those of ordinary skill in the art will realize that the following description of the present invention is illustrative only and not in any way limiting . other embodiments of the invention will readily suggest themselves to such skilled persons . the present invention is a method of stabilizing r - la . the method comprises the crystallization of r - la with nicotinamide . nicotinamide is a natural form of the vitamin niacin and thus , provides a stable crystalline form of r - la that is all natural . the amount of nicotinamide at non - toxic doses is about 20 milligrams ( mg ) to about 100 mg . the resulting product can be utilized alone , or in combination with vitamin supplements , food products , and the like . pharmaceutical compositions including the inventive combinations are also provided . the preparation of the pharmaceutical compositions of the invention is carried out in a known manner . useful carriers and auxiliaries for the inventive combinations include gelatin , natural sugars such as raw sugar or lactose , lecithin , pectin , starches ( e . g ., corn starch or amylose ), cyclodextrins and cyclodextrin derivatives , dextran , polyvinyl pyrrolidone , polyvinyl acetate , gum arabic , alginic acid , xylose , talcum , lycopodium , silica gel ( e . g ., colloidal silica gel ), cellulose , cellulose derivatives such as cellulose ethers ( e . g ., hpmc ), c 12 - 22 fatty acids and magnesium , calcium or aluminum salts thereof ( e . g ., stearates ), emulsifiers , oils and fats , in particular vegetable ( e . g ., peanut oil , castor oil , olive oil , sesame oil , cottonseed oil , corn oil , wheat germ oil , sunflower seed oil , cod liver oil ), glycerol esters and partial or complete polyglycerol esters of saturated fatty acids , pharmaceutically acceptably mono - or multivalent alcohols and polyglycols ( e . g ., polyethylene glycol and derivatives thereof ), esters of c 2 - 22 aliphatic saturated or unsaturated fatty acids ( preferably c 10 - 18 acids ) with monovalent c 1 - 20 aliphatic alcohols or multivalent alcohols such as glycols , glycerol , diethylene glycol , pentaerythritol , sorbitol , mannitol and the like ( which may optionally also be etherified ), esters of citric acid with primary alcohols , acetic acid , urea , benzyl benzoate , dioxolanes , glyceroforrnals , tetrahydrofurfuryl alcohol , polyglycol ethers with c 1 - 12 alcohols , dimethylacetamide , lactamides , lactates , ethylcarbonales , silicones ( e . g ., medium - viscosity polydimethyl siloxanes ), calcium carbonate , sodium carbonate , calcium phosphate , sodium phosphate , magnesium carbonate , etc . additional useful additives include disintegrants , such as cross - linked polyvinyl pyrrolidone , sodium carboxymethyl starch , sodium carboxymethyl cellulose or microcrystalline cellulose . the inventive combinations can be coated with conventional coating materials such as polymers and copolymers of acrylic acid and / or methacrylic acid and / or their esters ( e . g ., eudragit ® copolymers ), polyvinyl acetate , fats , oils , waxes , fatty alcohols , hydroxypropyl methyl cellulose phthalate or - acetate succinate , cellulose acetate phthalate , starch acetate phthalate , polyvinyl acetate phthalate , carboxy methyl cellulose , methyl cellulose phthalate , methyl cellulose succinate , zein , ethyl cellulose , ethyl cellulose succinate , shellac , gluten , ethylcarboxyethyl cellulose , ethacrylate - maleic acid anhydride copolymer , maleic acid anhydride - vinyl methyl ether copolymer , styrol - maleic acid copolymer , 2 - ethyl - hexyl - acrylate maleic acid anhydride , crotonic acid - vinyl acetate copolymer , glutaminic acid / glutamic acid ester copolymer , carboxymethylethyl - cellulose glycerol monooctanoate , cellulose acetate succinate , and polyarginin . useful plasticizing agents that can be used as coating materials include citric and tartaric acid esters ( acetyltriethyl citrate , acetyl tributyl -, tributyl -, triethyl - citrate ), glycerol and glycerol esters ( glycerol diacetate , - triacetate , acetylated monoglycerides , castor oil ), phthalic acid esters ( dibutyl -, diamyl -, diethyl -, dimethyl -, dipropyl - phthalate ), di -( 2 - methoxy - or 2 - ethoxyethyl )- phthalate , ethylphthalyl glycolate , butylphthalylethyl glycolate and butylglycolate ; alcohols ( propylene glycol , polyethylene glycol of various chain lengths ), adipates ( diethyladipate , di -( 2 - methoxy - or 2 - ethoxyethyl )- adipate , benzophenone ; diethyl - and dibutylsebacate , dibutylsuccinate , dibutyltartrate , diethylene glycol dipropionate , ethyleneglycol diacetate , - dibutyrate , - dipropionate , tributyl phosphate , tributyrin , polyethylene glycol sorbitan monooleate ( polysorbates such as polysorbate 80 ), and sorbitan monooleate . then the inventive combinations are solutions or suspensions , it is useful to employ solvents such as water or physiologically acceptable organic solvents including alcohols such as ethanol , propanol , isopropanol , 1 , 2 - propylene glycol , polyglycols and their derivatives , fatty alcohols , partial esters of glycerol , oils such as peanut oil , olive oil , sesame oil , almond oil , sunflower oil , soya bean oil , castor oil , bovine hoof oil , paraffins , dimethyl sulphoxide , triglycerides and the like . injectable solutions or suspensions including the inventive combinations can be prepared using non - toxic parenterally acceptable diluting agents or solvents , such as water , 1 , 3 - butanediol , ethanol , 1 , 2 - propylene glycol , polyglycols mixed with water , glycerol , ringer &# 39 ; s solution , isotonic salt solution or also hardened oils including synthetic mono - or diglycerides or fatty acids such as oleic acid . solubilizers and emulsifiers useful in preparing compositions according to the invention include polyvinyl pyrrolidone , sorbitan fatty acid esters such as sorbitan trioleate , phosphatides such as lecithin , acacia , tragacanth , polyoxyethylated sorbitan monooleate and other ethoxylated fatty acid esters of sorbitan , polyoxyethylated fats , polyoxyethylated oleotriglycerides , linolizated oleotriglycerides , polyethylene oxide condensation products of fatty alcohols , alkylphenols and fatty acids . for aqueous injection and drinkable solutions , the following stabilizers and solubilizers can be advantageously employed : c 2 - 4 aliphatic mono - and multivalent alcohols such as ethanol , n - propanol and glycerol , polyethylene glycols with molecular weights between 200 - 600 , diethylene glycol monoethyl ether , 1 , 2 - propylene glycol , organic amides ( e . g ., amides of aliphatic c 1 - 6 carboxylic acids with ammonia or primary , secondary or tertiary c 1 - 4 amines or c 1 - 4 hydroxy amines such as urea , urethane , acetamide , n - methyl acetamide , n , n - diethyl acetamide , n , n - dimethyl acetamide , c 2 - 6 aliphatic amines and diamines such as ethylene diamine , hydroxyethyl theophylline , tromethamine ( e . g ., as 0 . 1 to 20 % aqueous solution ), and aliphatic amino acids . preservatives , stabilizers , buffer substances , flavor correcting agents , sweeteners , colorants and antioxidants can also be employed . antioxidants can be employed as preservatives , but at higher concentrations antioxidants may serve as co - active ingredients with the inventive combinations ( i . e ., synergistic activity may occur ). useful antioxidants include sodium sulphite , sodium hydrogen sulphite , sodium metabisulphite , selenium , inorganic and organic selenium compounds and salts such as sodium selenite , ascorbic acid , ascorbyl palmitate , myristate and stearate , gallic acid , gallic acid alkyl ester , butylhydroxyanisol , nordihydroguaiacic acid and tocopherols , as well as synergists ( substances which bind heavy metals through complex formation , for example lecithin , ascorbic acid , phosphoric acid ethylene , diamine tetraacetic acid , citrates , and tartrates ). compositions including selenium salts such as sodium selenite may be beneficial . preservatives useful in the inventive compositions include , for example , sorbic acid , p - hydroxybenzoic acid esters , benzoic acid , sodium benzoate , trichloroisobutyl alcohol , phenol , cresol , benzethonium chloride , chlorhexidine and formalin derivatives . the pharmaceutical compositions may be applied to the skin or mucous membranes or to the inside of the body . application methods include but are not limited to , oral , enteral , pulmonal , nasal , lingual , intravenous , intra - arterial , intracardial , intramuscular , intraperitoneal , intracutaneous , subcutaneous and transdermal . the inventive compositions can also be formulated as cosmetic preparations , such as lotions , sun screens , ointments , solutions , creams , liposomes and emulsions . conventional cosmetic additives , carriers , etc . can be combined with the inventive compositions to produce the desired cosmetic preparations in accordance with methods known to those skilled in the art . tablet and capsule compositions of the invention advantageously include up to about 1000 mg of r - la and about 600 mg of nicotinamide . emulsions and liposomes advantageously include up to about 10 % ( w / v ) of r - la and 6 % of nicotinamide . micellar solutions beneficially contain up to about 20 wt % ( w / v ) of r - la and 12 % of nicotinamide . the exact dosage used will vary depending on the particular compound of the invention selected , the age , size , and health of the subject , and the nature and severity of the condition to be treated . however , the appropriate dosage may be determined by one of ordinary skill by routine experimentation , following the guidance set forth herein . as a general guideline , a compound of the invention may be administered daily in a dose of one or two tablets ( see below ) as a dietary supplement for aiding mitochondrial metabolism . suitable subjects include , without limitation , mammals , such as humans , horses , cattle , swine , dogs , cats , and the like , and cells in culture , including mammalian cells , yeast , bacterial cells and the like . a solution of 3 . 3 g of ( r )-(+)- α - lipoic acid in 20 ml methanol was added to a solution of 2 . 0 g nicotinamide ( sigma ) in 20 ml methanol . the mixture was stripped of solvent on the rotary evaporator to yield an off - white solid . this was triturated under 25 ml of anhydrous ether , stirred well and separated by filtration . there was obtained 3 . 1 g of a pale yellow crystalline powder . a small quantity of the powder as a mineral oil mull spread was spread on nacl polished crystal plates . the plate was placed in a beckman infrared spectrophotometer acculab 2 grating machine , linear in wave number . the results are shown in fig1 . spectrophotometry was repeated at about 3 and 17 months and was essentially the same , indicating essentially no change in either the crystal form or chemical composition of this salt on standing under ambient conditions ( light and temperature ) for over a year . content amount per % daily of tablet serving value sodium 3 mg & lt ; 1 nicotinamide 59 mg 300 r - α - lipoic acid 100 mg * acetyl - l - carnitine hcl 500 mg * ingredients include stearic acid , silicon dioxide , croscarmellose sodium , acacia , magnesium stearate and a white cellulose film coat containing titanium dioxide .
a method of stabilizing r - α - lipoic acid includes combining r - α - lipoic acid with nicotinamide in a weight ratio between about 10 : 4 to about 10 : 8 . a composition for treating oxidative stress includes r - α - lipoic acid and nicotinamide in a weight ratio of between about 10 : 4 and about 10 : 8 .