Heterocyclic amine

Source: Wikipedia, the free encyclopedia.
Niacin
, essential to many types of life, is an example of a heterocyclic amine.

Heterocyclic amines, also sometimes referred to as HCAs, are chemical compounds containing at least one

niacin (vitamin B3), nicotine (psychoactive alkaloid and recreational drug), and the nucleobases
that encode genetic information in DNA.

Five-membered heterocyclic amines

The compound pyrrolidine 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.

alkaloids
, which are naturally occurring organic compounds with nitrogen in them. Pyrrole 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 porphyrin. The rings of
cytochromes. In the centers of heme
in hemoglobin, myoglobin, and cytochromes, iron is an ion; in the first two, iron ion is bound to oxygen.

Six-membered heterocyclic amines

The structure of

niacin and pyridoxine
. Niacin, also called nicotinic acid, is found in most organisms. Via metabolism, it becomes nicotinamide adenine dinucleotide NAD, a
coenzyme which is involved in oxidation and reduction in metabolic cells. A deficiency of niacin leads to a disease called pellagra
. Pyridoxine or vitamin B6, it becomes a major compound in the metabolism of amino acids.

beriberi
. Pyrimidine is a component of the
purines; they are composed of a fused pyrimidine and imidazole
.

Heterocyclic amines and cancer

High-temperature cooking (particularly charring) of meat forms some cancer-causing heterocyclic amines.

Some heterocyclic amines (HCAs) found in cooked and especially burned meat are known

amino acids and creatine (a chemical found in muscles) react at high cooking temperatures.[1]

Colorectal cancer is associated with high intakes of HCAs found in meat cooked at high temperature.[3]

Heterocyclic amines and neurological disorders

Harmane, a β-carboline alkaloid found in meats is "highly tremorogenic" (tremor inducing).[4][5] While harmane has been found in roughly 50% higher concentrations in patients with essential tremor than in controls,[6] 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.[5] These chemicals are formed during the cooking process of meat, particularly the longer they are cooked, and the more they are exposed to high temperatures during cooking.[7][8]

Marinades

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.[9]

See also

References

  1. ^ a b c "National Cancer Institute – Heterocyclic Amines in Cooked Meats". Cancer.gov. September 15, 2004. Archived from the original on December 21, 2010. Retrieved May 1, 2010.
  2. ^ "Does eating processed and red meat cause cancer?". cancerresearchuk.org. Retrieved 14 December 2022.
  3. ^ "Risk factors for colorectal cancer". Canadian Cancer Society. Retrieved 7 March 2024.
  4. PMID 11766171
    .
  5. ^
    PMID 16087903
    .
  6. PMID 18242711
    .
  7. ^ Chemicals in Meat Cooked at High Temperatures and Cancer Risk: NCI (accessed 13 February 2011).
  8. PMID 17497412
    .
  9. PMID 18950185
    .

External links
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