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than in controls, there is no direct correlation between blood-levels and levels of daily meat consumption, suggesting a difference in metabolism of this chemical plays a greater role. These chemicals are formed during the cooking process of meat, particularly the longer they are cooked, and the more
101:
is another compound made up of molecules with a five-membered heterocyclic ring. These molecules are unsaturated and contain a nitrogen atom in the ring. Four pyrrole rings are joined in a ring structure called a
603:
Melo A, Viegas O, Petisca C, Pinho O, Ferreira IM (November 2008). "Effect of beer/red wine marinades on the formation of heterocyclic aromatic amines in pan-fried beef".
212:
265:, a β-carboline alkaloid found in meats is "highly tremorogenic" (tremor inducing). While harmane has been found in roughly 50% higher concentrations in patients with
342:
93:
is a molecule containing a pyrrolidine ring attached to a ring of pyridine (other heterocyclic amine). Nicotine belongs to a group of compounds known as
321:
176:
is a heterocyclic amine that contains two nitrogen atoms in an unsaturated six-membered ring. An example of a molecule that contains pyrimidine is
89:
is composed of molecules that contain a saturated ring of five atoms. This cyclic structure is composed of one atom of nitrogen and four carbon.
287:
225:
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except that a nitrogen atom replaces one carbon atom. Pyridine is used as a flavoring agent. The pyridine ring is part of two B vitamins:
228:
occurs at high cooking temperatures. Heterocyclic amines are the carcinogenic chemicals formed from the cooking of muscle meats such as
278:
Six hours of marinating in beer or red wine cut levels of two types of HCA in beef steak by up to 90% compared with unmarinated steak.
158:. Niacin, also called nicotinic acid, is found in most organisms. Via metabolism, it becomes nicotinamide adenine dinucleotide NAD, a
695:"Quantification of the neurotoxic beta-carboline harmane in barbecued/grilled meat samples and correlation with level of doneness"
548:"Quantification of the neurotoxic beta-carboline harmane in barbecued/grilled meat samples and correlation with level of doneness"
292:
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49:(nitrogen-containing) group. Typically it is a nitrogen atom of an amine group that also makes the ring heterocyclic (e.g.,
65:. Carcinogenic heterocyclic amines are created by high temperature cooking of meat and smoking of plant matter like
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which is involved in oxidation and reduction in metabolic cells. A deficiency of niacin leads to a disease called
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in hemoglobin, myoglobin, and cytochromes, iron is an ion; in the first two, iron ion is bound to oxygen.
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High-temperature cooking (particularly charring) of meat forms some cancer-causing heterocyclic amines.
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488:"Elevated blood harmane (1-methyl-9H-pyrido[3,4-b]indole) concentrations in essential tremor"
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379:"Toxicokinetics of tremorogenic natural products, harmane and harmine, in male Sprague-Dawley rats"
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ring, which by definition has atoms of at least two different elements, as well as at least one
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Chemicals in Meat Cooked at High
Temperatures and Cancer Risk: NCI (accessed 13 February 2011).
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Some heterocyclic amines (HCAs) found in cooked and especially burned meat are known
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is associated with high intakes of HCAs found in meat cooked at high temperature.
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Louis ED, Zheng W, Applegate L, Shi L, Factor-Litvak P (August 2005).
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57:). The biological functions of heterocyclic amines vary, including
248:(a chemical found in muscles) react at high cooking temperatures.
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180:, which is also known as vitamin B1. Thiamine deficiency produces
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318:"National Cancer Institute – Heterocyclic Amines in Cooked Meats"
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Any heterocyclic compound having at least one nitrogen heteroatom
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Louis ED, Zheng W, Jiang W, Bogen KT, Keating GA (June 2007).
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Louis ED, Zheng W, Jiang W, Bogen KT, Keating GA (June 2007).
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Louis ED, Jiang W, Pellegrino KM, et al. (March 2008).
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cytosine, uracil, and thymine. The other two nucleobases,
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Journal of
Toxicology and Environmental Health, Part A
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Journal of
Toxicology and Environmental Health, Part A
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Journal of
Toxicology and Environmental Health, Part A
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they are exposed to high temperatures during cooking.
26:, essential to many types of life, is an example of a
345:. cancerresearchuk.org. Retrieved 14 December 2022.
343:"Does eating processed and red meat cause cancer?"
41:s, are chemical compounds containing at least one
642:Sugimura T, Nagao M, Wakabayashi K (May 1996).
258:Heterocyclic amines and neurological disorders
200:; they are composed of a fused pyrimidine and
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377:Guan Y, Louis ED, Zheng W (December 2001).
605:Journal of Agricultural and Food Chemistry
69:. Some well known heterocyclic amines are
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77:that encode genetic information in DNA.
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324:from the original on December 21, 2010
196:, are also heterocyclic amines called
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356:"Risk factors for colorectal cancer"
288:Heterocyclic amine formation in meat
226:heterocyclic amine formation in meat
240:, fish and poultry. HCAs form when
184:. Pyrimidine is a component of the
644:"Carcinogenicity of food mutagens"
455:10.1212/01.wnl.0000172352.88359.2d
320:. Cancer.gov. September 15, 2004.
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648:Environmental Health Perspectives
81:Five-membered heterocyclic amines
293:Polycyclic aromatic hydrocarbons
138:Six-membered heterocyclic amines
37:, also sometimes referred to as
208:Heterocyclic amines and cancer
1:
504:10.1016/j.neuro.2007.12.001
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403:10.1080/152873901753246241
224:. Research has shown that
719:10.1080/15287390601172015
572:10.1080/15287390601172015
358:. Canadian Cancer Society
759:Heterocyclic compounds
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146:is similar to that of
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130:. In the centers of
711:2007JTEHA..70.1014L
654:(Suppl 3): 429–33.
564:2007JTEHA..70.1014L
395:2001JTEHA..64..645G
35:Heterocyclic amines
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110:are components of
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28:heterocyclic amine
617:10.1021/jf801837s
252:Colorectal cancer
142:The structure of
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43:heterocyclic
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754:Carcinogens
242:amino acids
222:carcinogens
186:nucleobases
168:amino acids
128:cytochromes
124:chlorophyll
120:vitamin B12
87:pyrrolidine
75:nucleobases
63:carcinogens
748:Categories
299:References
174:Pyrimidine
156:pyridoxine
112:hemoglobin
443:Neurology
274:Marinades
202:imidazole
116:myoglobin
108:porphyrin
104:porphyrin
95:alkaloids
737:17497412
625:18950185
590:17497412
522:18242711
473:16087903
421:11766171
322:Archived
282:See also
246:creatine
182:beriberi
178:thiamine
164:pellagra
160:coenzyme
144:pyridine
91:Nicotine
59:vitamins
55:Zileuton
51:pyridine
728:4993204
707:Bibcode
686:8781358
677:1469643
668:3432798
581:4993204
560:Bibcode
513:2291546
464:4993192
412:4992346
391:Bibcode
362:7 March
263:Harmane
198:purines
194:guanine
190:adenine
148:benzene
99:Pyrrole
67:tobacco
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328:May 1,
152:niacin
126:, and
71:niacin
24:Niacin
664:JSTOR
47:amine
733:PMID
682:PMID
621:PMID
586:PMID
518:PMID
469:PMID
417:PMID
364:2024
330:2010
244:and
238:pork
234:lamb
230:beef
192:and
154:and
132:heme
61:and
723:PMC
715:doi
672:PMC
656:doi
652:104
613:doi
576:PMC
568:doi
508:PMC
500:doi
459:PMC
451:doi
407:PMC
399:doi
39:HCA
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