Cyclohexyl Nitrite Research Articles

Nitrite inhalants spontaneously liberate nitric oxide, which is not responsible for the immunotoxicity in C57BL/6 mice

Nitrite inhalant abuse has been correlated epidemiologically with HIV seropositivity and with Kaposi’s sarcoma. Using a mouse model, we have shown that inhaled isobutyl nitrite caused anemia and severely depressed immunity. In the present study, we showed that both isobutyl and cyclohexyl nitrites in air liberated nitric oxide (NO). An immunotoxic dose of 900 ppm isobutyl nitrite liberated 115 ppm NO. Mice were exposed in an inhalation chamber to 115 ppm NO, 900 ppm isobutyl nitrite, or 900 ppm cyclohexyl nitrite for 45 min/day. Following a single exposure, NO did not affect peripheral blood cell counts, while isobutyl and cyclohexyl nitrites reduced cell numbers. After 14 daily exposures, isobutyl nitrite, but not cyclohexyl nitrite or NO, reduced peritoneal macrophage tumoricidal activity. The nitrite esters likely caused immunotoxicity by mechanisms other than NO release.

Cyclohexyl Nitrite Encounter

A brown glass bottle containing yellow liquid was submitted for examination for the presence of common controlled substances. While no controlled substances were detected, the liquid was identified as impure cyclohexyl nitrite, a compound of the same chemical class as amyl and butyl nitrite, which are known for their abuse potential. A bottle labeled cyclohexyl nitrite, but not confirmed by analysis, is the only known previous case submitted to this lab. The case history, examination, and analytical results are presented.

Acute blood toxicity of the abused inhalant, cyclohexyl nitrite

Cyclohexyl nitrite is an abused nitrite inhalant. This is the first report of toxicity of cyclohexyl nitrite. Mice were exposed to 300–900 ppm cyclohexyl nitrite in an inhalation chamber for 45 min and then bled. Such treatment resulted in a 7–10% reduction in red blood cell counts, haemoglobin and haematocrit levels. Both blood leucocyte counts and spleen cellularity were reduced by 40%. Unlike isobutyl nitrite, subchronic treatment of mice with cyclohexyl nitrite did not impair macrophage tumoricidal activity or production of reactive nitrogen intermediates, but did modulate B and T cell mitogen responses. The data suggest that cyclohexyl nitrite had cytotoxic activity, comparable to that of isobutyl nitrite, which might be related to the anaemia reported in abusers. The immunomodulatory properties of cyclohexyl nitrite differed from those of isobutyl nitrite.

Determination of cyclamate in soft drinks by reaction with nitrous acid. II. Manual and semi-automated methods: determination of cyclohexyl nitrite by diazotisation and coupling with Bratton--Marshall reagent.

The determination of cyclamate at a concentration of approximately 1 mg ml–1 in soft drinks is described. Cyclohexyl nitrite, derived from cyclamate by reaction of the latter with nitrous acid, is determined in a non-aqueous system by initial diazotisation with sulphanilamide and subsequent coupling with 2-aminoethyl-1-naphthylamine. Manual and semi-automated procedures have been evaluated and interference has been studied.

A comparative kinetic study of the N‐Nitrosation of sulfanilamide by cyclohexyl nitrite and by nitrous acid

AbstractA comparative study of the kinetics of the N‐nitrosation of sulfanilamide by cyclohexyl nitrite and by nitrous acid has been made, using an automated technique. The results indicate that a common nitrosating species is effective in analogous reactions involving cyclohexyl nitrite or nitrous acid. The N‐nitrosation reaction has been followed spectrophotometrically by coupling the diazotized product with 1‐naphthol. Under certain conditions a competitive reaction takes place in which coupling occurs with unreacted sulfanilamide.

Determination of cyclamate in soft drinks by reaction with nitrous acid. Gas-liquid chromatographic determination of cyclohexene and of cyclohexyl nitrite.

Gas-liquid chromatographic determinations of cyclohexene and of cyclohexyl nitrite, formed by reaction of cyclamate with nitrous acid under moderate or strong nitrosating conditions, have been evaluated. The determination based on the formation of cyclohexene under moderate nitrosating conditions proved to be the most precise and sensitive. The application of this procedure to the determination of cyclamate in soft drinks (ten orange and ten lemon drinks) gave recoveries of 98 to 101 per cent. at the 1 mg ml–1 level; reaction conditions were evaluated and compared with those used by previous workers.

Colorimetric Determination of Cyclamate

A colorimetric method for the determination of cyclamate in foods, based on the reaction of cyclohexanol with vanillin-sulfuric acid reagent, was established. After separation of cyclamate from other components by dialysis pretreatment, cyclamate was converted to cyclohexyl nitrite with nitrous acid under cooling in an ice bath and then to cyclohexanol with sulfamic acid. Cyclohexanol was extracted with ether. After the addition of water to the extract, the ether was evaporated by vigorous stirring using a mixer at room temperature. Vanillin-sulfuric acid reagent was added little by little to the remaining water layer containing cyclohexanol under cooling in an ice bath and warmed for 20 minutes at 70°to form a greenish product. The colored solution was measured spectrophotometrically at 655 mμ. The recovery of sodium cyclamate added to some foods was 93.2-98.8%.

Formation of Lower Nitro Alkanes by Vapor Phase Nitration of Cyclic Hydrocarbons

Vapor-phase nitration of cyclohexane and cyclohexyl nitrite produces primary nitro alkanes, the yield of which decreases with decreasing number of carbon atoms. Both their structure and relative ratios of formation lead to the conclusion that they are formed from 1-pentyl radical, which in turn is formed from cyclohexoxyl radical. The intermediate phases are radical reactions already known from the vapor-phase oxidation of hydrocarbons.

N-Nitrosation of N-cyclohexylsulphamic acid

The action of nitrous acid on cyclamic acid (N-cyclohexylsulphamic acid) has been investigated and the organic products formed in the reaction have been identified. Using strong nitrosating conditions, cyclohexyl nitrite is formed (76 %) together with cyclohexene (23 %). The effect of reaction conditions on the yield of these products has been studied using GLC. The evidence suggests that in strong nitrosating conditions cyclohexanol, formed by N-nitrosation, is quantitatively converted to cyclohexyl nitrite.

Studies on Analysis of Food Additives (XX)

Sodium cyclamate, which had been forbidden to use as food additive to any kinds of foods, was separated from other food components by ultrafiltration and determined by colorimeteric method.It has been reported that sodium cyclamate reacts with nitrite and turns into cyclohexyl nitrite.In this report, the experimental condition for the colorimetric determination of the cyclohexyl nitrite was examined. Sulfanilamide and N-1-naphthylethylenediamine dihydrochloride were used as the reagents. The colored solution was determined at about 555mμ. of wave length Ultrafiltration method was found to be very effective for preparing the test solution, and the prepared test solution could be used for esterification directly without dilution, the solution not being emulsified with organic solvent on extraction procedure.In the recovery test of cyclamate on food, the recovery ratio was about 90%.The minimum limit concentrations of detectable sodium cyclamate were 50ppm in juice and was 500ppm in the other foods.

Gas Chromatography of Sodium Cyclamate (II)

Gas chromatographic procedure for the determination of sodium cyclamate was studied. According to recent studies, it has been reported that sodium cyclamate reacts with nitrite and produces cyclohexanol, cyclohexanone and cyclohexene. The author's experiment showed that the major product of the reaction was cyclohexyl nitrite, together with some cyclohexanol and slight cyclohexene in the presence of excess nitrite at temp. below 5°C.Using the blended liquid phase column consisting of DC-550 and DEGS (10% of each) on Gaschrom P (60/80mesh) at 60°C, carrier gas nitrogen (60ml/min) and a flame ionization detector, cyclohexyl nitrite and cyclohexanol were investigated. The results are given in Fig. 1- (C) and 2.Sodium cyclamate was determined on the basis of the cyclohexyl nitrite. The cyclohexyl nitrite was prepared by treating varying amounts of sodium cyclamate with 5ml of 10% sodium nitrite and 4ml of 10% sulfuric acid in ice water and it was extracted with 10ml of n-hexane containing 0.25 v/v% n-decane as internal standard and then injected to the Shimazu gas chromatograph.The relation between peak heights of cyclohexyl nitrite and amounts of sodium cyclamate was linear in the range of 20-600mg of the latter, and in this case, cyclohexanol did not appeared. But, when excessive amounts (>800mg) of sodium cyclamate were present, the yield of cyclohexyl nitrite diminished and that of cyclohexanol increased. The minimum limit of detection was approximately 0.1μg as sodium cyclamate.

Gas Chromatography of Sodium Cyclamate

Gas chromatographic procedure for the determination of sodium cyclamate was studied. According to recent studies, it has been reported that sodium cyclamate reacts with nitrite and produces cyclohexanol, cyclohexanone and cyclohexene. The author's experiment showed that the major product of the reaction was cyclohexyl nitrite, together with some cyclohexanol and slight cyclohexene in the presence of excess nitrite at temp. below 5°C.Using the blended liquid phase column consisting of DC-550 and DEGS (10% of each) on Gaschrom P (60/80mesh) at 60°C, carrier gas nitrogen (60ml/min) and a flame ionization detector, cyclohexyl nitrite and cyclohexanol were investigated. The results are given in Fig. 1- (C) and 2.Sodium cyclamate was determined on the basis of the cyclohexyl nitrite. The cyclohexyl nitrite was prepared by treating varying amounts of sodium cyclamate with 5ml of 10% sodium nitrite and 4ml of 10% sulfuric acid in ice water and it was extracted with 10ml of n-hexane containing 0.25 v/v% n-decane as internal standard and then injected to the Shimazu gas chromatograph.The relation between peak heights of cyclohexyl nitrite and amounts of sodium cyclamate was linear in the range of 20-600mg of the latter, and in this case, cyclohexanol did not appeared. But, when excessive amounts (>800mg) of sodium cyclamate were present, the yield of cyclohexyl nitrite diminished and that of cyclohexanol increased. The minimum limit of detection was approximately 0.1μg as sodium cyclamate.

Hygienic Chemical Studies on Food Additives (VIII)

In generally, sodium cyclamate has been determined by EDTA method. However, this method is complicated and time-consuming.In this report, studies on the infrared spectrometric analysis of cyclohexyl nitrite which was derived from sodium cyclamate by sodium nitrite, are described.The results obtained are as follows:1. The absorption of cyclohexyl nitrite in IR-region by carbon tetrachloride was applied to the analysis of sodium cyclamate.2. For the quantitative analysis, 1, 645cm-1 is useful as key band for cyclohexyl nitrite.3. The influence of the other food additives and saccharides were investigated, and the determination of sodium cyclamate was found possible.4. This method was applied to several samples contained synthetic sweetening agents and the recovery of sodium cyclamate was 97.0-100.7%.

929. Conformational studies by nuclear magnetic resonance. Part VI. Adjacently deuterated 2-, 3-, and 4-methylcyclohexanol esters, cyclohexyl nitrite, and cyclo-octyl acetate

929. Conformational studies by nuclear magnetic resonance. Part VI. Adjacently deuterated 2-, 3-, and 4-methylcyclohexanol esters, cyclohexyl nitrite, and cyclo-octyl acetate