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- Molecular formula: C8H11NO2
- Molar mass: 153.178
- CAS Registry Number: 51-61-6
- Appearance: Not available
- Melting point: 128
- Boiling point: Not available
- Solubility: Not available
- Safety sheet: Not available
- Spectra: Massbank MS (1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76), also check on SDBS. Add Spectra (Help).
Dopamine (contracted from 3,4-dihydroxyphenethylamine) is a neurotransmitter of the catecholamine and phenethylamine families that plays a number of important roles in the human brain and body. Its name derives from its chemical structure: it is an amine that is formed by removing a carboxyl group from a molecule of L-DOPA.
In the brain, dopamine functions as a neurotransmitter—a chemical released by nerve cells to send signals to other nerve cells. The brain includes several distinct dopamine systems, one of which plays a major role in reward-motivated behavior. Most types of reward increase the level of dopamine in the brain, and a variety of addictive drugs increase dopamine neuronal activity. Other brain dopamine systems are involved in motor control and in controlling the release of several other important hormones.
Several important diseases of the nervous system are associated with dysfunctions of the dopamine system. Parkinson's disease, a degenerative condition causing tremor and motor impairment, has been related to the loss of dopamine-secreting neurons in the midbrain area called the substantia nigra. There is evidence that schizophrenia involves highly altered levels of dopamine activity, and the antipsychotic drugs that are frequently used to treat it have a primary effect of attenuating dopamine activity. Attention deficit hyperactivity disorder (ADHD) and restless legs syndrome (RLS) are also believed to be associated with decreased dopamine activity.
Outside the nervous system, dopamine functions in several parts of the body as a local chemical messenger. In the blood vessels, it inhibits norepinephrine release and acts as a vasodilator; in the kidneys, it increases sodium excretion and urine output; in the pancreas, it reduces insulin production; in the digestive system, it reduces gastrointestinal motility and protects intestinal mucosa; and in the immune system, it reduces the activity of lymphocytes. With the exception of the blood vessels, dopamine in each of these peripheral systems has a "paracrine" function: it is synthesized locally and exerts its effects on cells that are located near the cells that release it.
A variety of important drugs work by altering the way the body makes or uses dopamine. Dopamine itself is available for intravenous injection: although it cannot reach the brain from the bloodstream, its peripheral effects make it useful in the treatment of heart failure or shock, especially in newborn babies. L-DOPA, the metabolic precursor of dopamine, does reach the brain and is the most widely used treatment for Parkinson's disease. Dopaminergic stimulants can be addictive in high doses, but some are used at lower doses to treat ADHD. Conversely, many antipsychotic drugs act by suppressing the effects of dopamine. Drugs that act against dopamine by a different mechanism are also some of the most effective anti-nausea agents.
Preparations containing dopamine hydrochloride are used in the treatment of acute heart failure, kidney failure, myocardial infarction, septic shock, etc. and are on the World Health Organization's List of Essential Medicines (WHO-EM), a list of medicines that are essential for a basic health system.
4-(2-Aminoethyl)-1,2-benzenediol (IUPAC Name); 4-(2-Aminoethyl)-1,2-benzoldiol; 4-(2-aminoethyl)benzene-1,2-diol; 4-(2-aminoethyl)-pyrocatechol; alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane; DA; Dophamine
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