Masonic Cancer Center

Comprehensive Cancer Center designated by the National Cancer Institute

GOAL

Cigarette relighting – implications for tobacco constituents

A.Alcheva1,2, A.Farah3, M.Steinberg4, C.Heckman4, O.Wackowski4, C.Delnevo4, D.Hatsukami2,5,6, I.Stepanov1,2

University of Minnesota - Division of Environmental Health Sciences1; Masonic Cancer Center2; College of Biological Sciences3; Rutgers School of Public Health4;Tobacco Research Programs5; Department of Psychiatry6

To investigate the potential effect on cigarette relighting on key chemical constituentsimplicated in addictiveness, toxicity, and carcinogenicity of tobacco and cigarette smoke.

INTRODUCTION

MASONIC CANCER CENTER, UNIVERSITY OF MINNESOTA, MINNEAPOLIS, MN 55455

REFERENCESSUMMARY

ACKNOWLEDGMENTS

METHODS

RESULTS

This study was supported by NCI through the NIH Tobacco Regulatory Science Program (R01-CA179246) and UMF0011369 from UMN. LC-MS/MS was carried out in the Analytical Biochemistry Shared Resource of the Cancer Center.We thank Bob Carlson for graphic design assistance

Nicotine levels in the filler of original and half-smoked cigarette

Difference in smoke nicotine levels between first and second cigarette halves

Difference in aldehyde levels between first and second cigarette halves

0.0

5.0

10.0

15.0

20.0

Marlboro Gold Marlboro Gold 100s Marlboro Menthol Marlboro Menthol100s

3R4F 1R5F

Nicotine Tobacco filler2nd half ISO2nd half CI

mg/

gr

TSNA levels in the filler of original and half-smoked cigarettes

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2

4

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10

MarlboroGold

MarlboroGold 100s

MarlboroMenthol

MarlboroMenthol

100s

3R4F 1R5F

ISO smoking regime 1st half

2nd half

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25

MarlboroGold

MarlboroGold 100s

MarlboroMenthol

MarlboroMenthol

100s

3R4F 1R5F

CI smoking regime 1st half2nd half

Total particulate matter (TPM) in the smoke of first and second cigarette halves

0%10%20%30%40%50%60%70%80%

MarlboroGold

MarlboroGold 100s

MarlboroMenthol

MarlboroMenthol

100s

3R4F 1R5F

NNN under ISO smoking regime

-10%0%

10%20%30%40%50%60%70%

MarlboroGold

MarlboroGold 100s

MarlboroMenthol

MarlboroMenthol

100s

3R4F 1R5F

NNK under ISO smoking regime

0%

10%

20%

30%

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50%

MarlboroGold

MarlboroGold 100s

MarlboroMenthol

MarlboroMenthol

100s

3R4F 1R5F

NNN under CI smoking regime

-40%-30%-20%-10%

0%10%20%30%40%50%

MarlboroGold

MarlboroGold 100s

MarlboroMenthol

MarlboroMenthol

100s

3R4F 1R5F

NNK under CI smoking regime

-15%-10%-5%0%5%

10%15%20%25%30%35%

Marlboro GoldMarlboro Gold100s

MarlboroMenthol

MarlboroMenthol 100s

3R4F 1R5F

ISO smoking regime

-40%

-20%

0%

20%

40%

60%

80%

MarlboroGold

MarlboroGold 100s

MarlboroMenthol

MarlboroMenthol 100s

3R4F 1R5F

CI smoking regime

0.0

0.5

1.0

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2.0

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MarlboroGold

MarlboroGold 100s

MarlboroMenthol

MarlboroMenthol 100s

3R4F 1R5F

NNNtobaccofiller

0

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1

1.5

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2.5

MarlboroGold

MarlboroGold 100s

MarlboroMenthol

MarlboroMenthol 100s

3R4F 1R5F

NNKtobacco filler

2nd half CI

ng/g

r

ng/g

r

mg/

cig

mg/

cig

• Overall, there was an increase in nicotine in the left over tobacco filler of half-smoked cigarette using ISO

and CI smoking regimens• Levels of tobacco specific nitrosamines (NNN, NNK) were higher in the leftover tobacco filler of half-

smoked cigarette under CI regime, on average, NNK increased by 38%. • Similarly, levels of nicotine and nitrosamines in smoke increased in the 2nd half of the cigarette smoked

under both regimens, ISO and CI • Generally, there was increase in aldehyde levels under both smoking regimens. On average, acetaldehyde,

respiratory toxicant and carcinogen, increased in the 2nd half of the cigarette smoke by 86% and 37% for ISO and CI respectively

• Re-lighting a cigarette might expose smokers to higher levels of nicotine and carcinogens than exposures from the first half of the same cigarette, potentially posing increased health risks

• Study on tobacco smoke toxicants and carcinogens exposure in smokers engaging in relighting behavior is underway

Alkaloids

Tobacco filler (200 mg)

Tobacco specific nitrosamines

Extraction (1 hour) 10 mM ammonium acetate

Internal standard• 13C6NNN; D4NNKPurification • ChemElut, Silica

Dilution Internal standard• D3Nicotine; D4 minor

alkaloids

Column• Zorbax SB C-18Mobile phase • A: 10mM NH4OAC • B: Methanol

Column• HypercarbMobile phase • A: 0.0% FA in NH4OAC • B: Methanol

LC-MS/MS

Filter pads

-50%0%

50%100%150%200%250%300%350%400%450%

Form

alde

hyde

Ace

tald

ehyd

e

Ace

tone

Acr

olei

n

Pro

pion

alde

hyde

Cro

tona

ldeh

yde

But

anon

e

But

yral

dehy

de

ISO smoking regime

Marlboro Gold Marlboro Gold 100s Marlboro Menthol Marlboro Menthol 100s 3R4F 1R5F

Findings from analysis of left over tobacco filler of half-smoked cigarette

Findings from analysis of smoke of re-lit cigarette

Smoke

Column• Phenomenex Luna C18(2)Mobile phase • A: Water:ACN:THF:IPA 59:30:10:1• B: Water:ACN:THF:IPA

35:65:1:1

• Derivatization with 15ml DNPH (2 impingers)• Determination with 1% Trizma

HPLC – UV

Aldehydes

Relighting – extinguishing, saving, and later relighting unfinished cigarette butts is prevalent behavior with 44-73% of current smokers reporting that they relight cigarettes, 17-21% of those say they relight ‘usually’ or ‘frequently.’1 Certain vulnerable populations such as racial/ethnic minorities, people of low socioeconomic status (SES), LGBT persons and those suffering from mental illness are disproportionately affected by tobacco-associated diseases and are more likely to engage in relighting behavior2.Variety of chemical and physical processes are occurring during cigarette combustion resulting with formation of complex smoke mixture. As smoke is drawn through tobacco a portion of the combusted tobacco constituents are deposited on the unheated tobacco at the proximal end of the cigarette3. Extinguishing and later relighting unfinished cigarette could contribute towards substantial changes in the chemistry of the tobacco and cigarette smoke. Therefore better understanding of the exposures to tobacco smoke toxicants and carcinogens from relit cigarettes and its implications for tobacco related disease is needed.

Addictive constituent Carcinogens Respiratory toxicants

Nicotine

1. Cunningham JA, Selby P. Relighting cigarettes: how common is it? Nicotine Tob Res. 2007;9(5):621-623.

2. Kaufman, Annette R. “Cigarette Smoking Risk-Reducing Beliefs: Findings from the US Health Information Trends Survey.” Preventative Medicine, Science Direct, Sept. 2017,

3. Richard R. Baker,Product formation mechanisms inside a burning cigarette, Progress in Energy and Combustion Science, Volume 7, Issue 2,1981, Pages 135-153, ISSN 0360-1285

Difference in smoke TSNA levels between first and second cigarette halves %

cha

nge

in2nd

vs. 1

stha

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% c

hang

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2ndvs

. 1st

half

% c

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2ndvs

. 1st

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2ndvs

. 1st

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2ndvs

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2ndvs

. 1st

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% c

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2ndvs

. 1st

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2ndvs

. 1st

half

-100%

-50%

0%

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Form

alde

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Ace

tald

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Ace

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Acr

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Pro

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CI smoking regime

Marlboro Gold Marlboro Gold 100s Marlboro Menthol Marlboro Menthol 100s 3R4F 1R5F