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Heterocyclic amines

Heterocyclic amines

Overview
Heterocyclic amines, also sometime referred to as HCAs, contain both heterocyclic and amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...

 groups. While some heterocycles are amines themselves, the amines indicated in the name are those attached to the heterocyclic ring.

Some heterocyclic amines (HCAs) found in cooked meat are known carcinogen
Carcinogen
A carcinogen is any substance, radionuclide or radiation that is an agent directly involved in the promotion of cancer or in the increase of its propagation. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...

s. Research has shown that cooking certain meats at high temperatures creates chemicals that are not present in uncooked meats.
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Encyclopedia
Heterocyclic amines, also sometime referred to as HCAs, contain both heterocyclic and amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...

 groups. While some heterocycles are amines themselves, the amines indicated in the name are those attached to the heterocyclic ring.

Heterocyclic amines and cancer


Some heterocyclic amines (HCAs) found in cooked meat are known carcinogen
Carcinogen
A carcinogen is any substance, radionuclide or radiation that is an agent directly involved in the promotion of cancer or in the increase of its propagation. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...

s. Research has shown that cooking certain meats at high temperatures creates chemicals that are not present in uncooked meats. For example, heterocyclic amines are the carcinogenic chemicals formed from the cooking of muscle meats such as beef
Beef
Beef is the culinary name for meat from bovines, especially domestic cattle . Beef is one of the principal meats used in the cuisine of Australia, Europe and America, and is also important in Africa, East Asia, and Southeast Asia...

, pork
Pork
Pork is the culinary name for meat from the domestic pig . The word pork often denotes specifically the fresh meat of the pig, but can be used as an all-inclusive term which includes cured, smoked, or processed meats It is one of the most-commonly consumed meats worldwide, with evidence of pig...

, fowl
Fowl
Fowl is a word for birds in general but usually refers to birds belonging to one of two biological orders, namely the gamefowl or landfowl and the waterfowl...

, and fish
Fish
A fish is any aquatic vertebrate animal that is typically ectothermic , covered with scales, and equipped with two sets of paired fins and several unpaired fins...

. HCAs form when amino acids and creatine
Creatine
Creatine is a nitrogenous organic acid that occurs naturally in vertebrates and helps to supply energy to muscle. Creatine was identified in 1832 when Michel Eugène Chevreul discovered it as a component of skeletal muscle, which he later named creatine after the Greek word for flesh,...

 (a chemical found in muscles) react at high cooking temperatures. Researchers have identified 17 different HCAs resulting from the cooking of muscle meats that may pose human cancer risk. NCI's Division of Cancer Epidemiology and Genetics found a link between individuals with stomach cancer
Stomach cancer
Stomach or gastric cancer can develop in any part of the stomach and may spread throughout the stomach and to other organs; particularly the esophagus, lungs and the liver. Stomach cancer causes about 800,000 deaths worldwide per year.-Epidemiology:...

 and the consumption of cooked meat, and other studies for colorectal, pancreatic, and breast cancer
Breast cancer
Breast cancer is a cancer that starts in the breast, usually in the inner lining of the milk ducts or lobules. There are different types of breast cancer, with different stages , aggressiveness, and genetic makeup. With best treatment, 10-year disease-free survival varies from 98% to 10%...

 is associated with high intakes of well-done, fried, or barbecue
Barbecue
Barbecue or barbeque is a method and apparatus for cooking meat, with the heat and hot gases of a fire, smoking wood, or hot coals of charcoal or a propane gas grill, and may...

d meats. People who eat medium-well or well done beef were more than three times as likely to suffer stomach cancer as those who ate rare or medium-rare beef. Other sources of protein
Protein
Proteins are organic compounds made of amino acids arranged in a linear chain and folded into a globular form. The amino acids in a polymer chain are joined together by the peptide bonds between the carboxyl and amino groups of adjacent amino acid residues...

 (milk
Milk
Milk is an opaque white liquid produced by the mammary glands of mammals. It provides the primary source of nutrition for young mammals before they are able to digest other types of food. The early lactation milk is known as colostrum, and carries the mother's antibodies to the baby. It can reduce...

, eggs
Egg (food)
An egg is a round or oval body laid by the female of any number of different species, consisting of an ovum surrounded by layers of membranes and an outer casing, which acts to nourish and protect a developing embryo and its nutrient reserves...

, tofu
Tofu
or called toufu, bean curd is a soft white food made by coagulating soy milk, and then pressing the resulting curds into blocks. It is of Chinese origin, and part of East Asian and Southeast Asian cuisine such as Chinese, Japanese, Korean, Vietnamese and others. There are many different varieties...

, and organ meats such as liver
Liver
The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...

) have very little or no HCA content naturally or when cooked.

Research has shown that an olive oil, lemon juice and garlic marinade cut HCA levels in chicken by as much as 90%. 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. However, researchers say that "It may seem appetising to marinate steak in beer or wine, but this will have a minimal impact on the effect of the meat on your cancer risk and the best way to reduce your risk of cancer from eating red and processed meat is to eat less of it overall".