WO2012177510A2 - Composition d'alcaloïdes pour cigarette électronique - Google Patents

Composition d'alcaloïdes pour cigarette électronique Download PDF

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Publication number
WO2012177510A2
WO2012177510A2 PCT/US2012/042710 US2012042710W WO2012177510A2 WO 2012177510 A2 WO2012177510 A2 WO 2012177510A2 US 2012042710 W US2012042710 W US 2012042710W WO 2012177510 A2 WO2012177510 A2 WO 2012177510A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
alkaloid
anatabine
weight
cigarette
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2012/042710
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English (en)
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WO2012177510A3 (fr
Inventor
Jonnie R. Williams
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Individual
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of WO2012177510A2 publication Critical patent/WO2012177510A2/fr
Publication of WO2012177510A3 publication Critical patent/WO2012177510A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24F—SMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F15/00—Receptacles or boxes specially adapted for cigars, cigarettes, simulated smoking devices or cigarettes therefor
    • A24F15/01—Receptacles or boxes specially adapted for cigars, cigarettes, simulated smoking devices or cigarettes therefor specially adapted for simulated smoking devices or cigarettes therefor
    • A24F15/015—Receptacles or boxes specially adapted for cigars, cigarettes, simulated smoking devices or cigarettes therefor specially adapted for simulated smoking devices or cigarettes therefor with means for refilling of liquid inhalable precursors
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24F—SMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F40/00—Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
    • A24F40/10—Devices using liquid inhalable precursors

Definitions

  • Embodiments of the present invention are directed to e-cigarettes, alkaloid compositions for e-cigarettes, and refilling cartridges for e-cigarettes containing certain alkaloid compositions.
  • a refilling cartridge for an e-cigarette contains a liquid alkaloid composition comprising a solvent and at least about 25 wt.% anatabine based on the total alkaloid weight of the composition.
  • a kit for refilling an e-cigarette comprises (i) a liquid alkaloid composition comprising a solvent and at least about 25 wt.% anatabine based on the total alkaloid weight of the composition, and (ii) instructions for filling the liquid alkaloid composition into a liquid receptacle of an e-cigarette.
  • a method of refilling an e-cigarette includes the steps of (i) providing a liquid alkaloid composition comprising a solvent and at least about 25 wt.% anatabine based on the total alkaloid weight of the composition, and (ii) filling the liquid alkaloid composition into a liquid receptacle of an e- cigarette.
  • an e-cigarette comprises a cartridge containing a liquid alkaloid composition comprising a solvent and at least about 25 wt.% anatabine based on the total alkaloid weight of the composition.
  • the e- cigarette may be of a single-use or disposable type, or may be refillable with liquid alkaloid compositions to facilitate reuse.
  • non-tobacco products that contain an alkaloid composition comprising about 25 wt.% to about 95 wt.% anatabine, and about 5 wt.% to about 75 wt.% of a second alkaloid, based on the total alkaloid weight of the composition.
  • the second alkaloid may be nicotine, nornicotine, anabasine, or a combination of two or more of them.
  • the non-tobacco product may be in the form of a solid bit of compressed powder, chewing gum, gelcap, capsule, pill, lozenge, or the like.
  • the alkaloid compositions disclosed herein feature different ranges of alkaloids to provide an attractive alternative to smoking conventional e- cigarettes, in which nicotine makes up about 90 to 100 wt.% of the total alkaloid content.
  • the disclosed alkaloid compositions are characterized by a significant quantity of anatabine, which has lower toxicity and risk of abuse as compared to other alkaloids such as nicotine.
  • the alkaloid compositions enable individuals to experience the pleasure-enhancing attributes of conventional cigarette smoking, while avoiding exposure to combusted materials and other potentially hazardous components present in tobacco. As a result, individuals may be more likely to quit conventional cigarette smoking.
  • FIG. 1 is a schematic illustration of one example of an e-cigarette configuration.
  • Tobacco is among the most chemically complex substances known, with tobacco and tobacco smoke containing more than 8,000 compounds.
  • tobacco contains the minor alkaloids nornicotine, anabasine, and anatabine.
  • nicotine is regarded as the principal addictive component in tobacco, a variety of other factors also are believed to contribute to tobacco addiction.
  • tobacco smoke has been reported to have a monoamine oxidase (MAO) inhibitory effect.
  • MAO is an enzyme involved in the breakdown of dopamine, a pleasure-enhancing neurotransmitter. See J.S. Fowler et al, "Inhibition of Monoamine Oxidase B in the Brain of Smokers," Nature (Lond), 379(6567):733 736 (1996); J.
  • aspects of the present invention are directed to alkaloid compositions for e- cigarettes which are designed to provide different ranges of alkaloids to more effectively achieve the pleasure-enhancing effects that smokers obtain through smoking traditional cigarettes, while avoiding or reducing exposure to nicotine.
  • the alkaloid composition comprises at least about 25 wt. % anatabine based on the total alkaloid weight.
  • anatabine is the sole alkaloid present in the composition, e.g., anatabine comprises 100 wt.
  • anatabine and nicotine may be combined in a weight ratio (anatabine-to-nicotine) of about 50: 1 to about 1 :3, or from about 25: 1 to about 1 :2, from about 10: 1 to about 3:2, or from about 5: 1 to about 1 : 1.
  • Anatabine may be prepared synthetically, such as via a benzophenoneimine pathway as described in co-pending Application No. 12/729,346, filed March 23, 2010, the disclosure of which is incorporated herein by reference in its entirety.
  • Anatabine may be present in the form of a racemic mixture or as isolated enantiomer, e.g., R-(+)-anatabine or S-(-)-anatabine, and/or as one or more pharmaceutically acceptable (or food grade) salts of anatabine.
  • anatabine refers to racemic mixtures of anatabine, enantiomers of anatabine, salt and non-salt forms of anatabine, as well as salt and non-salt forms of anatabine enantiomers.
  • salts are described in P. H.
  • anatabine may be obtained by extraction from tobacco or other plants, such as members of the Solanaceae family, such as datura, mandrake, belladonna, capsicum, potato, tomato, nicotiana, eggplant, and petunia.
  • a tobacco extract may be prepared from cured tobacco stems, lamina, or both. Flue (bright) varieties of tobacco are often used, i.e., Virginia flue. Other tobacco varieties may be used, such as Burley, dark-fired, and/or other commercial tobacco varieties. Two or more tobacco varieties may be combined to form a blend.
  • cured tobacco material is extracted with a solvent, typically water, ethanol, steam, or carbon dioxide.
  • the resulting solution contains the soluble components of the tobacco, including alkaloids such as anatabine.
  • Anatabine may be purified using known techniques such as liquid chromatography.
  • the amount of anatabine present in the composition may vary depending on factors such as the type of e-cigarette and whether other active components, such as nicotine and/or other alkaloids, are present.
  • the amount of anatabine may range from about 0.1 to about 25 mg, from about 0.5 to about 20 mg, or from about 1 to about 10 mg, per total gram of composition.
  • compositions containing anatabine were found to be efficacious for the temporary reduction of tobacco cravings, even without the presence of nicotine.
  • Anatabine and other minor alkaloids also have been reported to bind to nicotinic receptors. See “Receptors for Nicotine in the Central Nervous System: 1 Radioligand Binding Studies,” Group Research & Development Centre, British-American Tobacco Co. Ltd. (1984).
  • the composition may contain up to about 75 wt.% of one or more other alkaloids, such as nicotine, nornicotine, and/or anabasine, based on the total alkaloid weight.
  • alkaloids may be extracted from tobacco or other plant materials and purified using known techniques, and/or prepared synthetically using known synthesis methods.
  • Anatabine and additional alkaloid(s), such as nicotine may be combined in a weight ratio (anatabine-to-total other alkaloids) of about 50: 1 to about 1 :3, or from about 25: 1 to about 1 :2, from about 10: 1 to about 3:2, or from about 5: 1 to about 1 : 1.
  • the composition typically contains other components such as water, organic solvents, sweetening and/or flavoring agents, and the like.
  • solvents that are commonly used in liquid compositions for e-cigarettes include polyhydric alcohols such as 1,2-propylene glycol (PG or MPG); monohydric alcohols such as ethanol; ethyl acetate; and the like.
  • the amount of water present typically ranges from about 0.1 to about 10 wt.%, usually from about 0.5 to about 5 wt.%.
  • the amount of organic solvent present typically ranges from about 50 to about 99 wt.%, often from about 75 to about 95 wt.%.
  • one or more flavorants may be added to the composition, non- limiting examples of which include peppermint, menthol, wintergreen, spearmint, propolis, eucalyptus, cinnamon, or the like.
  • the total amount of flavorants typically ranges from about 0.5 to about 15 wt.%, often from about 1 to about 10 wt.%, based on the total weight of the composition.
  • the e-cigarette may be of various types of configurations, the details of which form no part of the present invention.
  • e-cigarettes may be of a single-use or disposable type, or may be refillable with liquid alkaloid compositions and/or cartridges containing liquid compositions to facilitate reuse.
  • FIG. 1 An air inlet 4 is provided on the external wall of a shell 14 which houses LED 1, cell 2, electronic circuit board 3, normal pressure cavity 5, sensor 6, vapor-liquid separator 7, atomizer 9, liquid-supplying bottle 11, mouthpiece 15, microswitch 16, gas vent 17, and air passage 18.
  • the electronic circuit board 3 has an electronic switching circuit and a high frequency generator.
  • a negative pressure cavity 8 is provided in the sensor 6 and is separated from the sensor 6 by a ripple film.
  • An atomization cavity 10 is provided in the atomizer 9.
  • a retaining ring 13 is provided for locking the liquid-supplying bottle 1 1 between one side of the liquid-supplying bottle 1 1 and the shell 14; and an aerosol passage 12 is provided on the other side of the liquid-supplying bottle.
  • e-cigarettes that reduce cravings for traditional tobacco smoking, while minimizing toxicity and other undesirable side effects associated with nicotine and other tobacco components.
  • the e-cigarette may be used as needed to satisfy cravings, or at intervals such as once daily, twice daily, or three or more times daily, depending on such factors as the concentration of active components and the subject's physiological conditions.
  • a non-tobacco formulation contains an alkaloid composition comprising about 25 wt.% to about 95 wt.% anatabine, and about 5 wt.% to about 75 wt.% of a second alkaloid, based on the total alkaloid weight of the composition.
  • the second alkaloid may be nicotine, nornicotine, anabasine, or a combination of two or more of them.
  • the non-tobacco product may be in the form of a solid bit of compressed powder, chewing gum, capsule, pill, lozenge, or the like.
  • non-tobacco means that the product is essentially free of tobacco leaf or tobacco extract, except however that some or all of the alkaloids present in the non-tobacco product may be extracted from tobacco and purified using conventional techniques such as liquid chromatography. [25] Additional components ingredients may be added to the non-tobacco products to improve taste or stability.
  • Such additional components include, but are not limited to, sweeteners, natural flavorants, artificial flavorants, colorants, antioxidants, preservatives, chelating agents, viscomodulators, tonicifiers, odorants, opacifiers, suspending agents, binders, thickeners, and mixtures thereof, including, but not limited to, xanthum gum, carboxymethylcellulose, carboxyethylcellulose, hydroxypropylcellulose, methylcellulose, microcrystalline cellulose, starches, dextrins, fermented whey, tofu, maltodextrins, polyols (including sugar alcohols, such as sorbitol or mannitol), carbohydrates (e.g., lactose), propylene hlycol alginate, gellan gum, guar, pectin, tragacanth gum, gum acacia, locust bean gum, gum arabic, gelatin, mannitol, natural and/or artificial mint flavors, sucralose, silicon dioxide,
  • the non-tobacco products may be in a variety of forms, e.g., to be taken orally, such as pills, tablets, capsules, soft gels, gelcaps, liquids, syrups, suspensions, powders, chews, lozenges, gum, bars, etc., or to be administered by other routes, such as parenterally, by inhalation spray, topically, via an implanted reservoir, etc.
  • the alkaloid compositions also can be prepared to be administered in foods or beverages. For example, they can be supplied as a dried or powdered product for reconstitution with water or other suitable vehicle before use (e.g., milk, fruit juice, and the like).
  • Alkaloid compositions for e-cigarettes may be prepared by combining the components listed in Table 1 below and mixing to form a solution.
  • Anatabine may be prepared synthetically as described in Examples 1-3 of co-pending Application No. 12/729,346. Nicotine, anabasine, and nornicotine may be extracted from tobacco materials and purified using known techniques.
  • compositions described in Examples 1-8 may be filled into refilling cartridges for e-cigarettes, or filled into a liquid container that is used as part of a kit for refilling liquid receptacles in e-cigarettes.
  • the compositions alternatively may be filled into a single-use or disposable type of e-cigarette.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention porte sur une composition d'alcaloïdes pour une cigarette électronique contenant un solvant et au moins environ 25 % en poids d'anatabine, sur la base du poids total des alcaloïdes de la composition. La composition d'alcaloïdes peut être contenue dans une cartouche de recharge pour une cigarette électronique ou dans un récipient faisant partie d'un kit pour la recharge d'une cigarette électronique. Les compositions d'alcaloïdes selon la présente invention présentent une forme équilibrée d'alcaloïdes pour fournir une alternative intéressante à l'usage du tabac, dans lequel la nicotine représente environ 90 % en poids de la teneur totale en alcaloïdes. Les compositions d'alcaloïdes sont caractérisées par une quantité importante d'anatabine, qui a une plus faible toxicité que d'autres alcaloïdes tels que la nicotine. Les compositions d'alcaloïdes permettent à des individus de ressentir les attributs augmentant le plaisir de l'usage du tabac classique, tout en évitant l'exposition à des substances brûlées et d'autres constituants potentiellement dangereux présents dans le tabac.
PCT/US2012/042710 2011-06-23 2012-06-15 Composition d'alcaloïdes pour cigarette électronique Ceased WO2012177510A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161500237P 2011-06-23 2011-06-23
US61/500,237 2011-06-23

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WO2012177510A2 true WO2012177510A2 (fr) 2012-12-27
WO2012177510A3 WO2012177510A3 (fr) 2013-02-28

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