|Publication number||US2981641 A|
|Publication date||Apr 25, 1961|
|Filing date||Jan 21, 1960|
|Priority date||Jan 21, 1960|
|Publication number||US 2981641 A, US 2981641A, US-A-2981641, US2981641 A, US2981641A|
|Inventors||O'neill Robert C|
|Original Assignee||Stauffer Chemical Co|
|Export Citation||BiBTeX, EndNote, RefMan|
|Non-Patent Citations (1), Referenced by (17), Classifications (8)|
|External Links: USPTO, USPTO Assignment, Espacenet|
TOBACCO PRODUCTS Robert C. ONeill, New York, N.Y., assignor to Stauifer Chemical Company, New York, N.Y., a corporation of Delaware No Drawing. Filed Jan. 21, 1960, Ser. No. 3,718
7 Claims. (Cl. 131-17) The present invention is concerned with treated tobacco products. In particular, it deals with tobacco in which there has been incorporated a compound which is an antagonist for nicotine and which has a particular chemical structure.
The compounds useful in the present invention as antagonists for nicotine are chemically related to nicotine itself,- but they differ from nicotine in that the methyl group present on the nitrogen atom in the -membered ring of nicotine has been replaced by a lower alkyl group containing from 2 to 8 carbon atoms. As examples of suitable alkyl groups there may be mentioned the ethyl group, the propyl group, the isopropyl group, the hexyl group, the isobutyl group, the octyl group and the allyl group.
The antagonist may be used in the form of a free base, but it is preferred to use it in the form of a salt of an acid. It is most preferred to use the antagonist as the salt of an organic acid, particularly an organic acid which naturally forms salts with nicotine in tobacco, e.g. citric acid and malic acid.
Many persons who smoke desire to break the smoking habit. The reasons for desiring to break the habit are many and varied, and may be based on advice from a physician or purely on economic considerations. In any case it has been the experience of numerous smokers, and particularly of very heavy smokers, that it is very difficult to give up the tobacco habit.
The compositions of the present invention are useful in assisting a smoker to break the tobacco habit. Tobaccos treated in accordance with the present invention, when burned in accordance with usual smoking practice, yield a smoke which contains vapors of the compound which is antagonistic to nicotine. The smoke provides the desired aroma and taste of smoke from conventional tobacco, but because of the antagonistic action of the additives, the physiological responses elicited by nicotine and related alkaloids naturally in tobacco are diminished. This diminished physiological response helps the smoker to stop smoking or to reduce the smoking habit.
In accordance with the present invention the nicotine antagonist, which is in all cases a tertiary amine, is incorporated in the tobacco, preferably in the form of a salt with an organic acid with naturally occurs with nicotine in tobacco, for example citric and malic acids. A solution of the salt is sprayed on the tobacco prior to the final processing steps in which it is made into the usual forms such as cigarettes, cigars and pipe tobacco. The amount of antagonist to be incorporated in the tobacco is preferably of the same order of magnitude as the amount of nicotine present in the tobacco. Information pnblished in the scientific literature indicates that the amount of nicotine present in tobacco varies from 0.5 to 8.0%. In the case of cigarette tobacco, the usual range is from 0.7 to 3.0%, with about 1.5% being an average value.
United ntates Patent The N-alkyl nornicotine compounds of the present invention are prepared by the reaction of nornicotine, which occurs naturally in tobacco, and the appropriate alkyl halide. The acid addition salts are prepared by simple reaction between the free base and an acid, for example, acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, citric acid and malic acid.
The following examples are given solely for the purposes of illustration and are not to be considered limitations of the invention, many variations of which will occur to those skilled in the art without departing from the spirit or scope thereof.
Example 1 Tobacco leaves are sprayed with an aqueous solution of the citrate salt of N-allyl nornicotine, so that after drying, the tobacco contains 3% of the added material. The spraying operation is conducted so that the additive is uniformly distributed throughout the tobacco mass. The tobacco is then processed in the normal fashion, and made into cigarettes, cigars or pipe tobacco as desired.
Smokers who substitute tobacco treated in accordance with the present invention for their normal conventional cigars, pipes or cigarettes experience the same desirable taste as with conventional tobacco, but also experience a decrease in the craving for tobacco. The subjects find that less will power is required in order to decrease or completely eliminate the smoking habit.
Example 2 The procedure of Example 1 may be repeated except that in place of the citrate salt, the malic acid salt is used. In like manner, when in place of N-allyl nornicotine, N-ethyl nornicotine, Nhexyl nornicotine or N-octyl nornicotine is used, either in the form of the free base or an acid addition salt, similar results are obtained. The concentration of the additive may be varied from 0.5 to 8.0%.
What is claimed is:
1. As a novel composition of matter, tobacco comprising from 0.5 to 8.0% of a compound selected from the group consisting of N-alkyl nornicotine compounds containing from 2 to 8 carbon atoms in the alkyl group, and acid addition salts thereof.
2. As a novel composition of matter, tobacco comprising from 0.5 to 8.0% of an N-alkyl nornicotine compound containing from 2 to 8 carbon atoms in the alkyl group, said compound being present in the form of a salt of an organic acid which naturally forms a salt with nicotine in tobacco.
3. As a novel composition of matter, tobacco comprising from 0.5 to 8.0% of N-allyl nornicotine in the form of a salt of an organic acid which naturally forms a salt with nicotine in tobacco.
4. As a novel composition of matter, tobacco comprising from 0.7 to 3.0% of an N-alkyl nornicotine compound containing from 2 to 8 carbon atoms in the alkyl group, said compound being present in the form of a salt of an organic acid which naturally forms a salt with nicotine in tobacco.
5. As a novel composition of matter, tobacco comprising from 0.7 to 3.0% of N-allyl nornicotine in the form of a salt of an organic acid which naturally'forms a salt with nicotine in tobacco.
6. As a novel composition of matter, tobacco comprising from 0.5 to 8.0% of N-allyl nornicotine citrate.
7. As a novel composition of matter, tobacco comprising from 0.7 to 3.0% of N-allyl nornicotine citrate.
No references cited.
|Citing Patent||Filing date||Publication date||Applicant||Title|
|US3071509 *||Mar 9, 1961||Jan 1, 1963||Stauffer Chemical Co||N-alkyl-nornicotine:nicotine antagonist|
|US4765348 *||Dec 12, 1986||Aug 23, 1988||Brown & Williamson Tobacco Corporation||Non-combustible simulated cigarette device|
|US5316759 *||Mar 23, 1992||May 31, 1994||Robert J. Schaap||Agonist-antagonist combination to reduce the use of nicotine and other drugs|
|US5574052 *||Apr 29, 1994||Nov 12, 1996||Robert J. Schaap||Agonist-antagonist combination to reduce the use of nicotine and other drugs|
|US5596007 *||May 18, 1992||Jan 21, 1997||Pharmaco Behavioral Associates, Inc.||Therapeutic method to alleviate the craving associated with cessation of tobacco with cotinine|
|US5612357 *||Aug 22, 1994||Mar 18, 1997||Pharmaco Behavioral Associates, Inc.||Use of cotinine to assist in the cessation of tobacco smoking|
|US5880164 *||Oct 3, 1996||Mar 9, 1999||Lectec Corporation||Nicotine-free smoking material|
|US5935975 *||Apr 30, 1993||Aug 10, 1999||Robert J. Schaap||Agonist-antagonist combination to reduce the use of nicotine and other drugs|
|US7682633||Mar 6, 2009||Mar 23, 2010||Alpharma Pharmaceuticals, Llc||Pharmaceutical composition|
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|US8623418||Dec 16, 2008||Jan 7, 2014||Alpharma Pharmaceuticals Llc||Pharmaceutical composition|
|US8685443||Apr 23, 2010||Apr 1, 2014||Alpharma Pharmaceuticals Llc||Sequestering subunit and related compositions and methods|
|US8685444||Apr 23, 2010||Apr 1, 2014||Alpharma Pharmaceuticals Llc||Sequestering subunit and related compositions and methods|
|US8846104||Feb 13, 2012||Sep 30, 2014||Alpharma Pharmaceuticals Llc||Pharmaceutical compositions for the deterrence and/or prevention of abuse|
|US8877247||Feb 22, 2010||Nov 4, 2014||Alpharma Pharmaceuticals Llc||Abuse-deterrent multi-layer pharmaceutical composition comprising an opioid antagonist and an opioid agonist|
|WO1996027303A1 *||Mar 4, 1996||Sep 12, 1996||Lectec Corp||Nicotine-free smoking material|
|U.S. Classification||131/352, 546/276.4, 131/270, 514/343|
|International Classification||A24B15/38, A24B15/00|