Evaluation of Six Aromatic Amines in the Mainstream Smoke of Commercial Cigars

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This article references 33 other publications.

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   Masuda, Y.; Hoffmann, D. Quantitative Determination of 1-Naphthylamine and 2-Naphthylamine in Cigarette Smoke. Anal. Chem. 1969, 41 (4), 650– 652,  DOI: 10.1021/ac60273a017

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   Determination of 1-naphthylamine and 2-naphthylamine in cigaret smoke

   Masuda, Yoshito; Hoffmann, Dietrich

   Analytical Chemistry (1969), 41 (4), 650-2CODEN: ANCHAM; ISSN:0003-2700.

   A method is described for the anal. of 1-naphthylamine (I) and 2-naphthylamine (II) in cigarette smoke. The basic nonvolatiles of the smoke of 300 cigarettes are reacted with pentafluoropropionic anhydride and the resulting neutral components are chromatographed on Florisil. The concns. of N-pentafluoropropionamides of I and II are analyzed by gas chromatog. with an electron capture detector, which has a sensitivity limit of <1 ng. 14C-labeled I and II served as internal standards. The mainstream smoke of an 85-mm. U.S. nonfilter cigarette contained 27 ng. of I and 22 ng. of II. Although the identification of 2-naphthylamine in cigarette smoke represents the first isolation of a known bladder carcinogen from a nonoccupational respiratory environment, no biol. significance can as yet be attached to this finding.

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   Pieraccini, G.; Luceri, F.; Moneti, G. New gas-chromatographic/mass spectrometric method for the quantitative analysis of primary aromatic amines in main- and side- stream cigarette smoke. I. Rapid Commun. Mass Spectrom. 1992, 6 (6), 406– 409,  DOI: 10.1002/rcm.1290060611

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   New gas-chromatographic/mass-spectrometric method for the quantitative analysis of primary aromatic amines in main- and side-stream cigarette smoke. I

   Pieraccini, G.; Luceri, F.; Moneti, G.

   Rapid Communications in Mass Spectrometry (1992), 6 (6), 406-9CODEN: RCMSEF; ISSN:0951-4198.

   A sensitive and accurate method to quantitate 17 primary arom. amines in tobacco smoke was set up. Two Italian com. brands of cigarette were smoked in a home-made smoking machine; the amines in the smoke were trapped in dil. hydrochloric acid (contg. 2H5-aniline, 13C1-o-toluidine and 2H9-4-aminobiphenyl as internal stds.) and, after extn. and purifn., derivatized as pentafluoropropionamides and measured by gas chromatog./mass spectrometry in the selected-ion-monitoring mode. These results confirmed that side-stream smoke contains total levels of arom. amines about 50-60 times higher than those of main-stream smoke and that the smoke of black-tobacco cigarettes is richer in arom. amines compared to light-tobacco cigarettes.

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8. 8

   Luceri, F.; Pieraccini, G.; Moneti, G.; Dolara, P. Primary Aromatic Amines from Side-Stream Cigarette Smoke are Common Contaminants of Indoor Air. Toxicol Ind. Health 1993, 9 (3), 405– 413,  DOI: 10.1177/074823379300900302

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   Primary aromatic amines from side-stream cigarette smoke are common contaminants of indoor air

   Luceri, Francesca; Pieraccini, Giuseppe; Moneti, Gloriano; Dolara, Piero

   Toxicology and Industrial Health (1993), 9 (3), 405-13CODEN: TIHEEC; ISSN:0748-2337.

   A very sensitive mass-spectrometry method was developed for the anal. of arom. amines in tobacco smoke and indoor air. Cigarets were smoked with a smoking machine; the amines from the smoke were trapped in a 5% HCl water soln. contg. internal stds. and detected by gas chromatog./mass spectrometry in the selected-ion-monitoring (SIM) mode. The amines were: aniline, 2-toluidine, 3-toluidine, 4-toluidine, 2-ethylaniline, 3-ethylaniline, 4-ethylaniline, 2,3-dimethylaniline, 2,4-dimethylaniline, 2,5-dimethylaniline, 2,6-dimethylaniline, 1-naphthylamine, 2-naphthylamine, 2-methyl-1-naphthylamine, 2-aminobiphenyl, 3-aminobiphenyl and 4-aminobiphenyl. Nine brands of cigarettes in Italy (Gauloise, Nazionali, Marlboro, Camel, MS, MS mild and MS lights), with and without filter, were analyzed. Main-stream smoke contained a lower amt. of arom. amines than side-stream smoke: the total level of these amines in main-stream smoke was 200-1300 ng/cigarette, whereas the level of arom. amines in side-stream smoke was 20,000-30,000 ng/cigarette. The smoke of black-tobacco cigarettes had higher levels of arom. amines compared to light-tobacco cigarettes and the filters significantly reduced arom. amines in main-stream smoke. The levels of arom. amines were detd. in ambient air, offices, and houses. Some arom. amines (aniline and toluidine) were detected in ambient.

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   Stabbert, R.; Schäfer, K. H.; Biefel, C.; Rustemeier, K. Analysis of aromatic amines in cigarette smoke. Rapid Commun. Mass Spectrom. 2003, 17 (18), 2125– 2132,  DOI: 10.1002/rcm.1161

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   Analysis of aromatic amines in cigarette smoke

   Stabbert, Regina; Schaefer, Karl-Heinz; Biefel, Christine; Rustemeier, Klaus

   Rapid Communications in Mass Spectrometry (2003), 17 (18), 2125-2132CODEN: RCMSEF; ISSN:0951-4198. (John Wiley & Sons Ltd.)

   A method for the anal. of o-toluidine, o-anisidine, 2-naphthylamine, and 4-aminobiphenyl in cigarette mainstream smoke has been developed, which combines the sensitivity of their pentafluoropropionyl (PFP) derivs. in neg. ion chem. ionization (NICI) mode with the selectivity of the gas chromatog./tandem mass spectrometry (GC/MS/MS) technique. The use of four deuterated analogs as internal stds. along with the application of the std. addn. method results in accurate and precise results; the interday precision for the arom. amines was 3-10% and the accuracy ranged from 97-100%. This method was applied to two American-blend University of Kentucky ref. cigarettes, eight American-blend market cigarettes, a bright (flue-cured) tobacco cigarette, and an elec. heated cigarette smoking system (EHCSS). For the American-blend cigarettes there was a linear correlation between arom. amine yields and mainstream smoke "tar" ("tar" = total particulate matter - (nicotine + water)), whereas the bright tobacco cigarette and the EHCSS demonstrated significantly lower arom. amine yields on an equal "tar" basis. The results support the hypothesis that the nitrogen content of the tobacco, and above all the cigarette combustion temp., are detg. factors for the yields of arom. amines in smoke.

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    Counts, M. E.; Morton, M. J.; Laffoon, S. W.; Cox, R. H.; Lipowicz, P. J. Smoke composition and predicting relationships for international commercial cigarettes smoked with three machine-smoking conditions. Regul. Toxicol. Pharmacol. 2005, 41 (3), 185– 227,  DOI: 10.1016/j.yrtph.2004.12.002

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    Smoke composition and predicting relationships for international commercial cigarettes smoked with three machine-smoking conditions

    Counts, M. E.; Morton, M. J.; Laffoon, S. W.; Cox, R. H.; Lipowicz, P. J.

    Regulatory Toxicology and Pharmacology (2005), 41 (3), 185-227CODEN: RTOPDW; ISSN:0273-2300. (Elsevier)

    The study objectives were to det. the effects of smoking machine puffing parameters on mainstream smoke compn. and to express those effects as predicting relationships. Forty-eight com. Philip Morris USA and Philip Morris International cigarettes from international markets and the 1R4F ref. cigarette were machine-smoked using smoking conditions defined by the International Organization of Standardization (ISO), the Massachusetts Department of Public Health (MDPH), and Health Canada (HC). Cigarette tobacco fillers were analyzed for nitrate, nicotine, tobacco-specific nitrosamines (TSNA), and ammonia. Mainstream yields for tar and 44 individual smoke constituents and "smoke pH" were detd. Cigarette constituent yields typically increased in the order ISO < MDPH < HC. Relative yield increases were generally greater for cigarettes with higher initial filter ventilation and were also generally greater for vapor-phase constituents than for particulate-phase constituents. Predicting relationships were developed between ISO tar and ISO, MDPH, and HC constituent yields and between MDPH tar and HC tar and resp. smoking condition yields. MDPH and HC constituent yields could be predicted with similar reliability using ISO tar or the corresponding smoking-condition tar. The reliability of the relationships varied from strong to weak, depending on particular constituents. Weak predicting relationships for nitrogen oxides and TSNA's, for example, were improved with inclusion of tobacco filler compn. factors. "Smoke pH" was similar for all cigarettes at any one smoking condition, and overall marginally lower at HC conditions than at ISO or MDPH conditions.

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11. 11

    Ai, J.; Hassink, M.; Taylor, K. M.; Deycard, V. N.; Hearn, B.; Williams, K. Hydrogen Cyanide and Aromatic Amine Yields in the Mainstream Smoke of 60 Little Cigars. Chem. Res. Toxicol. 2022, 35 (6), 940– 953,  DOI: 10.1021/acs.chemrestox.1c00330

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    Hydrogen Cyanide and Aromatic Amine Yields in the Mainstream Smoke of 60 Little Cigars

    Ai, Jiu; Hassink, Matthew; Taylor, Kenneth M.; Deycard, Victoria Nicole; Hearn, Bryan; Williams, Katrice; McGuigan, Megan; Valentin-Blasini, Liza; Watson, Clifford H.

    Chemical Research in Toxicology (2022), 35 (6), 940-953CODEN: CRTOEC; ISSN:0893-228X. (American Chemical Society)

    Mainstream smoke yields of hydrogen cyanide (HCN), and three arom. amines, 1-aminonaphthalene, 2-aminonaphthalene and 4-aminobiphenyl from 60 little cigar brands currently on the US market were measured for both International Organization for Standardization (ISO) and Canadian Intense (CI) smoking regimens. The smoke yields are compared with those from 50 cigarette products measured by Counts et al. of Philip Morris USA (PMUSA) in 2005 and 50 cigarette products measured by Centers for Disease Control and Prevention (CDC) in cooperation with the Food and Drug Administration (FDA) in 2012. For the little cigars, the av. HCN yield with the ISO smoking regimen is 335μg/cigar (range: 77-809μg/cigar), which is 332% higher than the av. of 50 PMUSA 2005 cigarettes and 243% higher than the av. of 50 CDC/FDA 2012 cigarettes, resp. For the CI smoking regimen, the av. HCN yield is 619μg/cigar (range: 464-1045μg/cigar), which is 70.5% higher than the av. of 50 PMUSA 2005 cigarettes and 69% higher than the 50 CDC/FDA 2012 cigarettes, resp. For arom. amines, the av. ISO smoking regimen smoke yields are 36.6 ng/cigar (range: 15.9-70.6 ng/cigar) for 1-aminonaphthalene, 24.6 ng/cigar (range: 12.3-36.7 ng/cigar) for 2-aminonaphthalene and 5.6 ng/cigar (range: 2.3-17.2 ng/cigar) for 4-aminobiphenyl, resp. The av. ISO yields of arom. amines from little cigars are 141% to 210% higher compared to the av. yields of 50 PMUSA cigarettes. The av. CI smoke regimen yields are 73.0 ng/cigar (range: 32.1-112.2 ng/cigar) for 1-aminonaphthalene, 45.2 ng/cigar (range: 24.6-74.8 ng/cigar) for 2-aminonaphthalene and 12.7 ng/cigar (range: 5.5-37.5 ng/cigar) for 4-aminobiphenyl, resp. The av. CI arom. amine yields are 143% to 220% higher compared to the av. yields of 50 PMUSA cigarettes, almost identical to the relative yields under the ISO smoking regimen. Both HCN and arom. amine yields are 1.5x to 3x higher for the tested little cigars than conventional cigarettes, however there are notable differences in the relationships of these yields to certain product characteristics, such as wt., ventilation and tobacco type. The higher smoke yields of these compds. from little cigars indicates that cigar smokers may be at risk of higher exposure to HCN and arom. amines on a per stick basis and thus contributing to an increased health risk.

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    Wang, X.; Kim, Y.; Borowiecki, M.; Tynan, M. A.; Emery, S.; King, B. A. Trends in Cigar Sales and Prices, by Product and Flavor Type - the United States 2016–2020. Nicotine Tob. Res. 2022, 24 (9), 1519  DOI: 10.1093/ntr/ntac038

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    Erratum to: Trends in Cigar Sales and Prices, by Product and Flavor Type-the United States, 2016-2020

    Wang Xu; Tynan Michael A; King Brian A; Kim Yoonsang; Borowiecki Mateusz; Emery Sherry

    Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco (2022), 24 (9), 1519 ISSN:.

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    Park-Lee, E.; Ren, C.; Cooper, M.; Cornelius, M.; Jamal, A.; Cullen, K. A. Tobacco Product Use Among Middle and High School Students─United States, 2022. MMWR Morb. Mortal. Wkly. Rep. 2022, 71, 1429– 1435,  DOI: 10.15585/mmwr.mm7145a1

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    Tobacco Product Use Among Middle and High School Students - United States, 2022

    Park-Lee Eunice; Ren Chunfeng; Cooper Maria; Cornelius Monica; Jamal Ahmed; Cullen Karen A

    MMWR. Morbidity and mortality weekly report (2022), 71 (45), 1429-1435 ISSN:.

    Tobacco use* is the leading cause of preventable disease, disability, and death among adults in the United States (1). Youth use of tobacco products in any form is unsafe, and nearly all tobacco use begins during youth and young adulthood (2). The Food and Drug Administration (FDA) and CDC analyzed data from the 2022 National Youth Tobacco Survey (NYTS) to estimate current (past 30-day) use of eight tobacco products among U.S. middle (grades 6-8) and high school (grades 9-12) students. In 2022, approximately 11.3% of all students (representing 3.08 million persons) reported currently using any tobacco product, including 16.5% of high school and 4.5% of middle school students (2.51 million and 530,000 persons, respectively). Electronic cigarettes (e-cigarettes) were the most commonly used tobacco product among high school (14.1%; 2.14 million) and middle school (3.3%; 380,000) students. Approximately 3.7% of all students (representing 1 million persons) reported currently smoking any combustible tobacco product. Current use of any tobacco product was higher among certain population groups, including 13.5% of non-Hispanic American Indian or Alaska Native (AI/AN)(†) students; 16.0% of students identifying as lesbian, gay, or bisexual (LGB); 16.6% of students identifying as transgender; 18.3% of students reporting severe psychological distress; 12.5% of students with low family affluence; and 27.2% of students with low academic achievement. Implementation of comprehensive evidence-based tobacco control strategies, combined with FDA regulation, is important for preventing and reducing youth tobacco product use (1,2).

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    National Academies of Sciences, Engineering, and Medicine. Premium Cigars: Patterns of Use, Marketing, and Health Effects; The National Academies Press: Washington, DC, 2022.

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    TTB (Alcohol and Tobacco Tax and Trade Bureau). Federal excise tax increase and related provisions 2017 https://www.ttb.gov/main-pages/federal-excise-tax-inrease-and-related-provisions (accessed January 15, 2023).

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    Gammon, D. G.; Loomis, B. R.; Dench, D. L.; King, B. A.; Fulmer, E. B.; Rogers, T. Effect of price changes in little cigars and cigarettes on little cigar sales: USA, Q4 2011–Q4 2013. Tobacco Control 2016, 25 (5), 538– 544,  DOI: 10.1136/tobaccocontrol-2015-052343

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    Effect of price changes in little cigars and cigarettes on little cigar sales: USA, Q4 2011-Q4 2013

    Gammon Doris G; Loomis Brett R; Dench Daniel L; Rogers Todd; King Brian A; Fulmer Erika B

    Tobacco control (2016), 25 (5), 538-44 ISSN:.

    INTRODUCTION: Little cigars are comparable to cigarettes in terms of shape, size, filters and packaging. Disproportionate tobacco excise taxes, which directly affect purchase price, may lead consumers to substitute cigarettes with less expensive little cigars. This study estimated the effects of little cigar and cigarette prices on little cigar sales. METHODS: Sales data from a customised retail scanner database were used to model a log-log equation to infer own-price and cross-price elasticity of demand for little cigars relative to little cigar and cigarette prices, respectively, from quarter 4 of 2011 to quarter 4 of 2013. Data were available for convenience stores (C-stores) (n=29 states); food, drug and mass merchandisers (FDMs) (n=44 states); and C-stores and FDMs combined (n=27 states). The dependent variable was per capita little cigar pack sales, and key independent variables were the price index for little cigars and cigarettes. RESULTS: A 10% increase in little cigar price was associated with a 25% (p<0.01) decrease in little cigar sales in C-stores alone, and a 31.7% (p<0.01) decrease in C-stores and FDMs combined. A 10% increase in cigarette price was associated with a 21.5% (p<0.05) increase in little cigar sales in C-stores, and a 27.3% (p<0.01) increase in C-stores and FDMs combined. CONCLUSIONS: Our results suggest that US cigarette smokers are avoiding the high cost of cigarettes by switching to lower priced little cigars. Increasing and equalising prices among comparable products, like cigarettes and little cigars, may motivate cost-conscious smokers to quit.

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    Piadé, J. J.; Wajrock, S.; Jaccard, G.; Janeke, G. Formation of mainstream cigarette smoke constituents prioritized by the World Health Organization - Yield patterns observed in market surveys, clustering and inverse correlations. Food Chem. Toxicol. 2013, 55, 329– 347,  DOI: 10.1016/j.fct.2013.01.016

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    Formation of mainstream cigarette smoke constituents prioritized by the World Health Organization - Yield patterns observed in market surveys, clustering and inverse correlations

    Piade, J.-J.; Wajrock, S.; Jaccard, G.; Janeke, G.

    Food and Chemical Toxicology (2013), 55 (), 329-347CODEN: FCTOD7; ISSN:0278-6915. (Elsevier Ltd.)

    The WHO TobReg proposed mandating ceilings on selected smoke constituents detd. from the market-specific median of nicotine-normalized yield distributions. Data validating this regulatory concept were obtained from essentially single-blend surveys. This process is strongly impacted by inverse correlations among yields. In the present study, 18 priority WHO smoke constituent yields (nicotine-normalized) were detd. (using two smoking regimens) from 262 com. brands including American, Virginia and local blends from 13 countries. Principal Component Anal. was used to identify yields patterns, clustering of blend types and the inverse correlations causing these clusters. Three principal components explain about 75% of total data variability. PC1 was sensitive to the relative levels of gas- and particle-phase compds. PC2 and PC3 cluster American- and Virginia-blends, revealing inverse correlations: Nitrogen oxides and amino- or nitroso-arom. compds. inversely correlate to either formaldehyde and acrolein, or benzo(a)pyrene and di-hydroxybenzenes. These results can be explained by reviewing the processes detg. each components smoke delivery. Regulatory initiatives simultaneously targeting selected smoke constituents in markets with mixed blend styles will be strongly impacted by the inverse correlations described. It is difficult to predict the ultimate impact of such regulations on public health, considering the complex chem. of cigarette smoke formation.

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    Torikai, K.; Uwano, Y.; Nakamori, T.; Tarora, W.; Takahashi, H. Erratum to Study on tobacco components involved in the pyrolytic generation of selected smoke constituents. Food Chem. Toxicol. 2005, 43 (9), 1449  DOI: 10.1016/j.fct.2005.02.010

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    Study on tobacco components involved in the pyrolytic generation of selected smoke constituents. [Erratum to document cited in CA142:368888]

    Torikai, K.; Uwano, Y.; Nakamori, T.; Tarora, W.; Takahashi, H.

    Food and Chemical Toxicology (2005), 43 (9), 1449CODEN: FCTOD7; ISSN:0278-6915. (Elsevier B.V.)

    The name of the first author, K. Torikai, was misspelled.

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    Patrianakos, C.; Hoffmann, D. Chemical Studies on Tobacco Smoke LXIV. On the Analysis of Aromatic Amines in Cigarette Smoke. J. Anal. Toxicol. 1979, 3 (4), 150– 154,  DOI: 10.1093/jat/3.4.150

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    Chemical studies on tobacco smoke. LXIV. On the analysis of aromatic amines in cigarette smoke

    Patrianakos, Constantin; Hoffmann, Dietrich

    Journal of Analytical Toxicology (1979), 3 (4), 150-4CODEN: JATOD3; ISSN:0146-4760.

    The amines from cigarette smoke were trapped in dil. HCl and enriched together with the basic portion, derivatized to pentafluoropropionamides and detd. by gas chromatog. with a 63Ni-electron capture detector (detection limit 50 pg aniline/ cigarette). The mainstream smoke of 1 US 85-mm cigarette without filter tip contained 102 ng of aniline [62-53-3], 61 ng of 2- [95-53-4], 3- [108-44-1], and 4-toluidine (I) [106-49-0], 55.8 ng of ethyl- [103-69-5] and dimethylaniline, 4,3 ng of 1-naphthylamine [134-32-7], 6.9 ng 2- [90-41-5], 3- [2243-47-2] and 4-aminobiphenyl [92-67-1] and 5.8 ng of 2-methyl-1-naphthylamine [2246-44-8]. Sidestream smoke contained levels of arom. amines 20-68 times higher than those in the mainstream smoke. The results from smoke analyses of exptl. cigarettes supported the concept that the nitrate content and the protein content of tobacco were detg. factors for the smoke yields of arom. amines. The possible biologic implications of this study were discussed.

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    Yoshida, S.; Kobayashi, K. Roles of tobacco fractions in the formation of polycyclic aromatic amines in tobacco pyrolysis. Beitr. Tabakforsch. Int./Contrib. Tob. Res. 2013, 25 (6), 595– 606,  DOI: 10.2478/cttr-2013-0936

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    Teng, Z.; Wang, Q. Extraction, identification and characterization of the water-insoluble proteins from tobacco biomass. J. Sci. Food Agric. 2012, 92 (7), 1368– 1374,  DOI: 10.1002/jsfa.4708

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    Extraction, identification and characterization of the water-insoluble proteins from tobacco biomass

    Teng, Zi; Wang, Qin

    Journal of the Science of Food and Agriculture (2012), 92 (7), 1368-1374CODEN: JSFAAE; ISSN:0022-5142. (John Wiley & Sons Ltd.)

    BACKGROUND: Tobacco leaves are a potential candidate for plant proteins, yielding fourfold more protein per acre than soybeans. However, more than 60% of these proteins are water-insol. and remain in the residue (referred to as tobacco biomass) after aq. extn. Efficient extn. of tobacco biomass proteins (TBPs) could boost the development of value-added products from tobaccos. RESULTS: TBPs were resistant to salt extn. at pH 2.0-12.0, but they were readily extd. by org. solvents. A simplified extg. method, including mech. homogenization, a first extn. with a methanol-water mixt. (40/60, vol./vol.) and a second one with water at pH 6.0, recovered at most 68% of the TBPs. Anal. by sodium dodecyl sulfate-polyacrylamide gel electrophoresis indicated the presence of both the water-sol. tobacco F1 protein and the less sol. cell wall proteins in TBPs, while Fourier transform IR spectra suggested the coexistence of TBPs with polysaccharides (esp. pectin). Meanwhile, a higher content of hydrophobic amino acids was found in TBPs compared with water-extractable tobacco proteins. The amino acid score of TBPs was 0.71, with cysteine and methionine being the primary limiting amino acids. CONCLUSION: Satisfying recovery of TBPs was achieved using a two-step org. solvent extn. The hydrophobicity and protein-pectin interaction of TBPs explained for this result.

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    Fantozzi, P.; Sensidoni, A. Protein extraction from tobacco leaves: technological, nutritional and agronomical aspects. Qual. Plant. - Plant Foods Hum. Nutr. 1983, 32, 351– 368,  DOI: 10.1007/BF01091194

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    Protein extraction from tobacco leaves: technological, nutritional and agronomical aspects

    Fantozzi, Paolo; Sensidoni, Alessandro

    Qualitas Plantarum - Plant Foods for Human Nutrition (1983), 32 (3-4), 351-68CODEN: QLPLAN; ISSN:0377-3205.

    Tobacco studies with the objectives of (1) obtaining smoking material with lowered toxicity and (2) utilizing tobacco leaves as an alternative source of food protein are reported. The results indicate the feasibility of reducing the toxicity of the tobacco smoke by extg. protein from the green leaves prior to curing. The cured deproteinized tobacco can be utilized in smoking products without alteration of taste. The compn. of tobacco protein conc. showed superior qualities of in vivo and in vitro digestibilities, being highest among a series of vegetable proteins studied. Agronomically, use of high planting densities and high levels of N fertilizers resulted in high yields of total protein from tobacco (1794 kg/ha).

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23. 23

    FDA science forum. 2021 https://www.fda.gov/science-research/fda-science-forum/data-visualization-us-tobacco-companies-their-products-and-market-shares (accessed January 20, 2023).

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24. 24

    CORESTA. Recommended Method No. 46: Atmosphere for Conditioning and Testing Cigars of all Sizes and Shapes 2018 https://www.coresta.org/sites/default/files/technical_documents/main/CRM_46-June2018.pdf (accessed January 20, 2020).

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    CORESTA. Recommended Method No. 64: Routine Analytical Cigar-Smoking Machine - Specifications, Definitions and Standard Conditions 2018 https://www.coresta.org/sites/default/files/technical_documents/main/CRM_64-May2018.pdf (accessed January 20, 2020).

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26. 26

    Ji, H.; Jin, Z. Analysis of six aromatic amines in the mainstream smoke of tobacco products. Anal. Bioanal. Chem. 2022, 414, 4227– 4234,  DOI: 10.1007/s00216-022-04075-7

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    Analysis of six aromatic amines in the mainstream smoke of tobacco products

    Ji, Huihua; Jin, Zhenyu

    Analytical and Bioanalytical Chemistry (2022), 414 (14), 4227-4234CODEN: ABCNBP; ISSN:1618-2642. (Springer)

    Arom. amines are a class of carcinogenic compds. in tobacco smoke that are listed on the FDA list of harmful and potentially harmful constituents (HPHCs). A method using solid-phase microextn.-coupled to gas chromatog.-triple quadrupole mass spectrometry (SPME headspace GC-MS/MS) was developed and validated for the quant. detn. of six arom. amines, including 1-aminonaphthalene (1-AN), 2-aminonaphthalene (2-AN), 3-aminobiphenyl (3-ABP), 4-aminobiphenyl (4-ABP), o-toluidine (o-TOL), and o-anisidine (o-ANI), in the mainstream smoke of cigarettes, cigars, and heated tobacco products. The method developed here combines high sensitivity with simple sample prepn. and has demonstrated satisfactory linearity for all six arom. amines with correlation coeffs. greater than 0.9994. The limits of detection range and the limits of quantitation range were 12-96 pg/mL and 41-320 pg/mL, resp. Their recoveries and coeffs. of variation (CV%) were 90-112% and 2.1-6.6%, resp. The new SPME headspace GC/MS/MS method has been successfully applied to measure the contents of the six arom. amines in the mainstream smoke of cigarettes, cigars, and heated tobacco products.

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27. 27

    G-Bioscience https://cdn.gbiosciences.com/pdfs/protocol/786-247_protocol.pdf (accessed April 8, 2022).

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28. 28

    Turesky, R. J.; Le Marchand, L. Metabolism and biomarkers of heterocyclic aromatic amines in molecular epidemiology studies: Lessons learned from aromatic amines. Chem. Res. Toxicol. 2011, 24 (8), 1169– 1214,  DOI: 10.1021/tx200135s

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    Metabolism and Biomarkers of Heterocyclic Aromatic Amines in Molecular Epidemiology Studies: Lessons Learned from Aromatic Amines

    Turesky, Robert J.; Le Marchand, Loic

    Chemical Research in Toxicology (2011), 24 (8), 1169-1214CODEN: CRTOEC; ISSN:0893-228X. (American Chemical Society)

    A review. Arom. amines and heterocyclic arom. amines (HAAs) are structurally related classes of carcinogens that are formed during the combustion of tobacco or during the high-temp. cooking of meats. Both classes of procarcinogens undergo metabolic activation by N-hydroxylation of the exocyclic amine group to produce a common proposed intermediate, the arylnitrenium ion, which is the crit. metabolite implicated in toxicity and DNA damage. However, the biochem. and chem. properties of these compds. are distinct, and different biomarkers of arom. amines and HAAs have been developed for human biomonitoring studies. Hb adducts have been extensively used as biomarkers to monitor occupational and environmental exposures to a no. of arom. amines; however, HAAs do not form Hb adducts at appreciable levels, and other biomarkers have been sought. A no. of epidemiol. studies that have investigated dietary consumption of well-done meat in relation to various tumor sites reported a pos. assocn. between cancer risk and well-done meat consumption, although some studies have shown no assocns. between well-done meat and cancer risk. A major limiting factor in most epidemiol. studies is the uncertainty in quant. ests. of chronic exposure to HAAs, and thus, the assocn. of HAAs formed in cooked meat and cancer risk has been difficult to establish. There is a crit. need to establish long-term biomarkers of HAAs that can be implemented in mol. epidemiol. studies. In this review, we highlight and contrast the biochem. of several prototypical carcinogenic arom. amines and HAAs to which humans are chronically exposed. The biochem. properties and the impact of polymorphisms of the major xenobiotic-metabolizing enzymes on the biol. effects of these chems. are examd. Lastly, the anal. approaches that have been successfully employed to biomonitor arom. amines and HAAs, and emerging biomarkers of HAAs that may be implemented in mol. epidemiol. studies are discussed.

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29. 29

    Hu, W.; Cai, W.; Zheng, Z. Study on the chemical compositions and microbial communities of cigar tobacco leaves fermented with exogenous additive. Sci. Rep. 2022, 12, 19182  DOI: 10.1038/s41598-022-23419-y

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    29

    Study on the chemical compositions and microbial communities of cigar tobacco leaves fermented with exogenous additive

    Hu, Wanrong; Cai, Wen; Zheng, Zhaojun; Liu, Yuanfa; Luo, Cheng; Xue, Fang; Li, Dongliang

    Scientific Reports (2022), 12 (1), 19182CODEN: SRCEC3; ISSN:2045-2322. (Nature Portfolio)

    Fermn. process plays an important role in the biochem. properties and quality of cigar tobacco leaves (CTLs). In industry, exogenous additive (EA) was usually adopted for improving the quality of CTLs during fermn. However, the mechanism of enhanced quality of CTLs fermented with EA was confused. Herein, the chem. compns. and microbial communities of CTLs during fermn. with EA were analyzed. The increased contents of total nitrogen and total sugar, as well as the improved consumption rate of reducing sugar in CTLs were found with the addn. of EA. Besides, fermn. with EA reduced the content of total nonvolatile org. acid, esp. unsatd. fatty acid. The contents of total and several representative aroma components were improved. Addnl., the increased abundance of Staphylococcus and decreased abundance of Aspergillus were detected. Combined with the changes of chem. compns. and microbial communities, it was confirmed that the carbohydrates and alcs. originated from EA promote the enrichment of Staphylococcus and accelerate biochem. reactions, such as Maillard reaction and esterification reaction, thus improving the contents and quality of aroma components in CTLs. This study demonstrated the mechanism of enhanced quality of CTLs fermented by EA, which provides more ideas for developing novel and efficient EAs.

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30. 30

    Li, J.; Zhao, Y.; Qin, Y.; Shi, H. Influence of microbiota and metabolites on the quality of tobacco during fermentation. BMC Microbiol. 2020, 20 (1), 356  DOI: 10.1186/s12866-020-02035-8

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    30

    Influence of microbiota and metabolites on the quality of tobacco during fermentation

    Li, Jingjing; Zhao, Yuanyuan; Qin, Yanqing; Shi, Hongzhi

    BMC Microbiology (2020), 20 (1), 356CODEN: BMMIBC; ISSN:1471-2180. (BioMed Central Ltd.)

    To explore the optimum fermn. conditions for tobacco leaves and also screen the microbiota and metabolites that are beneficial for fermn. Tobacco leaves were fermented at 25 °C, 35 °C, and 45 °C for 2, 4, and 6 wk, resp. For identification of the best fermn. temp., physicochem. properties and sensory quality of fermented tobacco were investigated. Subsequently, based on the appropriate temp., 16 s rRNA sequencing and metabolomics anal. of tobacco were performed to monitor the change of microbes and metabolites during fermn. process (from 2 to 6 wk). Sensory quality anal. indicated that fermn. at 45 °C for 6 wk represented the optimum condition. Metabolomics anal. showed that a total of 415 metabolites were annotated. The increase of fermn. period led to significant changes of metabolites. Results revealed an increase in concn. of L-phenylalanine and sphingosine as well as decreased concn. of betaine and phytosphingosine with the prolongation of fermn. period (2 to 6 wk). Distinct changes in the microbiota were also obsd. with prolongation of the fermn. time. Results revealed that Pseudomonas, Pantoea, and Burkholderia were dominant bacteria in fermn. at 45 °C for 6 wk. With the extension of the fermn. time, the abundance of Pseudomonas increased, while that of Sphingomonas and Methylobacterium decreased. Furthermore, microbiota profiles were tightly relevant to the altered metabolites, esp. compds. involved in the sphingolipid metab. Suitable fermn. conditions were 45 °C for 6 wk; phytosphingosine and sphingosine might affect tobacco fermn. via the sphingolipid metab. pathway. This study provides a theor. basis for guiding tobacco fermn. and gives insights into reducing harmful substances during tobacco fermn.

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31. 31

    Chen, J.; Li, Y.; He, X.; Jiao, F.; Xu, M.; Hu, B. Influences of different curing methods on chemical compositions in different types of tobaccos. Ind. Crops Prod. 2021, 167, 113534  DOI: 10.1016/j.indcrop.2021.113534

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    31

    Influences of different curing methods on chemical compositions in different types of tobaccos

    Chen, Jie; Li, Yan; He, Xian; Jiao, Fangchan; Xu, Meiling; Hu, Binbin; Jin, Yan; Zou, Congming

    Industrial Crops and Products (2021), 167 (), 113534CODEN: ICRDEW; ISSN:0926-6690. (Elsevier B.V.)

    Whether quality can be improved and style characteristics of different types of tobaccos can be changed after being cured using different methods has not been clear yet. It is necessary to explore the influences of different curing methods on chem. compns. of different types of tobaccos. For this purpose, by taking flue-cured tobacco K326, burley tobacco Yunbai 3 and oriental tobacco Basma 14 as materials, the effects of air-curing, sun-curing and flue-curing methods on chem. compns. of these three types of tobaccos were investigated by taking the freeze-dried tobacco as the control group based on the equil. method of matter loss. The results show that compared with freeze-dried tobacco, (1) The air-cured, flue-cured and sun-cured were displayed in a descending order in terms of the dry matter loss and dry matter loss rate of K326, burley and oriental tobaccos thereby. (2) After performing air-cured, sun-cured and flue-cured, the starch contents in the oriental and flue-cured tobaccos greatly reduce while their contents of the total sugar and reducing sugar rose; the contents of starch and reducing sugar in the burley tobacco both decreased. (3) The contents of protein, total nitrogen and nicotine in the three types of air-cured, sun-cured and flue-cured tobaccos all significantly decreased. (4) The redn. amts. of the pigment content in the sun-dried burley and flue-cured tobaccos were the largest while that in the flue-cured oriental tobacco reaches the largest. (5) The total polyphenol contents in the three types of tobaccos all significantly reduced after being air-cured, sun-cured and flue-cured. The total polyphenol contents in the flue-cured and burley tobaccos were significantly larger than those in air-cured and sun-cured ones; the total polyphenol content in the sun-cured oriental tobacco was significantly larger than those in the groups treated with other curing methods. (6) The potassium (K) and chlorine (Cl) contents in the three types of tobaccos processed by the other curing methods were relatively stable. (7) The sensory evaluation scores of flue-cured tobaccos, burley tobacco and oriental tobacco were higher after flue-cured based on Yunnan sensory evaluation method. The study clarifies the transformation law of chem. compns. in different types of tobaccos under different curing methods. A type of tobaccos is not only limited to single curing method. It is feasible to combine multiple curing methods to enrich the style characteristics of tobaccos.

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32. 32

    Myers, M. Talk about a Scoop: Tobacco company puts kitty litter in its cigars. https://www.tobaccofreekids.org/press-releases/2013_03_01_kittylitter (accessed February 20, 2023).

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33. 33

    Reilly, S. M.; Goel, R.; Bitzer, Z.; Elias, R. J.; Foulds, J.; Muscat, J.; Richie, J. P., Jr. Little Cigars, Filtered Cigars, and their Carbonyl Delivery Relative to Cigarettes. Nicotine Tob. Res. 2018, 20, S99– S106,  DOI: 10.1093/ntr/ntx274

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    33

    Little cigars, filtered cigars, and their carbonyl delivery relative to cigarettes

    Reilly, Samantha M.; Goel, Reema; Bitzer, Zachary; Elias, Ryan J.; Foulds, Jonathan; Muscat, Joshua; Richie, John P., Jr.

    Nicotine & Tobacco Research (2018), 20 (suppl_1), S99-S106CODEN: NTREF6; ISSN:1469-994X. (Oxford University Press)

    Introduction: Little cigars and filtered cigars are currently growing in popularity due to their low cost and wide variety of flavors while retaining an appearance similar to cigarettes. Given the health consequences assocd. with cigarette use, it is important to understand the potential harm assocd. with these similar products. This includes the potential harm assocd. with carbonyls (eg, acetaldehyde, acrolein, formaldehyde, etc.), an important class of toxicants and carcinogens in tobacco smoke. Our objective was to det. the carbonyl levels in mainstream smoke from little and filtered cigars compared to cigarettes. Methods: We examd. two brands each of little cigars and filtered cigars, as well as two research cigarettes for carbonyl delivery using the International Organization of Stds. (ISO) and the Health Canada Intense (HCI) machine-smoking protocols. Results: On a per puff basis, the levels of five of the seven carbonyls were higher from little cigars than filtered cigars and cigarettes (ISO: 56-116%; HCI: 39-85%; p < .05). On a per unit basis, most carbonyl levels were higher from both cigar types than cigarettes using the ISO method (ISO: 51-313%; p < .05) whereas only filtered cigars were higher using the HCI method (HCI: 53-99%; p < .05). Conclusion: These findings suggest that cigar smokers can be exposed to higher levels of carbonyls per cigar than cigarette smokers per cigarette. Implications: These data will increase our understanding of the relative harm from carbonyl exposure from little and filtered cigars both for cigar-only smokers and the cumulative harm among the growing population of cigarette-cigar multi-product smokers.

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