US20240130416A1 - Method for adjusting the nicotine content in an e-cigarette aerosol - Google Patents
Method for adjusting the nicotine content in an e-cigarette aerosol Download PDFInfo
- Publication number
- US20240130416A1 US20240130416A1 US18/257,735 US202118257735A US2024130416A1 US 20240130416 A1 US20240130416 A1 US 20240130416A1 US 202118257735 A US202118257735 A US 202118257735A US 2024130416 A1 US2024130416 A1 US 2024130416A1
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- US
- United States
- Prior art keywords
- nicotine
- liquid
- aerosol
- precursor substance
- inhaler
- 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.)
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 title claims abstract description 101
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title claims abstract description 100
- 229960002715 nicotine Drugs 0.000 title claims abstract description 100
- 239000000443 aerosol Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 31
- 239000003571 electronic cigarette Substances 0.000 title description 14
- 239000007788 liquid Substances 0.000 claims abstract description 79
- 239000000126 substance Substances 0.000 claims abstract description 53
- 239000002243 precursor Substances 0.000 claims abstract description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- 239000006200 vaporizer Substances 0.000 claims abstract description 19
- 230000008016 vaporization Effects 0.000 claims abstract description 11
- 239000000376 reactant Substances 0.000 claims description 27
- UIKROCXWUNQSPJ-VIFPVBQESA-N (-)-cotinine Chemical compound C1CC(=O)N(C)[C@@H]1C1=CC=CN=C1 UIKROCXWUNQSPJ-VIFPVBQESA-N 0.000 claims description 15
- UIKROCXWUNQSPJ-UHFFFAOYSA-N Cotinine Natural products C1CC(=O)N(C)C1C1=CC=CN=C1 UIKROCXWUNQSPJ-UHFFFAOYSA-N 0.000 claims description 15
- 229950006073 cotinine Drugs 0.000 claims description 15
- 238000006722 reduction reaction Methods 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- RWFBQHICRCUQJJ-NUHJPDEHSA-N (S)-nicotine N(1')-oxide Chemical compound C[N+]1([O-])CCC[C@H]1C1=CC=CN=C1 RWFBQHICRCUQJJ-NUHJPDEHSA-N 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- MYKUKUCHPMASKF-VIFPVBQESA-N (S)-nornicotine Chemical compound C1CCN[C@@H]1C1=CC=CN=C1 MYKUKUCHPMASKF-VIFPVBQESA-N 0.000 claims description 2
- MYKUKUCHPMASKF-UHFFFAOYSA-N Nornicotine Natural products C1CCNC1C1=CC=CN=C1 MYKUKUCHPMASKF-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 239000003638 chemical reducing agent Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000009834 vaporization Methods 0.000 description 5
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 241000208125 Nicotiana Species 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 235000019504 cigarettes Nutrition 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 239000003595 mist Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 235000019505 tobacco product Nutrition 0.000 description 2
- SAWAIULJDYFLPD-SOAFEQHCSA-N (S)-nicotinium N-alpha-D-glucosiduronate Chemical compound CN1CCC[C@H]1C1=CC=C[N+]([C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)=C1 SAWAIULJDYFLPD-SOAFEQHCSA-N 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 102000016397 Methyltransferase Human genes 0.000 description 1
- 108060004795 Methyltransferase Proteins 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- -1 zinc hydride complexes Chemical class 0.000 description 1
Images
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
- 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
- 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
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
- A24B15/283—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by encapsulation of the chemical substances
- A24B15/284—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by encapsulation of the chemical substances the additive being bound to a host by chemical, electrical or like forces, e.g. use of precursors, inclusion complexes
-
- 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
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
- A24B15/385—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom in a five-membered ring
-
- 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
-
- 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
- A24F40/30—Devices using two or more structurally separated inhalable precursors, e.g. using two liquid precursors in two cartridges
-
- 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
- A24F40/40—Constructional details, e.g. connection of cartridges and battery parts
Definitions
- the present invention relates to a method for adjusting the nicotine content of an aerosol in an inhaler, comprising the following steps:
- Inhalers particularly in the form of electronic cigarettes (hereinafter referred to as e-cigarettes) are used in the medical field and especially in the stimulants industry. E-cigarettes are enjoying great popularity and are increasingly replacing the use of conventional tobacco products. Unlike conventional tobacco products, in which the consumer inhales the smoke of burning plant parts, especially tobacco, no combustion of plant parts takes place in the e-cigarette. Instead, a fluid, usually referred to as liquid, is vaporized in a vaporizer unit and mixed with air in a flow channel, creating an aerosol, mist, or aerosol-vapor mixture that is inhaled by the consumer.
- a fluid usually referred to as liquid
- the liquid is stocked on or in the vaporizer cartridge.
- Various mixtures with different components of the same or different vapor densities are used as the liquid.
- a typical mixture for use in an e-cigarette has, for example, components of glycerin and propylene glycol, enriched by nicotine, optionally additionally with almost any flavoring.
- the nicotine content for the cigarette has a maximum value, there are maximum values of nicotine in the liquid for the content of nicotine of an e-cigarette, which must not be exceeded.
- the nicotine content of e-cigarette liquids is limited to a concentration of 20 mg/ml. According to 2014/40/EU, this limit only applies to liquids.
- the nicotine concentration of the aerosols produced during vaporization is not limited.
- the maximum permissible nicotine concentration in e-cigarette liquids in the EU is comparatively low.
- e-cigarette cartridges are sold that are filled with liquids containing 5% nicotine.
- the popularity and the tobacco cigarette-like experience that e-cigarette smokers find pleasant are due not only to the nicotine salts in the liquids sold in the U.S., but also to the high concentration, because this can achieve a rapid increase in blood nicotine concentration comparable to that of tobacco cigarettes. It is desirable to achieve a similar blood nicotine concentration also with e-cigarette liquids complying with the regulations in the EU.
- the task of the present invention is therefore to provide a method that enables an increased blood nicotine concentration to be achieved compared with that achievable with conventional liquids, while at the same time complying with the regulations of 2014/40/EU.
- This task is solved with a method of the kind mentioned at the beginning in that at least one of the at least one liquid has a precursor substance which can be converted into nicotine by chemical reaction, and the method further comprises a nicotine generation step in which the precursor substance is converted into nicotine by chemical reaction so that the final aerosol has a second nicotine content which is higher than the first nicotine content.
- the nicotine content in the generated aerosol by adding to the liquid at least one substance that is transformed into nicotine only in the course of the formation of the aerosol.
- the nicotine content of the liquid can be kept within the legally prescribed values, while at the same time the aerosol inhaled by the consumer has a higher nicotine content desired by the consumer.
- the precursor substance is converted during the process and further on in the process reaches the consumer in the aerosol as nicotine.
- aerosol refers to the vapor phase formed by vaporization of the liquid and is also intended to include mist, vapor or mixtures of aerosol, mist and/or vapor, i.e., the gaseous phase may contain solid and/or liquid particles.
- any chemical reactions are conceivable, substitutions, additions, eliminations, rearrangements, radical reactions or acid-base reactions.
- the chemical reaction is an oxidation or especially a reduction.
- a chemical reduction is the reverse reaction of an oxidation, in which a reducing agent donates electrons to an already oxidized substance (thus “reducing” it).
- the conversion of the precursor substance to nicotine occurs with the use of a catalyst.
- a catalyst enables conversions that would not be possible without the catalyst, or would be uneconomical, since, for example, too much energy would have to be supplied to initiate and/or carry out the reaction.
- the catalyst lowers the required activation energy by means of an intermediate reaction with the precursor substance.
- the reaction becomes more economical or even possible in the first place, because without the lowering, competing other reactions would take place that would not allow the actually desired reaction to occur or would do so only with very low yield.
- Enzymes are proteins that usually selectively catalyze a specific reaction. Enzymes can also allow the conversion reaction of the precursor substance to nicotine to proceed under mild conditions
- Nicotine has the following structural formula:
- nicotine glucuronide or nornicotine can be used as a precursor substance.
- the former can be converted into nicotine by means of ⁇ -glucurodnidase, in particular immobilized on a filter or a column, the latter by reaction with methyltransferase. Enzymes are therefore used here.
- the precursor substance cotinine or nicotine N′-oxide is particularly preferred. Both compounds can be converted to nicotine in a reduction reaction.
- Cotinine can be found as an alkaloid in tobacco plants. The structural formulas of cotinine and nicotine N′-oxide are shown below:
- the reduction of cotinine or nicotine N′-oxide is preferably carried out by catalytic hydrogenation, using lithium alanate (LiAlH 4 ) in polar protic solvents or using other zinc hydride complexes.
- the reduction can thus be accomplished under mild conditions.
- the precursor substance is preferably present in an amount such that a nicotine content of at least 30 mg/ml, preferably in particular at least 40 mg/ml and more preferably at least 50 mg/ml is obtained in the aerosol.
- the reactant may be present as a liquid in the liquid.
- the reactant can be a solid. It may either be inherently present as a solid or may have been converted to a solid by means of freeze-drying.
- the reactant is provided in a contact element, and in the nicotine production step the precursor substance is brought into contact with the reactant in the contact element.
- Filters are particularly suitable as such contact elements, as are grid structures. These are inserted into the air duct of an e-cigarette and, due to their large surface area, ensure intensive contact between the aerosol and, in particular, the precursor substance contained therein and the reactant contained in the filter.
- a preferred mode is to apply nanoparticles or microparticles in order to achieve the largest possible surface area.
- a spraying system is used to load the aerosol with the respective liquid reactant.
- An alternative preferred embodiment employs a filter and a semi-permeable membrane to ensure egress of the reactant into the aerosol channel while preventing entry of the aerosol into the filter.
- a pad impregnated with the liquid reactant can be placed in the air duct.
- the aerosol channel can be covered with the pad completely or partially, wherein any geometry can be used for the pad.
- a screen or grid can be used to absorb the liquid reactant. The sieve or grid is penetrated by the aerosol. In this way, the precursor substance to be reacted is reacted, with the increased surface area enabling particularly intensive contact between the reactant and the aerosol.
- attachments in the form of pads, grids or filters are so-called “disposables”, i.e. consumables that would have to be disposed of and replaced after a certain number of cycles because, for example in the case of reducing agents, the redox potential is no longer existent after a certain number of cycles.
- the number of puffs is recorded digitally and integrated into an app for controlling the e-cigarette. In this way, the consumer is reminded or made aware of how many puffs are still available and when it will be necessary to change the filter.
- the nicotine generation step can take place before the vaporization step, after the vaporization step, or simultaneously with the vaporization step.
- the nicotine precursor can first be converted to nicotine and then transferred to the aerosol phase along with the rest of the liquid.
- the conversion takes place during the formation of the aerosol.
- the conversion of the precursor substance to nicotine takes place in the aerosol phase.
- the process is carried out in an inhaler having a vaporizer tank with at least two vaporizer tank chambers, wherein each vaporizer tank chamber can be assigned its own vaporizer. In this way, it is possible to transfer different liquids with different ingredients separately to the aerosol phase.
- a first liquid may contain nicotine and the precursor substance may be contained either in the first liquid or in a second liquid.
- the precursor substance is contained in a second liquid.
- a first liquid contains nicotine and another liquid contains a reactant that causes the conversion of the precursor substance into nicotine.
- the first liquid may contain nicotine and the precursor substance, with the precursor substance reacting with the reaction agent only when the two liquids come together.
- the liquid containing nicotine and the precursor substance and the liquid containing the reaction agent are transferred to the aerosol phase separately.
- the reaction of precursor substance with the reactant to form nicotine then takes place in the aerosol phase when the two aerosols, i.e., the aerosols of the first and the further liquid are combined.
- the combination allows for the reaction of the precursor substance with the reactant to nicotine to occur.
- the final aerosol is formed having the second nicotine content, which is higher than the first nicotine content.
- the second liquid contains both, the precursor substance and the reactant.
- the reactant may be provided in the form of a filter in the air duct for the second aerosol and may convert the precursor substance as it passes through the filter in the aerosol.
- the liquid containing nicotine and the liquid containing the precursor substance and possibly the reactant are transferred separately to the aerosol phase.
- the reaction of precursor substance with reactant to form nicotine thus takes place separately. It is only after conversion of the precursor substance to nicotine that the aerosol containing the newly generated nicotine is combined with the aerosol of the liquid that already contained nicotine at the beginning.
- a three-tank system is used. This allows for the different substances to be stored separately from each other.
- a first tank would contain a conventional liquid with the basic nicotine content. This nicotine content would preferably correspond to the maximum permissible nicotine content.
- Another tank contains a liquid containing the precursor substance.
- a third tank contains a liquid containing the reactant and, if desired and/or required, a carrier substance.
- the usual carrier substances such as water, propylene glycol (PG) and/or glycerol, in particular vegetable glycerol (“vegan glycerols”—VG), are suitable as carrier substances.
- a first step the aerosol formation of the different liquids takes place.
- the precursor substance is first reacted separately with the reaction agent to form nicotine.
- the reaction agent for example, cotinine can first be reduced separately to nicotine, and it is avoided that other components of the liquid, such as flavors, are also reduced in an undesirable side reaction.
- a multi-chamber system also has several separate vaporizers.
- the aerosols are then mixed together to produce the final aerosol with increased nicotine content, which final aerosol is ultimately inhaled by the consumer.
- conversion of the precursor substance into nicotine takes place before a and/or between two e-cigarette sessions.
- the necessary amount of precursor substance is stored in converted form and/or kept in the aerosol phase by means of supplying heat until the consumer starts the next session. In this way, reactions that require more time and energy to take place and deliver enough nicotine molecules can also be used. If the next session is not started for a longer period of time, the heating is stopped so that no unintended reactions take place due to the advanced time.
- FIG. 1 is a schematic representation illustrating the steps of a first embodiment of the method according to the invention
- FIG. 2 is a schematic representation illustrating the steps of a second embodiment of the method according to the invention.
- FIGS. 3 a and 3 b are a schematic diagram illustrating the arrangement of a pad with reactant for carrying out the present invention.
- FIGS. 4 a and 4 b are a schematic illustration of the arrangement of a grid for absorbing reactant for carrying out the present invention.
- FIG. 1 shows a first vaporizer 1 in communication with a first tank 2 a and a second tank 2 b .
- the first tank 2 a contains a conventional liquid for an e-cigarette with a first nicotine content corresponding to the permissible nicotine content of 20 mg/ml, and with a certain content of cotinine.
- the second tank 2 b there is a second liquid containing a reducing agent in addition to a carrier.
- the two liquids are vaporized forming an aerosol.
- a first aerosol 3 a with conventional e-liquid and cotinine and a second aerosol 3 b with carrier and reducing agent are formed.
- Both aerosols 3 a , 3 b are used in contact with each other, whereby the reducing agent reduces the cotinine to nicotine, so that the content of nicotine in the aerosol increases.
- the final aerosol 4 is formed, which has a second nicotine content that is higher than the first nicotine content.
- FIG. 2 shows an embodiment with three different tanks 2 a , 2 b , 2 c , each of which is associated with a vaporizer 1 a , 1 b , 1 c .
- the first tank 2 a contains a conventional liquid with the basic nicotine content corresponding to the maximum permissible nicotine content of a liquid.
- a second tank 2 b contains a second liquid containing cotinine.
- the third tank 2 c contains a third liquid containing the reducing agent and PG as a carrier substance.
- a first aerosol 3 a containing nicotine and aroma, a second aerosol 3 b containing cotinine, and a third aerosol 3 c containing the reducing agent and PG are formed.
- second aerosol 3 b and third aerosol 3 c are mixed, and the cotinine contained in the second aerosol 3 b is reduced to nicotine with the reducing agent contained in third aerosol 3 c .
- the second and third aerosols 3 b , 3 c are still separated from the first aerosol 3 a . This prevents other components of the liquid, such as flavors, which are contained in the first aerosol 3 a together with the nicotine, from reacting uncontrollably with the reaction agent and also being reduced in an undesirable side reaction.
- the aerosols are then mixed together to produce the final aerosol 4 with increased nicotine content, which is ultimately inhaled by the consumer.
- FIG. 3 a shows an embodiment of an air duct 5 of an inhaler for carrying out the process according to the invention in side view
- FIG. 3 b shows the same air duct 5 in top view
- a filter 6 containing the nanoparticulate reducing agent is arranged in the air duct 5 .
- the aerosol 3 b containing cotinine passes through the filter 6 and thereby comes into contact with the reducing agent, so that the cotinine contained in the aerosol 3 b is reduced to nicotine.
- FIG. 4 a shows a further embodiment of an air duct 5 of an inhaler for carrying out the method according to the invention in side view
- FIG. 4 b shows the same air duct 5 in top view.
- a sieve or grid 7 is arranged in the air duct, in which the liquid reducing agent is accommodated. This sieve 7 is penetrated by the aerosol 3 b , whereby the contained cotinine to be reduced can extensively be reduced due to the increased surface area and, still contained in the aerosol 3 b , reaches the consumer as nicotine.
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Abstract
Description
- This application is the U.S. National Stage of PCT/EP2021/083732 filed on Dec. 1, 2021, which claims priority to German Patent Application 102020133733.7 filed on Dec. 16, 2020, the entire content of both are incorporated herein by reference in their entirety.
- The present invention relates to a method for adjusting the nicotine content of an aerosol in an inhaler, comprising the following steps:
-
- a feeding step in which at least one liquid having a first nicotine content is fed from a vaporizer tank to an electric vaporizer,
- a vaporizing step in which the at least one liquid is vaporized to produce an aerosol,
- a dispensing step in which a final aerosol consisting of the combination of all aerosols formed in the inhaler from the at least one liquid is dispensed from the inhaler to a user.
- Inhalers, particularly in the form of electronic cigarettes (hereinafter referred to as e-cigarettes) are used in the medical field and especially in the stimulants industry. E-cigarettes are enjoying great popularity and are increasingly replacing the use of conventional tobacco products. Unlike conventional tobacco products, in which the consumer inhales the smoke of burning plant parts, especially tobacco, no combustion of plant parts takes place in the e-cigarette. Instead, a fluid, usually referred to as liquid, is vaporized in a vaporizer unit and mixed with air in a flow channel, creating an aerosol, mist, or aerosol-vapor mixture that is inhaled by the consumer.
- The liquid is stocked on or in the vaporizer cartridge. Various mixtures with different components of the same or different vapor densities are used as the liquid. A typical mixture for use in an e-cigarette has, for example, components of glycerin and propylene glycol, enriched by nicotine, optionally additionally with almost any flavoring.
- As with conventional cigarettes the nicotine content for the cigarette has a maximum value, there are maximum values of nicotine in the liquid for the content of nicotine of an e-cigarette, which must not be exceeded. In the EU, for example, the nicotine content of e-cigarette liquids is limited to a concentration of 20 mg/ml. According to 2014/40/EU, this limit only applies to liquids. The nicotine concentration of the aerosols produced during vaporization is not limited.
- The maximum permissible nicotine concentration in e-cigarette liquids in the EU is comparatively low. In the USA, on the other hand, e-cigarette cartridges are sold that are filled with liquids containing 5% nicotine. The popularity and the tobacco cigarette-like experience that e-cigarette smokers find pleasant are due not only to the nicotine salts in the liquids sold in the U.S., but also to the high concentration, because this can achieve a rapid increase in blood nicotine concentration comparable to that of tobacco cigarettes. It is desirable to achieve a similar blood nicotine concentration also with e-cigarette liquids complying with the regulations in the EU.
- The task of the present invention is therefore to provide a method that enables an increased blood nicotine concentration to be achieved compared with that achievable with conventional liquids, while at the same time complying with the regulations of 2014/40/EU.
- This task is solved with a method of the kind mentioned at the beginning in that at least one of the at least one liquid has a precursor substance which can be converted into nicotine by chemical reaction, and the method further comprises a nicotine generation step in which the precursor substance is converted into nicotine by chemical reaction so that the final aerosol has a second nicotine content which is higher than the first nicotine content.
- In the context of the present invention, it has been found that it is possible to increase the nicotine content in the generated aerosol by adding to the liquid at least one substance that is transformed into nicotine only in the course of the formation of the aerosol. In this way, the nicotine content of the liquid can be kept within the legally prescribed values, while at the same time the aerosol inhaled by the consumer has a higher nicotine content desired by the consumer. The precursor substance is converted during the process and further on in the process reaches the consumer in the aerosol as nicotine.
- The term aerosol as used in the present invention refers to the vapor phase formed by vaporization of the liquid and is also intended to include mist, vapor or mixtures of aerosol, mist and/or vapor, i.e., the gaseous phase may contain solid and/or liquid particles.
- As chemical reaction by which the precursor substance is converted into nicotine, any chemical reactions are conceivable, substitutions, additions, eliminations, rearrangements, radical reactions or acid-base reactions. Particularly preferred, the chemical reaction is an oxidation or especially a reduction.
- A chemical reduction is the reverse reaction of an oxidation, in which a reducing agent donates electrons to an already oxidized substance (thus “reducing” it).
- Preferably, the conversion of the precursor substance to nicotine occurs with the use of a catalyst. The use of a catalyst enables conversions that would not be possible without the catalyst, or would be uneconomical, since, for example, too much energy would have to be supplied to initiate and/or carry out the reaction. The catalyst lowers the required activation energy by means of an intermediate reaction with the precursor substance. Thus, the reaction becomes more economical or even possible in the first place, because without the lowering, competing other reactions would take place that would not allow the actually desired reaction to occur or would do so only with very low yield.
- Furthermore, it is particularly preferred if the conversion of the precursor substance into nicotine is carried out using an enzyme. Enzymes are proteins that usually selectively catalyze a specific reaction. Enzymes can also allow the conversion reaction of the precursor substance to nicotine to proceed under mild conditions
- Nicotine has the following structural formula:
- Various compounds are conceivable as precursor substance. In an advantageous embodiment, nicotine glucuronide or nornicotine can be used as a precursor substance. The former can be converted into nicotine by means of β-glucurodnidase, in particular immobilized on a filter or a column, the latter by reaction with methyltransferase. Enzymes are therefore used here. The precursor substance cotinine or nicotine N′-oxide is particularly preferred. Both compounds can be converted to nicotine in a reduction reaction. Cotinine can be found as an alkaloid in tobacco plants. The structural formulas of cotinine and nicotine N′-oxide are shown below:
- Here, the reduction of cotinine or nicotine N′-oxide is preferably carried out by catalytic hydrogenation, using lithium alanate (LiAlH4) in polar protic solvents or using other zinc hydride complexes. The reduction can thus be accomplished under mild conditions.
- The precursor substance is preferably present in an amount such that a nicotine content of at least 30 mg/ml, preferably in particular at least 40 mg/ml and more preferably at least 50 mg/ml is obtained in the aerosol.
- With the present invention, it is also possible to use liquids that do not contain any nicotine at all, but only precursor substances, so that the entire nicotine is thus present only in the aerosol.
- The reactant may be present as a liquid in the liquid. Alternatively, the reactant can be a solid. It may either be inherently present as a solid or may have been converted to a solid by means of freeze-drying.
- In another particularly preferred embodiment, the reactant is provided in a contact element, and in the nicotine production step the precursor substance is brought into contact with the reactant in the contact element. Filters are particularly suitable as such contact elements, as are grid structures. These are inserted into the air duct of an e-cigarette and, due to their large surface area, ensure intensive contact between the aerosol and, in particular, the precursor substance contained therein and the reactant contained in the filter. For solid reactants or reactants solidified by means of lyophilization (freeze-drying), a preferred mode is to apply nanoparticles or microparticles in order to achieve the largest possible surface area.
- For liquid reactants, in a preferred embodiment a spraying system is used to load the aerosol with the respective liquid reactant. An alternative preferred embodiment employs a filter and a semi-permeable membrane to ensure egress of the reactant into the aerosol channel while preventing entry of the aerosol into the filter. Further alternatively, a pad impregnated with the liquid reactant can be placed in the air duct. In this case, the aerosol channel can be covered with the pad completely or partially, wherein any geometry can be used for the pad. Alternatively, a screen or grid can be used to absorb the liquid reactant. The sieve or grid is penetrated by the aerosol. In this way, the precursor substance to be reacted is reacted, with the increased surface area enabling particularly intensive contact between the reactant and the aerosol.
- The above-described attachments in the form of pads, grids or filters are so-called “disposables”, i.e. consumables that would have to be disposed of and replaced after a certain number of cycles because, for example in the case of reducing agents, the redox potential is no longer existent after a certain number of cycles. Preferably, the number of puffs is recorded digitally and integrated into an app for controlling the e-cigarette. In this way, the consumer is reminded or made aware of how many puffs are still available and when it will be necessary to change the filter.
- The nicotine generation step can take place before the vaporization step, after the vaporization step, or simultaneously with the vaporization step. Thus, the nicotine precursor can first be converted to nicotine and then transferred to the aerosol phase along with the rest of the liquid. Alternatively, the conversion takes place during the formation of the aerosol. Particularly preferably, the conversion of the precursor substance to nicotine takes place in the aerosol phase.
- Furthermore, it is particularly preferred if the process is carried out in an inhaler having a vaporizer tank with at least two vaporizer tank chambers, wherein each vaporizer tank chamber can be assigned its own vaporizer. In this way, it is possible to transfer different liquids with different ingredients separately to the aerosol phase.
- With such an embodiment with more than one vaporizer tank chamber, for example, working with several liquids is possible particularly well. Thus, a first liquid may contain nicotine and the precursor substance may be contained either in the first liquid or in a second liquid. Particularly preferably, the precursor substance is contained in a second liquid. In this way, the reaction to convert the precursor substance to nicotine can be carried out separately and there is no risk that the conversion reaction may cause undesirable reactions in the nicotine already present.
- Furthermore, it is preferred that at least two liquids are used, wherein a first liquid contains nicotine and another liquid contains a reactant that causes the conversion of the precursor substance into nicotine. The first liquid may contain nicotine and the precursor substance, with the precursor substance reacting with the reaction agent only when the two liquids come together.
- In this described variant, the liquid containing nicotine and the precursor substance and the liquid containing the reaction agent are transferred to the aerosol phase separately. The reaction of precursor substance with the reactant to form nicotine then takes place in the aerosol phase when the two aerosols, i.e., the aerosols of the first and the further liquid are combined. The combination allows for the reaction of the precursor substance with the reactant to nicotine to occur. The final aerosol is formed having the second nicotine content, which is higher than the first nicotine content.
- Thus, particularly preferably, the second liquid contains both, the precursor substance and the reactant. Alternatively, as described above, the reactant may be provided in the form of a filter in the air duct for the second aerosol and may convert the precursor substance as it passes through the filter in the aerosol.
- In the variant described above, the liquid containing nicotine and the liquid containing the precursor substance and possibly the reactant are transferred separately to the aerosol phase. The reaction of precursor substance with reactant to form nicotine thus takes place separately. It is only after conversion of the precursor substance to nicotine that the aerosol containing the newly generated nicotine is combined with the aerosol of the liquid that already contained nicotine at the beginning.
- In a preferred embodiment, a three-tank system is used. This allows for the different substances to be stored separately from each other. In such a case, a first tank would contain a conventional liquid with the basic nicotine content. This nicotine content would preferably correspond to the maximum permissible nicotine content. Another tank contains a liquid containing the precursor substance. Finally, a third tank contains a liquid containing the reactant and, if desired and/or required, a carrier substance. In particular, the usual carrier substances such as water, propylene glycol (PG) and/or glycerol, in particular vegetable glycerol (“vegan glycerols”—VG), are suitable as carrier substances.
- In a first step, the aerosol formation of the different liquids takes place. In a second step, the precursor substance is first reacted separately with the reaction agent to form nicotine. This avoids uncontrolled reaction of other components of the liquid with the reaction agent. For example, cotinine can first be reduced separately to nicotine, and it is avoided that other components of the liquid, such as flavors, are also reduced in an undesirable side reaction. Preferably, a multi-chamber system also has several separate vaporizers. In a third step, the aerosols are then mixed together to produce the final aerosol with increased nicotine content, which final aerosol is ultimately inhaled by the consumer.
- In another preferred embodiment, conversion of the precursor substance into nicotine takes place before a and/or between two e-cigarette sessions. The necessary amount of precursor substance is stored in converted form and/or kept in the aerosol phase by means of supplying heat until the consumer starts the next session. In this way, reactions that require more time and energy to take place and deliver enough nicotine molecules can also be used. If the next session is not started for a longer period of time, the heating is stopped so that no unintended reactions take place due to the advanced time.
- Further useful and/or advantageous features and embodiments of the method for adjusting the nicotine content of an aerosol in an inhaler are apparent from the description. Particularly preferred embodiments will be explained in more detail with reference to the accompanying drawing. In the drawing:
-
FIG. 1 is a schematic representation illustrating the steps of a first embodiment of the method according to the invention; -
FIG. 2 is a schematic representation illustrating the steps of a second embodiment of the method according to the invention; -
FIGS. 3 a and 3 b are a schematic diagram illustrating the arrangement of a pad with reactant for carrying out the present invention; and -
FIGS. 4 a and 4 b are a schematic illustration of the arrangement of a grid for absorbing reactant for carrying out the present invention. -
FIG. 1 shows afirst vaporizer 1 in communication with afirst tank 2 a and asecond tank 2 b. Thefirst tank 2 a contains a conventional liquid for an e-cigarette with a first nicotine content corresponding to the permissible nicotine content of 20 mg/ml, and with a certain content of cotinine. In thesecond tank 2 b there is a second liquid containing a reducing agent in addition to a carrier. The two liquids are vaporized forming an aerosol. Afirst aerosol 3 a with conventional e-liquid and cotinine and asecond aerosol 3 b with carrier and reducing agent are formed. Bothaerosols final aerosol 4 is formed, which has a second nicotine content that is higher than the first nicotine content. -
FIG. 2 shows an embodiment with threedifferent tanks vaporizer first tank 2 a contains a conventional liquid with the basic nicotine content corresponding to the maximum permissible nicotine content of a liquid. Asecond tank 2 b contains a second liquid containing cotinine. Finally, thethird tank 2 c contains a third liquid containing the reducing agent and PG as a carrier substance. - In a first step, the aerosol formation of the different liquids takes place. A
first aerosol 3 a containing nicotine and aroma, asecond aerosol 3 b containing cotinine, and athird aerosol 3 c containing the reducing agent and PG are formed. - In a second step,
second aerosol 3 b andthird aerosol 3 c are mixed, and the cotinine contained in thesecond aerosol 3 b is reduced to nicotine with the reducing agent contained inthird aerosol 3 c. During this process, the second andthird aerosols first aerosol 3 a. This prevents other components of the liquid, such as flavors, which are contained in thefirst aerosol 3 a together with the nicotine, from reacting uncontrollably with the reaction agent and also being reduced in an undesirable side reaction. - In a third step, the aerosols are then mixed together to produce the
final aerosol 4 with increased nicotine content, which is ultimately inhaled by the consumer. -
FIG. 3 a shows an embodiment of anair duct 5 of an inhaler for carrying out the process according to the invention in side view,FIG. 3 b shows thesame air duct 5 in top view. Afilter 6 containing the nanoparticulate reducing agent is arranged in theair duct 5. Theaerosol 3 b containing cotinine passes through thefilter 6 and thereby comes into contact with the reducing agent, so that the cotinine contained in theaerosol 3 b is reduced to nicotine. -
FIG. 4 a shows a further embodiment of anair duct 5 of an inhaler for carrying out the method according to the invention in side view,FIG. 4 b shows thesame air duct 5 in top view. A sieve orgrid 7 is arranged in the air duct, in which the liquid reducing agent is accommodated. Thissieve 7 is penetrated by theaerosol 3 b, whereby the contained cotinine to be reduced can extensively be reduced due to the increased surface area and, still contained in theaerosol 3 b, reaches the consumer as nicotine.
Claims (13)
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DE102020133733.7A DE102020133733B4 (en) | 2020-12-16 | 2020-12-16 | Method of adjusting the nicotine level in an e-cigarette aerosol |
DE102020133733.7 | 2020-12-16 | ||
PCT/EP2021/083732 WO2022128470A1 (en) | 2020-12-16 | 2021-12-01 | Method for adjusting the nicotine content in an e-cigarette aerosol |
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US20240130416A1 true US20240130416A1 (en) | 2024-04-25 |
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US18/257,735 Pending US20240130416A1 (en) | 2020-12-16 | 2021-12-01 | Method for adjusting the nicotine content in an e-cigarette aerosol |
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US (1) | US20240130416A1 (en) |
EP (1) | EP4262445A1 (en) |
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EP3148982A1 (en) * | 2014-05-27 | 2017-04-05 | R. J. Reynolds Tobacco Company | Nicotine salts, co-crystals, and salt co-crystal complexes |
US10172388B2 (en) | 2015-03-10 | 2019-01-08 | Rai Strategic Holdings, Inc. | Aerosol delivery device with microfluidic delivery component |
US20170112182A1 (en) * | 2015-10-23 | 2017-04-27 | Next Generation Labs, LLC | Nicotine composition for vaping devices and vaping devices employing the same |
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2020
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WO2022128470A1 (en) | 2022-06-23 |
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