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US3071509A - N-alkyl-nornicotine:nicotine antagonist - Google Patents

N-alkyl-nornicotine:nicotine antagonist
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US3071509A
US3071509AUS94446AUS9444661AUS3071509AUS 3071509 AUS3071509 AUS 3071509AUS 94446 AUS94446 AUS 94446AUS 9444661 AUS9444661 AUS 9444661AUS 3071509 AUS3071509 AUS 3071509A
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United States
Prior art keywords
alkyl
nicotine
nornicotine
mgm
antagonist
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US94446A
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Robert C O'neill
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Stauffer Chemical Co
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Stauffer Chemical Co
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Priority to US94446ApriorityCriticalpatent/US3071509A/en
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United States Patent Ofifice Patented Jan. 1, 1963 3,071,509 N-Atkrt-Noarstcornsnuutcornsn ANrAooNisr No Drawing. Filed Mar. 9, 1961, Ser. No. 94,446 4 flaims. (Cl. 167-55) The present invention is concerned with certain novel pharmaceutical dosage forms. In particular, it is concerned with unitary dosage forms of certain compounds which I have found exert a physiological response antagonistic to that of nicotine.
The present application is a continuation in part of my copending application Serial Number 3,718, filed on January 21, 1960, noW Patent No. 2,981,641.
Many persons who smoke tobacco desire to break the smoking habit, or at least to diminish the amount of smoking. The reasons for such desire are many and varied, any 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. There are also many persons upon whom the nicotine absorbed from smoked tobacco exerts an undesired effect, for example, upon blood pressure or gastric secretion.
The present invention provides a help to the solution of the above problems. According to the present invention, the smoker orally ingests a unitary dosage form of a nicotine antagonist.
The nicotine antagonists useful in the present invention are compounds which are chemically related to nicotine itself, but they differ from nicotine in that the methyl group present on the nitrogen atom in the 5- membered ring of nicotine has been replaced by a lower alkyl group containing from 2 to 8 carbon atoms. The compounds are, chemically, N-alkyl nornicotines. As examples of suitable alkyl groups, there may be mentioned ethyl, propyl, isopropyl, hexyl, isobutyl, octyl, and, preferably, allyl, which is an unsaturated alkyl group.
The antagonist may be used in the form of thefree base, but it is preferred to use it in the form of an acid addition salt. The salt may be of any non-toxic acid, for example, citric acid, m-alic acid, acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, and the like.
When taken by the smoker, the nicotine antagonists of the present invention diminish the physiological responses elicited in the smoker by nicotine and the related alkaloids absorbed from the smoke.
On the average, about 3 to 4 mgm. of nicotine are absorbed from the puffed smoke of an average cigarette. The smoke of a 10 gram cigar may contain some to more than 40 mgm. of nicotine. (See Goodman and Gilman, The Pharmacological Basis of Therapeutics, 2nd Edition, 1956, p. 624.) The dosage of the antagonist should be of approximately the same order of magnitude as the amount of nicotine absorbed by the smoker. For the majority of smokers, the daily dosage will be from about 5 mgm. to about 250 mgrn. Particularly in the case of dosages toward the upper end of this range, the antagonist is preferably taken in split dosages, say three or four a day. Most desirably, the dosage is taken in the form of a sustained release capsule or tablet.
The unitary dosage forms of the present invention may be formulated in accordance with conventional practices well-known in the art. Any compatible inert excipient may be used. Examples include starch, milk sugar, calcium phosphate and the like. The preparation of sustained release dosage forms is also a well developed art, and such forms of the antagonist may be prepared in accordance With Well-known methods.
Example I Fifty mgm. of the citrate salt of N-alkyl nornicotine is mixed with 200 mgm. of starch, and the mixture is pressed into a tablet. One such tablet is taken at each of 3 meals daily by a smoker who averages forty cigarettes a day. The usual physiological responses due to smoking are diminished, and the craving for tobacco is decreased.
The foregoing example is given solely for the purposes of illustration and is not to be construed as limitation of the invention, many variations of which will occur to those skilled in the art Without departing from the spirit or scope thereof.
What is claimed is:
1. A unitary dosage form suitable for oral ingestion comprising from about 5 to about 250 mgm. of a compound selected from the group consisting of N-alkyl nornico-tine compounds containing from 2 to 8 carbon atoms in the alkyl group, and addition salts thereof with non-toxic acids, together with a carrier.
2. A sustained release unitary dosage form suitable for oral ingestion comprising from about 5 to about 250 mgm. 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 addition salts thereof with non-toxic acids.
3. A unitary dosage form suitable for oral ingestion, comprising from about 5 to about 250 mgm. of the citrate of N-allyl nornicotine together with a carrier.
4. A sustained release unitary dosage form suitable for oral ingestion comprising from about 5 to about 250 mgm. of the citrate of N-allyl nornico-tine.
References Cited in the file of this patent UNITED STATES PATENTS 2,981,641 ONeill Apr. 25, 1961

Claims (1)

1. A UNITARY DOSAGE FORM SUITABLE FOR ORAL INGESTION COMPRISING FROM ABOUT 5 TO ABOUT 250 MGM. 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 ADDITION SALTS THEREOF WITH NON-TOXIC ACIDS, TOGETHER WITH A CARRIER.
US94446A1961-03-091961-03-09N-alkyl-nornicotine:nicotine antagonistExpired - LifetimeUS3071509A (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US4574151A (en)*1982-08-201986-03-04Peter Robin Broughton LawrenceAmine salts and products containing them
US4806356A (en)*1983-06-291989-02-21Shaw Alec S WTobacco product
US5122366A (en)*1989-01-211992-06-16The Arab Pharmaceutical CompanyAntismoke mouth wash comprising silver nitrate and propylene glycol
US5316759A (en)*1986-03-171994-05-31Robert J. SchaapAgonist-antagonist combination to reduce the use of nicotine and other drugs
US20080221085A1 (en)*2004-07-152008-09-11Universite LavalNicotinic Receptor Agonists for the Treatment of Inflammatory Diseases
US20080233197A1 (en)*2006-06-192008-09-25Francis Joseph MatthewsPharmaceutical compositions
US20100151014A1 (en)*2008-12-162010-06-17Alpharma Pharmaceuticals, LlcPharmaceutical composition
US20100152221A1 (en)*2007-12-172010-06-17Alpharma Pharmaceuticals, LlcPharmaceutical composition
US20100266645A1 (en)*2007-12-172010-10-21Alfred LiangPharmaceutical compositions
US20110014280A1 (en)*2002-09-202011-01-20Garth BoehmSequestering subunit and related compositions and methods
US8557804B2 (en)2002-03-252013-10-15Universite LavalNicotinic receptor agonists for the treatment of inflammatory diseases

Citations (1)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US2981641A (en)*1960-01-211961-04-25Stauffer Chemical CoTobacco products

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US2981641A (en)*1960-01-211961-04-25Stauffer Chemical CoTobacco products

Cited By (26)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US4574151A (en)*1982-08-201986-03-04Peter Robin Broughton LawrenceAmine salts and products containing them
US4806356A (en)*1983-06-291989-02-21Shaw Alec S WTobacco product
US5316759A (en)*1986-03-171994-05-31Robert J. SchaapAgonist-antagonist combination to reduce the use of nicotine and other drugs
US5574052A (en)*1986-03-171996-11-12Robert J. SchaapAgonist-antagonist combination to reduce the use of nicotine and other drugs
US5935975A (en)*1986-03-171999-08-10Robert J. SchaapAgonist-antagonist combination to reduce the use of nicotine and other drugs
US5122366A (en)*1989-01-211992-06-16The Arab Pharmaceutical CompanyAntismoke mouth wash comprising silver nitrate and propylene glycol
US8557804B2 (en)2002-03-252013-10-15Universite LavalNicotinic receptor agonists for the treatment of inflammatory diseases
US8551983B2 (en)2002-03-252013-10-08Universite LavalNicotinic receptor agonists for the treatment of inflammatory diseases
US8685444B2 (en)2002-09-202014-04-01Alpharma Pharmaceuticals LlcSequestering subunit and related compositions and methods
US8685443B2 (en)2002-09-202014-04-01Alpharma Pharmaceuticals LlcSequestering subunit and related compositions and methods
US20110014280A1 (en)*2002-09-202011-01-20Garth BoehmSequestering subunit and related compositions and methods
US20110027455A1 (en)*2002-09-202011-02-03Garth BoehmSequestering subunit and related compositions and methods
US20080221085A1 (en)*2004-07-152008-09-11Universite LavalNicotinic Receptor Agonists for the Treatment of Inflammatory Diseases
US8039459B2 (en)2004-07-152011-10-18Universite LavalNicotinic receptor agonists for the treatment of inflammatory diseases
US8158156B2 (en)2006-06-192012-04-17Alpharma Pharmaceuticals, LlcAbuse-deterrent multi-layer pharmaceutical composition comprising an opioid antagonist and an opioid agonist
US20100143483A1 (en)*2006-06-192010-06-10Alpharma Pharmaceuticals, Llc.Pharmaceutical compositions
US7682633B2 (en)2006-06-192010-03-23Alpharma Pharmaceuticals, LlcPharmaceutical composition
US7682634B2 (en)2006-06-192010-03-23Alpharma Pharmaceuticals, LlcPharmaceutical compositions
US20090162450A1 (en)*2006-06-192009-06-25Alpharma Pharmaceuticals, Llc.Pharmaceutical composition
US20080233197A1 (en)*2006-06-192008-09-25Francis Joseph MatthewsPharmaceutical compositions
US8846104B2 (en)2006-06-192014-09-30Alpharma Pharmaceuticals LlcPharmaceutical compositions for the deterrence and/or prevention of abuse
US8877247B2 (en)2006-06-192014-11-04Alpharma Pharmaceuticals LlcAbuse-deterrent multi-layer pharmaceutical composition comprising an opioid antagonist and an opioid agonist
US20100266645A1 (en)*2007-12-172010-10-21Alfred LiangPharmaceutical compositions
US20100152221A1 (en)*2007-12-172010-06-17Alpharma Pharmaceuticals, LlcPharmaceutical composition
US8623418B2 (en)2007-12-172014-01-07Alpharma Pharmaceuticals LlcPharmaceutical composition
US20100151014A1 (en)*2008-12-162010-06-17Alpharma Pharmaceuticals, LlcPharmaceutical composition

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