iStock_000004399118XSmall Toxines Created by Cooking

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Cooking Creates New Toxic Substances In FoodiStock_000002745567XSmall1
Adapted from ”New Substances In Prepared Food”ÇŁ by Wai Genriiu
See Footnotes for 135 scientific references!

Cooking food is always like doing a chemical experiment in high school. Due to heat, cooking or preparing food creates new substances. Most of these new substances come from proteins reacting with carbohydrates. Some of these substances cause cancer or brain diseases and impair neurotransmitter function and metabolism.

Many of these new substances are heterocyclic amines (HCA). Many of these HCA are directly or indirectly physically addictive.(1)   Due to the heat of cooking, these HCA originate from the interaction between protein and carbohydrates and / or creatine (in red meat) or nitrate (in vegetables). Some examples :

  • tryptophan + form- / acet-aldehyde  = 1-methyl-1,2,3,4-tetrahydro-beta-carboline (pro-mutagenic) (2)
  • tryptophan + glycolaldehyde  = 1-hydroxymethyl-tetrahydro-beta-carboline (3)
  • tryptophan + sugars (by freezing)  = 1,1'-ethyliden-ditryptofaan (very toxic) (4)
  • serotonine + formaldehyde   = 6-hydroxy-tetrahydro-beta-carboline (5)
  • serotonine + acetaldehyde  = 6-hydroxy-1-methyl-tetrahydro-beta-carboline (6)
  • tyramine + nitrite  = 3-diazotyramine(4-(2-aminoethyl))-6-diazo-2,4-cyclohexadienone (carcin.)(7)
  • salt + nitrite + protein / sugar  = 2-chloro-4-methylthiobutanoate (mutagenic) (8)
  • glutamate + sugars  = 2-amino-6-methyldipyrido-(1,2-a:3',2'-d)imidazole (carcinogenic) (9)
  • glutamate + sugars  = 2-aminodipyrido-(1,2-a:3',2'-d)imidazole (carcinogenic)(9)

When aldehydes react upon cyclic amino acids or -amines (like tryptophan, tryptamine, serotonine, phenylalanine, tyrosine, dopamine, tyramine, aniline), mostly beta-carbolines and isoquinolines originate. When creatinine (from meat) is involved, mostly imidazoquinolines and imidaziquinoxalines originate. (10) (Glutamate and tryptophan are amino acids, tyramine and serotonine are amines, and aldehydes are sugars)

In What Foods?

Almost all cooked or prepared foods contain:

  • 9H-pyrido(3,4-b)indole  = beta-carboline  = tryptophan / tryptamine + aldehydes (11)
  • 1-methyl-9H-pyrido(3,4-b)indole  = 1-methyl-beta-carboline  = tryptophan / tryptamine + aldehydes (11)

These substances influence benzodiazepine receptors in the brain, and indirectly lots of other neurotransmitters. (12) If these substances further react upon amines like aniline, they even become mutagenic (23). How much HCA originate depends on how much protein the food contains and on how much the food is heated. (14)   Because red meat contains both lots of protein and creatinine (creating creatine), prepared red meat contains the most HCA, especially when grilled (15). Besides prepared red meat, also prepared fish, soy and poultry contain lots of HCA. (16) Flavor-enhancers and bouillon contain protein-concentrates and therefore contain lots of HCA too. (11) But also prepared foods containing less protein contain HCA, like prepared grains (17) and -vegetables (18), and even foods like beer, soy sauce and canned orange juice. (19) For example:

Meat contains too much creatine (20):

  • 2-amino-1-methyl-6-(4-hydroxyfenyl)-imidazo-(4,5-b)pyridine (mutag.)  = creatine + tyrosine + glucose (21)

Soy contains globulins:

  • 2-amino-9H-pyrido(2,3-b)indole  (mutagenic) (22)  = soy-globulins + sugars (23)
  • 2-amino-3-methyl-9H-pyrido(2,3-b)indole (mutagenic) (24)  = soy-globulins + sugars (23)

Prepared fish contains (25):

  • 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole (mutagenic)(26)  = tryptophan + acetaldehyde (27)
  • 3-amino-1-methyl-5H-pyrido(4,3-b)indole (mutagenic)(26) = tryptophane + acetaldehyde (28)

Cooked Vegetables contain nitrite:

  • cancerous N-nitroso-compounds = amines + nitrite + sugars
  • specific N-nitroso-compound ;
  • 4-(2-aminoethyl)-6-diazo-2,4-cyclohexadienone (cancerous) = tyramine + nitrite + sugars (7)

Cooked Cabbages contain thiocyanates ;

  • toxic (29) tetrahydro-beta-carboline-derivates = isothiocyanate + tyramine / serotonine etc.

Cooked vegetables contain also flavonoids:

  • mutagenic glycosides (30)  = flavonods + heat

Canned orange juice contains free amino acids, which easily combine with aldehydes to create heterocyclic amines.

What Can HCA Do?

1. Act like Neurotransmitters

Some HCA, like beta-carbolines, can directly influence neurotransmitter-receptors, like benzodiazepine receptors. Simply because the body also composes beta-carbolines to function as neurotransmitters. HCA can also occupy receptors of other neurotransmitters, like serotonine- and dopamine receptors. Especially when they are composed of the same amines. Some examples ;

  • 3-methoxycarbonyl-beta-carboline acts through different receptors (31) and increases secretion and decomposition of dopamine, like physical stress does. (32) It enhances 'irrational' aggressive behaviour (33), and decreases social interaction (34).
  • 3-ethoxycarbonyl-beta-carboline, is hypnotic and anaesthetic (35), and inhibits investigative behaviour (36) and social interaction. (37) In dominant types it enhances aggressive behaviour, but inhibits sexual appetite. (38) It increases epinephrine-   (39) and cortisol-level, blood pressure and heart rate (40), and increases secretion and decomposition of dopamine (41), like physical stress does.
  • 3-Hydroxymethyl-beta-carboline ; though hypnotic (42), it negatively affects sleep (43).
  • 3-N-methylcarboxamide-beta-carboline enhances reckless- (44) and aggressive behaviour (45), and inhibits sexual appetite. (46) It generally inhibits (47), but locally stimulates norepinephrine secretion. (48) It increases glutamate- (49), ACTH- and Substance P-secretion (50), increases blood pressure (51) and though anaesthetic (52), causes physical stress. (53).
  • 3-Methylcarbonyl-6,7-dimethoxy-4-ethyl-beta-carboline blocks GABA receptors (54), increases GABA- and glycine-level, decreases glutamate- and aspartate-level (55), increases corticosterone-, epinephrine- and norepinephrine-secretion(56), decreases serotonine-secretion (57) and increases norepinephrine-receptor-activity. (58) It enhances the effect of cocaine (59), causes anxiety (60) and suppresses immune system activity. (61)
  • 3-Ethylcarbonyl-6-benzyloxy-4-methoxymethyl-beta-carboline is sedative (62), causes amnesia (63), and blocks beta-oestradiol-LH (lutinizing hormone) interaction. (64)
  • 3-Ethylcarbonyl-5-benzyloxy-4-methoxymethyl-beta-carboline strongly stimulates appetite. (65)
  • 3-Ethylcarbonyl-5-isopropyl-4-methyl-beta-carboline causes restlessness (66), sleeplessness (67), and decreases social interaction. (68)

Besides 'normal' beta-carbolines, prepared foods also contain tetrahydro-beta-carbolines. (69).

  • Tetrahydro-beta-carboline stimulates craving for alcohol (70), increases heart rate and blood pressure (71), and like 5-methoxy-tetrahydro-beta-carboline and 5-hydroxy-tetrahydro-beta-carboline increases prolactine-level and affects serotonine receptors. (72)
  • 6-methoxy-tetrahydro-beta-carboline increases norepinephrine- and ACTH- secretion, and decreases serotonine- and growth hormone secretion. (73)
  • 2-Fenylpyrazolo(4,3-c)quinoline-3(5H)-one is sedative (74), increases corticosterone-level (75) and decreases specific benzodiazepine-receptors in the brain. (76)

2. Cause Cancer

Part of the process causing cancer is mutagenic substances damaging cell-DNA. (see site5) Some HCA in prepared food are mutagenic.DNA-damage increases linearly with intake of HCA. (77) How cancerous HCA are is partly dependent on how much nitrogen they contain. (78) Salt, protein and nitrite (from vegetables) can supply nitrogen to react upon HCA. And nitrosated HCA are even more cancerous. (79) Some of the most widespread mutagenic HCA in prepared foods are:

  • pyridoindole (80) (amino-gamma-carboline)
  • 2-amino-9H-pyrido(2,3-b)indole(81) (amino-alpha-carboline)
  • 2-amino-3-methyl-9H-pyrido(2,3-b) (82)
  • 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole(83)
  • 3-amino-1-methyl-5H-pyrido(4,3-b)indole(84)
  • 1-methyl-3-carbonyl-1,2,3,4-tetrahydro-beta-carboline(85).
  • 4-aminobiphenyl(86)
  • 4,4'-methylenedianiline (87)
  • 3,2'-dimethyl-4-aminobiphenyl(88)
  • 1,2-dimethylhydrazine(89)
  • phenyl-hydroxylamine (90)
  • O-acetyl-N-(5-phenyl-2-pyridyl)-hydroxylamine(91)
  • 2-amino-3-methylimidazo(4,5-f)quinoline(92)
  • 2-amino-3-methylimidazo(4,5-f)quinoxaline(93)
  • 2-amino-3,4-dimethylimidazo(4,5-f)quinoline (94)
  • 2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline (95)
  • 2-amino-3,4,8-trimethylimidazo(4,5-b)pyridine(96)
  • 2-amino-3,4,8-trimethylimidazo(4,5-f)quinoxaline (97)
  • 2-amino-3,7,8-trimethylimidazo(4,5-f)-quinoxaline(98)
  • 2-amino-n,n,n-trimethylimidazo-pyridine(99)
  • 2-amino-n,n-dimethylimidazopyridine (100)
  • 2-amino-4-hydroxymethyl-3,8-dimethylimidazo-(4,5-g)-quinoxaline(101)
  • 2-amino-1,7,9-trimethylimidazo-(4,5-g)-quinoxaline (101)
  • 2-amino-1-methyl-6-phenylimidazo-(4,5-b)-pyridine(102)

3. Cause Brain Diseases

Some HCA are directly toxic to the brain, like common quinolines, which enter the brain through the dopamine-transport system. (103)  Other common HCA (like pyridines (104) and beta-carbolines (105)) only become toxic to the brain after they have been partly decomposed by different enzymes (106) in the body. Originally , these enzymes have to, and do protect the brain against toxic substances, but part of the HCA are accidentally transformed into more toxic substances. (107) Obviously nature didn't count on 'strange' HCA from prepared food. Pyridines can only occupy dopamine-receptors (108), and therefore are toxic to thesereceptors only. Partly decomposed pyridines are more toxic than the originals (109), but the originals do decrease dopamine- (110), norepinephrine- (111) and mostly serotonine-level (112). The destruction of receptors in the brain causes brain-diseases like AlzheimerÔÇ™s, ParkinsonÔÇ™s and schizophrenia. Some toxic-to-the brain HCA are:

  • 3-N-butylcarbonyl-beta-carboline (113)
  • 3-N-methylcarboxamide-beta-carboline(113)
  • 2-methyl-1,2,3,4-tetrahydro-beta-carboline(114)
  • 2-methyl-1,2,3,4-tetrahydro-isoquinoline(114)
  • quinolinate (115)
  • quisqualinate (116)
  • tetrahydroisoquinoline(117)
  • 1-benzyl-tetrahydro-isoquinoline(117)
  • N-methyl-(R)-salsolinol(118)
  • N-methyl-6-methoxy-1,2,3,4-tetrahydro-isoquinoline(119)
  • 6-methoxy-1,2,3,4-tetrahydro-isoquinoline(119)
  • 2,4,5-trihydroxyphenylalanine(120)
  • 6-hydroxy-dopamine(121)
  • N-methyl-4-fenyl-1,2,3,6-tetrahydropyridine(122)
  • 1-methyl-4-fenyl-1,2,3,6-tetrahydropyridine(123)
  • 1-methyl-4-fenyl-1,2,5,6-tetrahydropyridine(124).
  • 4-fenyl-1,2,3,6-tetrahydropyridine(125)
  • 4-fenylpyridine(125)
  • 3-acetylpyridine(126)
  • 1-methyl-4-phenyl-1,4-dihydropyridine(127)
  • 1-methyl-4-cyclohexic-1,2,3,6-tetrahydropyridine(128)
  • 1-methyl-4-(2'-methylfenyl)-1,2,3,6--tetrahydropyridine (129)
  • 1-methyl-4-(2'-ethylfenyl)-1,2,3,6-tetrahydropyridine (130)
  • 1-methyl-4-(3'-methoxyfenyl)-1,2,3,6-tetrahydropyridine(131)
  • 1-methyl-4-(methylpyrrol-2-yl)-1,2,3,6-tetrahydropyridine(132)

Though toxic pyridines create oxidative radicals (133) and decrease antioxidant-level (134), the intake of antioxidants cannot prevent brain damage by toxic pyridines. (135)

Additives

Food preparation is primarily there to make edible what is not so edible. Additives are primarily there to make fake food last longer, and to make you eat more. Taste enhancers for example are mostly concentrated protein, filled with lots of physical addictive beta-carbolines that make you eat more. Glutamate (popular in the Chinese kitchen) indirectly influences the same (Benzodiazepine) receptors.

Footnotes

Abstracts of most sources can be found at  the National Library of Medicine

(1) Loscher, W. et al, Withdrawal precipation by benzodiazepine receptor antagonists in dogs chronically treated with diazepam or the novel anxiolytic and anticonvulsant beta-carboline abecarnil. Naunyn Schmiedebergs Arch. Pharmacol. 1992 / 345 (4) / 452-460. , De Boer, S.F. et al, Common mechanisms underlying the proconflict effects of corticotropin, a benzodiazepine inverse agonist and electric foot shock. J. Pharmacol. Exp. Ther. 1992 / 262 (1) / 335-342. , Little, H.J. et al, The benzodiazepines : anxiolytic and withdrawal effects. Neuropeptides 1991 / 19 / suppl. 11-14. , Eisenberg, R.M. et al, Effects of beta-carboline-ethyl ester on plasma corticosterone -- a parallel with antagonist-precipated diazepam withdrawal. Life Sci. 1989 / 44 (20) / 1457-1466. , Maiewski, S.F. et al, Evidence that a benzodiazepine receptor mechanism regulates the secretion of pituitary beta-endorphin in rats. Endocrinology 1985 / 117 (2) / 474-480.

(2) (no author listed) Tetrahydro-beta-carbolines in foodstuffs, urine, and milk : physiological implications. Nutr. Rev. 1991 / 49 (12) / 367-368.

(3) Papavergou, E. et al, Tetrahydro-beta-carboline-carboxylic acids in smoked foods. Food Addit. Contam. 1992 / 9 (1) / 83-95.

(4) Simat, T. et al, Unerw├╝nschte Nebenprodukte in biotechnologisch hergestelltern L-tryptophan. GIT Fachzeitschrift f├╝r das Laboratorium 1996 / H.4 /339-344.

(5) Rommelspacher, H. et al, Is there a correlation between the concentration of beta-carbolines and their pharmacolodynamic effects ? Prog. Clin. Biol. Res. 1982 / 90 / 41-55.

(6) Airaksinen, M.M. et al, Affinity of beta-carboline on rat brain benzodiazepine and opiate binding sites. Med. Biol. 1980 / 58 (6) / 341-344.

(7) Wakabayashi, K. et al, Recently identified nitrite-reactive compounds in food : occurence and biological properties of the nitrosated products. IARC Sci. Publ. 1987 / 84 / 287-291.

(8) Jolivette, L.J. et al, Thietanium ion formation from the food mutagen 2-chloro-4-(methylthio)butanoic acid. Chem. Res. Toxicol. 1998 / 11 (7) / 794-799.

(9) Sugimura, T. et al, Carcinogenic, Mutagenic, and Comutagenic Aromatic Amines in Human Foods. Natl. Cancer Inst. Monogr. 1981 / 58 / 27-33.

(10) Overvik, E. et al, Influence of creatine, amino acids and water on the formation of the mutagenic heterocyclic amines found in cooked meat. Carcinogenesis 1989 / 10 (12) / 1293-1301. , Yoshida, D. et al, Formation of mutagens by heating foods and model systems. Environ. Health. Perspect. 1986 / 67 / 55-58.

(11) Solyakov, A. et al, Heterocyclic amines in process flavours, process flavour ingredients, bouillon concentrates and a pan residue. Food Chem. Toxicol. 1999 / 37 (1) / 1-11. , Skog, K. et al, Analysis of nonpolar heterocyclic amines in cooked foods and meat extracts using gas chromatography-mass spectometry. J. Chromatogr. A. 1998 / 803 (1-2) / 227-233. , Stavric, B. et al, Mutagenic heterocyclic aromatic amines (HAA's) in 'processed food flavour' samples. Food Chem. Toxicol. 1997 / 35 (2) / 185-197. , Wakabayashi, K. et al, Human exposure to mutagenic / carcinogenic heterocyclic amines and comutagenic beta-carbolines. Mutat. Res. 1997 / 376 (1-2) / 253-259. , Galceran, M.T. et al, Determination of heterocyclic amines by pneumatically assisted electrospray liquid chromatography-mass spectometry. J. Chromatogr. A. 1996 / 730 (1-2) / 185-194. , Gross, G.A. et al, Heterocyclic aromatic amine formation in grilled bacon, beef and fish and in grilled scrapings. Carcinogenesis 1993 / 14 (11) / 2313-2318. , Sugimura, T. et al, Mutagenic factors in cooked foods. Crit. Rev. Toxicol. 1979 / 6 (3) / 189-209.

(12) Rommelspacher, H. et al, beta-Carbolines and tetrahydroisoquinolines : detection and function in mammals. Planta. Med. 1991 / 57 (7) / 585-592. , Pawlik, M. et al, Quantitative autoradiograph of (3H)norharman ((3H)beta-carboline) binding sites in the rat brain. J. Chem. Neuroanal. 1990 / 3 (1) / 19-24. , Rommelspacher, H. et al, Harman induces preference for ethanol in rats : is the effect specific for ethanol ? Parhmacol. Biochem. Behav. 1987 / 26 (4) / 749-755. , Rommelspacher, H. et al, Benzodiazepine antagonism by harmane and other beta-carbolines in vitro and in vivo. Eur. J. Pharmacol. 1981 / 70 (3) / 409-416.

(13) Totsuka, Y. et al, Structural determination of a mutagenic aminophenylnorharman produced by the co-mutagen norharman with aniline. Carcinogenesis 1998 / 19 (11) / 1995-2000. , Skog, K. et al, Analysis of nonpolar heterocyclic amines in cooked foods and meat extracts using gas chromatography-mass spectometry. J. Chromatogr. A. 1998 / 803 (1-2) / 227-233.

(14) Vikse, R. et al, Heterocyclic amines in cooked meat. (in Norwegian) Tidsskr. Nor. Laegeforen. 1999 / 119 (1) / 45-49. , Sinha, R. et al, Heterocyclic amine content of pork products cooked by different methods and to varying degrees of doneness. Food Chem. Toxicol. 1998 / 36 (4) / 289-297. , Byrne ,C. et al, Predictors of heterocyclic amines intake in three prospective cohorts. Cancer Epidemiol. Biomarkers 1998 / 7 (6) / 523-529. , Kaplan, S. et al, Nutritional factors in the etiology of brain tumors : potential role of nitrosamines, fat, and cholesterol. Am. J. Epidemiol. 1997 / 146 (10) / 832-841. , Ward, M.H. et al, Risk of adenocarcinoma of the stomach and esophagus with meat cooking method and doneness preference. Int. J. Cancer 1997 / 71 (1) / 14-19. , La Vecchia, C. et al, Selected micronutrient intake and the risk of gastric cancer. Cancer Epidemiol. Biomarkers Prev. 1994 / 3 (5) / 393-398. , Buiatti, E. et al, A case-control study of gastric cancer and diet in Italy : II. Association with nutrients. Int. J. Cancer 1990 / 45 (5) / 896-901. , Proliac, A. et al, Isolation and identification of two beta-carbolins in roasted chicory root. Helv. Chim. Acta 1976 / 59 (7) / 2503-2507. (in french)

(15) Salmon, C.P. et al, Effects of marinating on heterocyclic amine carcinogen formation in grilled chicken. Food Chem. Toxicol. 1997 / 35 (5) / 433-441. , Shibata, A. et al, Dietary beta-carotene, sigarette smoking and lung cancer in men. Cancer Causes Control 1992 / 3 (3) / 207-214.

(16) Chiu, C.P. et al, Formation of heterocyclic amines in cooked chicken legs. J. Food Prot. 1998 / 61 (6) / 712-719. , Byrne, C. et al, Predictors of dietary heterocyclic amine intake in three prospective cohorts. Cancer Epidemiol. Biomarkers Prev. 1998 / 7 (6) / 523-529. , Wakabayashi, K. et al, Human exposure to mutagenic / carcinogenic heterocyclic amines and co-mutagenic beta-carbolines. Mutat. Res. 1997 / 376 (1-2) / 253-259. , Salmon, C.P. et al, Effects of marinating on heterocyclic amine carcinogen formation in grilled chicken. Food Chem Toxicol. 1997 / 35 (5) / 433-441. , Skog, K. et al, Polar and non-polar heterocyclic amines in cooked fish and meat products and their corresponding pan residues. Food Chem. Toxicol. 1997 / 35 (6) / 555-565. , Pfau, W. et al, Characterization of the major DNA adduct formed by the food mutagen 2-amino-3-methyl-9H-pyrido(2,3-b)indole (MeAalphaC) in primary rat hepatocytes. Carcinogenesis 1996 / 17 (12) / 2727-2732. , Thiebaud, H.P. et al, Airborne mutagens produced by frying beef, pork and soy-based food. Food and Chemical Toxicology 1995 / 10 / 821-828. , Ohgaki, H. et al, Carcinogenicity in mice of mutagenic compounds from glutamic acid and soybean globulin pyrolysates. Carcinogenesis. 1984 / 5 (6) / 815-819. , Tomita, I. et al, Mutagenicity of various Japanese foodstuffs treated with nitrite. II. Directly acting mutagens produced from N-containing compounds in foodstuffs. IARC Sci. Publ. 1984 / 57 / 33-41.

(17) Knize, M.G. et al, Characterization of mutagenic activity in cooked-grain-food products. Food Chem. Toxicol. 1994 / 32 (1) / 15-21.

(18) Ozawa, Y. et al, Occurence of stereoisomers of 1-(2'-pyrrolidinethione-3'-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid in fermented radish roots and their different mutagenic properties. Biosci. Biotechnol. Biochem. 1999 / 63 (1) / 216-219. , Sen, N.P. et al, Analytical methods for the determination and mass spectometric confirmation of 1-methyl-2-nitroso-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid and 2-nitroso-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid in foods. Food. Addit. Contam. 1991 / 8 (3) / 275-289. , Sugimura, T. et al, Mutagenic factors in cooked foods. Crit. Rev. Toxicol. 1979 / 6 (3) / 189-209.

(19) Herraiz, T. et al, Presence of tetrahydro-beta-carboline-3-carboxylic acids in foods by gas chromatography-mass spectometry as their N-methoxycarbonylmethyl ester derivates. J. Chromatogr. A. 1997 / 765 (2) / 265-277.

(20) Skog, K.I. et al, Carcinogenic heterocyclic amines in model systems and cooked foods : a revieuw on formation, occurence and intake. Food Chem. Toxicol. 1998 / 36 (9-10) / 879-896.

(21) Kurosaka, R. et al, Detection of 2-amino-1-methyl-6-(4-hydroxyphenyl)imidazo(4,5-b) pyridine (4'-OH-PhIP) level comparable to PhIP. Jpn. J. Cancer Res. 1992 / 83 (9) / 919-922.

(22) Okogoni, H. et al, Induction of aberrent cryptfoci in C57BL/6N mice by 2-amino-9H-pyrido(2,3-b)indole (AalphaC) and 2-amino-3,8-dimethylimidazo(4,5-f)quinoxaline (MeIQx) Cancer Lett. 1997 / 111 (1-2) / 105-109. , Zhang, X.B. et al, Intestinal mutagenicity of two carcinogenic food mutagens in transgenic mice : 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine and amino(alpha)carboline. Carcinogenesis 1996 / 17 (10) / 2259-2265. , Yoo, M.A. et al, Mutagenic potency of heterocyclic amines in the Drosophila wing spot test and its correlation to carcinogenic potency. Jpn. J. Cancer Res. 1985 / 76 (6) / 468-473.

(23) Beamand, J.A. et al, Effect of some cooked food mutagens on unscheduled DNA synthesis in cultured precision-cut rat, mouse and human liver slices. Food Chem. Toxicol. 1998 / 36 (6) / 455-466. , Yoshida, D. et al, Formation of mutagens by heating foods and model systems. Environ. Health Perspect. 1986 / 67 / 55-58. , Ohgaki, H. et al, Carcinogenicity in mice of mutagenic compounds from glutamic acid and soybean globulin pyrolysates. Carcinogenesis. 1984 / 5 (6) / 815-819.

(24) Pfau, W. et al, Characterization of the major DNA adduct formed by the food mutagen 2-amino-3-methyl-9H-pyrido(2,3-b)indole (MeAalphaC) in primary rat hepatocytes. Carcinogenesis 1996 / 17 (12) / 2727-2732. , Pfau, W. et al, Pancreatic DNA adducts formed in vitro and in vivo by the food mutagens 2-amino-1-methyl-6-phenylimidazo(4,5-b)prydine (PhIP) and 2-amino-3-methyl-9H-pyrido(2,3-b)indole (MeAalphaC). Mutat. Res. 1997 / 378 (1-2) / 13-22.

(25) Skog, K. et al, Analysis of nonpolar heterocyclic amines in cooked foods and meat extracts using gas chromatography-mass spectometry. J. Chromatogr. A. 1998 / 803 (1-2) / 227-233. , Galceran, M.T. et al, Determination of heterocyclic amines by pneumatically assisted electrospray liquid chromatography-mass spectometry. J. Chromatogr. A. 1996 / 730 (1-2) / 185-194. , Yamaguchi, K. et al, Presence of 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole in broiled beef. Gann. 1980 / 71 (5) / 745-746. , Yamaizumi, Z. et al, Detection of potent mutagens, Trp-P-1 and Trp-P-2 in broiled fish. Cancer Lett. 1980 / 9 (2) / 75-83. , Sugimura, T. et al, Mutagenic factors in cooked foods. Crit. Rev. Toxicol. 1979 / 6 (3) / 189-209.

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