Anatabine-Enriched Tobacco Products

Abstract

A tobacco product contains tobacco material enriched with anatabine or a salt or derivative thereof. In some aspects, the tobacco material has very low levels of tobacco specific nitrosamines (TSNA), such as having a collective content of N′-nitrosonornicotine (NNN), 4-(N-nitrosomethylamino)-1-(3-pyridyl)-1-butanone (NNK), N′-nitrosoanatabine (NAT) and N′-nitrosoanabasine (NAB) which is about 0.3 μg/g or less. The tobacco product may be a smoking product, such as cigarettes, cigars, or pipe tobacco; or a smokeless product, such as chewing tobacco, snuff, snus, tobacco-containing gum or lozenges, or a dissolvable powdered tobacco-based smokeless product.

1 . A tobacco product comprising tobacco material enriched with a compound of Formula I or a salt thereof: 
       
         
           
           
               
               
           
         
       
       wherein:
 R represents hydrogen or C 1 -C 5  alkyl; 
 R′ represents hydrogen or C 1 -C 7  alkyl; 
 X represents halogen or C 1 -C 7  alkyl; 
 the dotted line within the piperidine ring represents a carbon/carbon or carbon/nitrogen double bond within that ring, or two conjugated double bonds within that ring; wherein one of the two conjugated double bonds is a carbon/nitrogen double bond, or both of the conjugated double bonds are carbon/carbon double bonds; wherein when a carbon/nitrogen double bond is present, R is absent; and either (i) “a” is an integer ranging from 1-4 and “b” is an integer ranging from 0-8; or (ii) “a” is an integer ranging from 0-4 and “b” is an integer ranging from 1-8; and wherein when a carbon/nitrogen double bond is not present, R is present; “a” is an integer ranging from 0-4; and “b” is an integer ranging from 0-8. 
 
     
     
         2 . The tobacco product of  claim 1 , wherein the tobacco material has a collective content of N′-nitrosonornicotine (NNN), 4-(N-nitrosomethylamino)-1-(3-pyridyl)-1-butanone (NNK), N′-nitrosoanatabine (NAT) and N′-nitrosoanabasine (NAB) which is 0.3 μg/g or less. 
     
     
         3 . The tobacco product of  claim 1  wherein the collective content is 0.2 μg/g or less. 
     
     
         4 . The tobacco product of  claim 4  wherein the collective content is 0.1 μg/g or less. 
     
     
         5 . A tobacco product of  claim 1  wherein the content of 4-(N-nitrosomethylamino)-1-(3-pyridyl)-1-butanone (NNK) is 0.05 μg/g or less. 
     
     
         6 . The tobacco product of  claim 5  wherein the content of 4-(N-nitrosomethylamino)-1-(3-pyridyl)-1-butanone (NNK) is 0.01 μg/g or less. 
     
     
         7 . The tobacco product of  claim 1  wherein the tobacco material consists essentially of Virginia flue cured tobacco. 
     
     
         8 . The tobacco product of  claim 1  wherein the compound of Formula I is anatabine or a salt thereof. 
     
     
         9 . The tobacco product of  claim 8  wherein anatabine or a salt thereof is present in an amount of about 0.1 wt. % to about 10 wt. % above the anatabine content in the tobacco material, based on the total weight of the tobacco material. 
     
     
         10 . The tobacco product of  claim 9 , wherein anatabine or a salt thereof is present in an amount of about 0.5 wt. % to about 5 wt. % above the anatabine content in the tobacco material, based on the total weight of the tobacco material. 
     
     
         11 . The tobacco product of  claim 1  which is a smoking product selected from the group consisting of cigarettes, cigars, and pipe tobacco. 
     
     
         12 . The tobacco product of  claim 11  which is a cigarette. 
     
     
         13 . The tobacco product of  claim 1  which is a smokeless product selected from the group consisting of chewing tobacco, snuff, snus, tobacco-containing gum or lozenges, and dissolvable powdered tobacco-based smokeless products. 
     
     
         14 . The tobacco product of  claim 13  which is a dissolvable powdered tobacco-based smokeless product. 
     
     
         15 . The tobacco product of  claim 1  wherein the tobacco materially is partially denicotinized. 
     
     
         16 . The tobacco product of  claim 1  wherein the tobacco materially is wholly denicotinized. 
     
     
         17 . The tobacco product of  claim 1  wherein the tobacco material is further enriched with a compound selected from the group consisting of nornicotine, anabasine, and combinations thereof.