of N-substituted-α- and -gamma;-oxo-N-heterocycles

1-Substituted-2-methyl- and -4-methyl-pyridinium cations are converted by pentyl nitrite and sodium methoxide into 1-substituted-2- and -4-pyridones respectively.

The Relative Reactivities of the Seven Nuclear Positions of Isoquinoline to Free-Radical Phenylation

Free-radical phenylation of isoquinoline has been effected both by photolysis of phenylthallium(III) di(trifluoroacetate) and by the action of pentyl nitrite on aniline. Analysis of the isomeric phenyl isoquinoline mixture by g.l.c. and h.p.l.c. established the reactivity order in the isoquinoline nucleus to be 1 > 5 > 8 > 4 > 3,6,7. This experimental order is compared with the eight published theoretical predictions, none of which is correct.

Identification by e.s.r. spectroscopy of pentyloxyphenylnitroxyl and diphenylnitroxyl radicals during the reaction of aniline and pentyl nitrite

AbstractThe e.s.r. signal observed during the reaction of aniline and pentyl nitrite in benzene is shown to be due not to phenyldiazoxyl (PhNNO·), as previously reported, but to a mixture of pentyloxyphenylnitroxyl and diphenylnitroxyl radicals, this assignment being made with the aid of deuterium labelling and on the basis of their observed hyperfine coupling constants and g values.

In situ formation of arenediazonium salts and aryl radicals by aprotic nitrosation of 1,3-diaryltriazenes: dual halogen abstraction from bromotrichloromethane, and radical arylation of aromatic compounds

Nitrosation of 1,3-diaryltriazenes (XC6H4·NHN2·C6H6X; X = H, 4-Me, 4-MeO, 4-Cl, 4-NO2, 2-Me, 2-Cl, or 3-Cl) by pentyl nitrite in benzene at 80 °C, and subsequent in situ decomposition of the resulting N-nitroso-1,3-diaryltriazenes, gives biaryls (XC6H4Ph)(54–142 mol per 100 mol of triazene). 1-(4-Chlorophenyl)-3-phenyltriazene gives a mixture of 4-chlorobiphenyl (66 mol per 100 mol) and biphenyl (65 mol per 100 mol). That aryl radicals are involved follows (a) from the formation of 2-(18.5%), 3-(49.5%), and 4-(32%) t-butylbiphenyls (total yield 106 mol per 100 mol) on nitrosation of 1,3-diphenyltriazene in t-butylbenzene, and (b) from the relative extents of reaction of this nitrosated triazene with benzene and chlorobenzene (excess of an equimolar mixture; ratio 1 : 1.6, respectively). Reaction of pentyl nitrite with 1,3-diphenyltriazene in bromotrichloromethane at 15 °C gives a precipitate of benzenediazonium chloride (80 mol per 100 mol). Also formed are bromobenzene (33), chlorobenzene (21), carbon dioxide (10), and pentyl carbanilate (10) mol per 100 mol). At 50 °C the reaction gave chlorobenzene (61) and bromobenzene (49); addition of 1,1-diphenylethene led to an almost complete reversal of these proportions. These results provide another example of anomalous dual halogen abstraction from bromotrichloromethane and support the general mechanism for this type of reaction outlined in the preceding paper.

Acylarylnitrosamines. Part X. An electron spin resonance spectroscopic investigation of the reactions of aryl radicals with tetraphenylcyclopentadienone and 2,3-diarylindenones : detection of 1-oxo-2,2,3-triphenylindenyl and related radicals and their relevance to dienonepromoted formation of benzyne from benzenediazonium acetate

Decomposition of benzenediazonium acetate, formed in situ in benzene from N-nitrosoacetanilide (NNA), in the presence of tetraphenylcyclopentadienone (tetracyclone) gives e.s.r. signals corresponding to new long lived radicals (4) formed by addition of a phenyl radical to position 2 of tetracyclone. Similar reactions of NNA with 2,3-diphenylindenone gave long lived signals corresponding to the 1-oxo-2,2,3-triphenylindenyl radical (5), an assignment supported by computer simulation. The use of dibenzoyl peroxide or pentyl nitrite–aniline as alternative sources of phenyl radicals also led to the formation of radical (5). The assignments of structures (4) and (5) were supported by analysis of the related signals obtained from reactions of NNA with 2-phenyl-3-(p-t-butylphenyl)- and 3-phenyl-2-(p-t-butylphenyl)-indenone, and by reactions of p-t-butyl-NNA with 2,3-diphenylindenone and with 2-phenyl-3-(p-t-butylphenyl)indenone. Related studies with 2-methyl-3,4,5-triphenyl-, 2,5-diethyl-3,4-diphenyl-, and 3,4-diphenyl-2,5-di-p-tolylcyclo-pentadienones were also carried out. These results with those described in the preceding paper lend support to the suggestion that benzyne promotion from NNA by tetracyclone and 2,3-diphenylindenone is explicable on the basis of inhibition of the competing NNA-derived radical chain phenylation of the solvent.