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Encyclopedia > Norepinephrine
Norepinephrine[1]
Chemical structure of norepinephrine
Chemical name 4-(2-Amino-1-hydroxyethyl)
benzene-1,2-diol
Other names Noradrenaline
Chemical formula C8H11NO3
Molecular mass 169.18 g/mol
CAS number D: [149-95-1]
L: [51-41-2]
D/L: [138-65-8]
Melting point L: 216.5-218 °C (decomp.)
D/L: 191 °C (decomp.)
SMILES NC[C@H](O)c1ccc(O)c(O)c1
Disclaimer and references

Norepinephrine (INN)(abbr. norepi) or noradrenaline (BAN) is a catecholamine and a phenethylamine with chemical formula C8H11NO3. The natural stereoisomer is L-(−)-(R)-norepinephrine. The prefix nor- stands for the German abbreviation "Nitrogenium Ohne Rest" meaning "Nitrogen without rest" referring to the absence of a methyl group at the N-atom present in epinephrine/adrenaline. It is released from the medulla of the adrenal glands as a hormone into the blood, but it is also a neurotransmitter in the central nervous system and sympathetic nervous system where it is released from noradrenergic neurons during synaptic transmission. As a stress hormone, it affects parts of the human brain where attention and responding actions are controlled. Along with epinephrine, norepinephrine underlies the fight-or-flight response, directly increasing heart rate, triggering the release of glucose from energy stores, and increasing skeletal muscle readiness. Image File history File links Size of this preview: 800 × 549 pixelsFull resolution (1111 × 762 pixel, file size: 3 KB, MIME type: image/png) High-resolution black/white . ... Image File history File links Size of this preview: 709 × 600 pixelsFull resolution (758 × 641 pixel, file size: 96 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Norepinephrine User:Sbrools/Gallery ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... A British Approved Name (BAN) is the official non-proprietary or generic name given to a pharmaceutical substance, as defined in the British Pharmacopoeia (BP). ... tyrosine is the precursor of catecholamines epinephrine norepinephrine dopamine Synthesis Catecholamines are chemical compounds derived from the amino acid tyrosine containing catechol and amine groups. ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... Stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in space is different in each isomer. ... nor- is a chemical acronym and prefix. ... Medulla in general means the inner part, and derives from the Latin word for marrow. In medicine it is contrasted to the cortex. ... In mammals, the adrenal glands (also known as suprarenal glands) are the triangle-shaped endocrine glands that sit on top of the kidneys; their name indicates that position (ad-, near or at + -renes, kidneys). They are chiefly responsible for regulating the stress response through the synthesis of corticosteroids and catecholamines... Norepinephrine A hormone (from Greek όρμή - to set in motion) is a chemical messenger from one cell (or group of cells) to another. ... Chemical structure of D-aspartic acid, a common amino acid neurotransmitter. ... A diagram showing the CNS: 1. ... Grays FIG. 838– The right sympathetic chain and its connections with the thoracic, abdominal, and pelvic plexuses. ... Neurons (also called nerve cells) are the primary cells of the nervous system. ... Synapses allow nerve cells to communicate with one another through axons and dendrites, converting electrical signals into chemical ones. ... Stress hormones such as cortisol and norepinephrine are released at periods of high stress. ... The human brain is the most complex organ in the human body. ... It has been suggested that Neural mechanisms behind shifts of attention be merged into this article or section. ... Adrenaline redirects here. ... The fight-or-flight response, also called the acute stress response, was first described by Walter Cannon in 1929. ... Heart rate is a term used to describe the frequency of the cardiac cycle. ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ... This article or section does not cite any references or sources. ...


However, when norepinepherine acts as a drug, it will increase systolic and diastolic pressure, causing compensatory vagal reflex, which overcomes its direct cardioaccelerator action. Therefore, it will cause reflex bradycardia in patient. Systolic is the adjective form of systole, typically referring to the contraction activity of the heart. ... Diastolic is the adjective form of diastole referring to relaxation of the heart, between muscle contractions. ... Bradycardia, as applied in adult medicine, is defined as a heart rate of under 60 beats per minute, though it is seldom symptomatic until the rate drops below 50 beat/min [1]. It is also less commonly known as brachycardia. ...


Norepinephrine is released when a host of physiological changes are activated by a stressful event. This is caused in part by activation of an area of the brain stem called the locus ceruleus. This nucleus is the origin of most norepinephrine pathways in the brain. Neurons that are activated by norepinephrine project bilaterally (send signals to both sides of the brain) from the locus ceruleus along distinct pathways to many locations, including the cerebral cortex, limbic system, and the spinal cord. The locus ceruleus (or "LC") is located within the dorsal wall of the rostral pons in the lateral floor of the fourth ventricle (see picture). This article or section does not cite any references or sources. ... Mostly enveloped by the cerebrum and cerebellum (blue), the visible part of brainstem is shown in black. ... The Locus ceruleus, also spelled locus caeruleus or locus coeruleus (Latin for the blue spot), is a nucleus in the brain stem responsible for physiological responses to stress and panic. ... Location of the cerebral cortex Slice of the cerebral cortex, ca. ... The limbic system (Latin limbus: border or edge) includes the structures in the human brain involved in emotion, motivation, and emotional association with memory. ... The Spinal cord nested in the vertebral column. ...


At synapses, norepinephrine acts on both alpha and beta adrenoreceptors.


The adrenergic receptors (or adrenoceptors) are a class of G_protein coupled receptors that is the target of catecholamines. ...

Brain: Pons
Latin pons

Contents

Image File history File links Gray768. ... Latin is an ancient Indo-European language originally spoken in Latium, the region immediately surrounding Rome. ...

Natural Production

Norepinephrine is naturally released both in the central nervous system where it helps control alertness and arousal, and from peripheral sympathetic nerves where it exerts diverse effects on its target organs. Arousal is a physiological and psychological state of being awake. ...


Clinical uses

Attention-deficit/hyperactivity disorder

Norepinephrine, along with dopamine, has come to be recognized as playing a large role in attention and focus. For people with ADD/ADHD, psychostimulant medications such as Ritalin/Concerta (methylphenidate), Dexedrine (dextroamphetamine), and Adderall (a mixture of dextroamphetamine and racemic amphetamine salts) are prescribed to help increase levels of norepinephrine and dopamine. Strattera (atomoxetine) is a selective norepinephrine reuptake inhibitor, and is a unique ADD/ADHD medication, as it affects only norepinephrine, rather than dopamine. As a result, Strattera has a lower abuse potential. However, it may not be as effective as the psychostimulants are with many people who have ADD/ADHD. Consulting with a physician or Nurse practitioner is needed to find the appropriate medication and dosage. (Other SNRIs, currently approved as antidepressants, have also been used off-label for treatment of ADD/ADHD.) Dopamine is a phenethylamine naturally produced by the human body. ... PET scans measure the activity of various parts of the brain at a particular time The image on the left illustrates areas of activity in the brain of a person without ADHD while doing an assigned task. ... Vitamin R redirects here. ... Dextroamphetamine is a powerful psychostimulant which produces increased wakefulness, energy and self-confidence in association with decreased fatigue and appetite. ... Adderall 25 mg XR Capsules Adderall is a pharmaceutical stimulant amphetamine used to treat attention-deficit disorder/attention-deficit hyperactivity disorder and narcolepsy. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecule. ... Amphetamine or Amfetamine (Alpha-Methyl-PHenEThylAMINE), also known as, beta-phenyl-isopropylamine, and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ... Atomoxetine is the first non-stimulant drug approved for the treatment of attention-deficit hyperactivity disorder (ADHD). ... A selective norepinephrine reuptake inhibitor or SNRI is a drug that inhibits the reuptake of norepinephrine by neurons, so that more of this neurotransmitter remains in the synapse. ... // A nurse practitioner (NP) is a registered nurse who has completed advanced education (generally a minimum of a masters degree) and training in the diagnosis and management of common medical conditions, including chronic illnesses. ... The term off-label refers to the use of a drug for a medical condition other than for which it was officially approved and marketed. ...


Depression

Differences in the norepinephrine system are implicated in depression. Serotonin-norepinephrine reuptake inhibitors (SNRIs) are antidepressants that treat depression by increasing the amount of serotonin and norepinephrine available to postsynaptic cells in the brain. There is some recent evidence showing that the norepinephrine transporter also transports some dopamine as well, implying that SNRIs may also increase dopamine transmission[citation needed]. This is because SNRIs work by inhibiting reuptake, i.e. preventing the serotonin and norepinephrine transporters from taking their respective neurotransmitters back to their storage vesicles for later use. If the norepinephrine transporter normally recycles some dopamine too, then SNRIs will also enhance dopaminergic transmission. Therefore, the antidepressant effects associated with increasing norepinephrine levels may also be partly or largely due to the concurrent increase in dopamine (particularly in the prefrontal cortex). Clinical depression (also called major depressive disorder, or unipolar depression when compared to bipolar disorder) is a state of intense sadness, melancholia or despair that has advanced to the point of being disruptive to an individuals social functioning and/or activities of daily living. ... Serotonin Norepinephrine Serotonin-norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant used in the treatment of clinical depression and other affective disorders. ... An antidepressant is a medication used primarily in the treatment of clinical depression. ... Serotonin (pronounced ) (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract of animals including humans. ... A synapse is a connection between two neurons: presynaptic and postsynaptic. ... The norepinephrine transporter or NET is a monoamine transporter that transports the neurotransmitter norepinephrine from the synapse back to its vesicles for storage until later use. ... Dopamine is a phenethylamine naturally produced by the human body. ... Serotonin norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant used in the treatment of clinical depression and other affective disorders. ... Dopamine is a phenethylamine naturally produced by the human body. ... Serotonin norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant used in the treatment of clinical depression and other affective disorders. ... Serotonin (pronounced ) (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract of animals including humans. ... Chemical structure of D-aspartic acid, a common amino acid neurotransmitter. ... The norepinephrine transporter or NET is a monoamine transporter that transports the neurotransmitter norepinephrine from the synapse back to its vesicles for storage until later use. ... Dopamine is a phenethylamine naturally produced by the human body. ... Serotonin norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant used in the treatment of clinical depression and other affective disorders. ... Dopamine is a chemical naturally produced in the body. ... A recent form of antidepressant medication - Prozac Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant, in the most common usage, is a psychiatric medication taken to alleviate clinical depression or dysthymia (milder depression). ... Dopamine is a phenethylamine naturally produced by the human body. ... The prefrontal cortex is the anterior part of the frontal lobes of the brain, lying in front of the motor and premotor areas. ...


Tricyclic antidepressants (TCAs) increase norepinephrine activity as well. Most of them also increase serotonin activity, but tend to have side effects due nonspecific activation of histamine and acetylcholine receptors. Side effects include tiredness, increased hunger, dry mouth, and blurred vision. For this reason, they have largely been replaced by newer selective reuptake drugs such as Prozac. Chemical structure of the tricyclic antidepressant amitriptyline. ... Serotonin (pronounced ) (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract of animals including humans. ... This article or section does not cite any references or sources. ... The chemical compound acetylcholine, often abbreviated as ACh, was the first neurotransmitter to be identified. ... Background Fluoxetine hydrochloride (brand names include Prozac®, Symbyax® (compounded with olanzapine), Sarafem®, Fontex® (Sweden), Fluctine (Austria, Germany), Prodep (India), Fludac (India)) is an antidepressant drug used medically in the treatment of depression, obsessive-compulsive disorder, bulimia nervosa, premenstrual dysphoric disorder, and many other disorders. ...


Vasoconstriction

Norepinephrine is also used as a vasopressor medication (for example, brand name Levophed) for patients with critical hypotension. It is given intravenously and acts on both alpha-1 and alpha-2 adrenergic receptors to cause vasoconstriction. Its effect in vitro is often limited to the increasing of blood pressure through agonistic activity on alpha-1 and alpha-2 receptors and causing a resultant increase in peripheral vascular resistance. In high dose and especially when it is combined with other vasopressors, it can lead to limb ischemia and limb death. Norepinephrine is mainly used to treat patients in vasodilatory shock states such as septic shock and neurogenic shock and has shown a survival benefit over dopamine. Vasopressor is a drug used to constrict the arteries and increase blood pressure. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... Total peripheral resistance refers the cumulative resistance of the thousands of arterioles in the body, or the lungs, respectively. ... In medicine, ischemia (Greek ισχαιμία, isch- is restriction, hema or haema is blood) is a restriction in blood supply, generally due to factors in the blood vessels, with resultant damage or dysfunction of tissue. ... Septic shock is a serious medical condition causing such effects as multiple organ failure and death in response to infection and sepsis. ... Neurogenic shock is shock caused by hiv aids the sudden loss of the sympathetic nervous system signals to the smooth muscle in vessel walls. ... Dopamine is a phenethylamine naturally produced by the human body. ...


Biosynthesis

Norepinephrine is synthesized by a series of enzymatic steps in the adrenal medulla from the amino acid tyrosine: In mammals, the adrenal glands are the triangle-shaped endocrine glands that sit atop the kidneys. ... Phenylalanine is one of the standard amino acids. ... Tyrosine (from the Greek tyros, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in cheese[1][2]), 4-hydroxyphenylalanine, or 2-amino-3(4-hydroxyphenyl)-propanoic acid, is one of the 20 amino acids that are used by cells to synthesize proteins. ...

Metabolites

In mammals, norepinephrine is rapidly degraded to various metabolites. The principal metabolites are: A metabolite is the product of metabolism. ...

  • Normetanephrine (via the enzyme catechol-O-methyl transferase, COMT)
  • 3,4-Dihydroxymandelic acid (via monoamine oxidase, MAO)
  • 3-Methoxy-4-hydroxymandelic acid (via MAO)
  • 3-Methoxy-4-hydroxyphenylglycol (via MAO)
  • Epinephrine (via PNMT[2])

Normetanephrine is a metabolite of norepinephrine. ... Catechol-O-methyl transferase (COMT) (EC 2. ... MAO-A is an abbreviation for monoamine oxidase A. There are 2 varieties of monoamine oxidase, which are MAO-A and MAO-B. MAO-A mainly breaks down the neurochemicals serotonin and norepinephrine, whereas MAO-B mainly breaks down the neurochemicals dopamine and phenylethylamine. ... MAO-A is an abbreviation for monoamine oxidase A. There are 2 varieties of monoamine oxidase, which are MAO-A and MAO-B. MAO-A mainly breaks down the neurochemicals serotonin and norepinephrine, whereas MAO-B mainly breaks down the neurochemicals dopamine and phenylethylamine. ... MAO-A is an abbreviation for monoamine oxidase A. There are 2 varieties of monoamine oxidase, which are MAO-A and MAO-B. MAO-A mainly breaks down the neurochemicals serotonin and norepinephrine, whereas MAO-B mainly breaks down the neurochemicals dopamine and phenylethylamine. ... Adrenaline redirects here. ... Phenylethanolamine N-methyltransferase (PNMT) is an enzyme found in the adrenal medulla which converts Norepinephrine (Noradrenalin) to Epinephrine (Adrenalin). ...

References

Brunton, Lazo, Parker: Goodmn &Gilman's The Pharmacological Basis of Therapeutics. McGraw Hill, 11th edition. p248~249

  1. ^ Merck Index, 11th Edition, 6612.
  2. ^ "Endokrynologia Kliniczna" ISBN 83-200-0815-8, page 502

External links


  Results from FactBites:
 
Olympus MIC-D: Polarized Light Gallery - Norepinephrine (304 words)
Norepinephrine is released at the synapses (in a manner similar to other neurotransmitters), transmitting neural signals from a nerve to other cells in the body.
Norepinephrine also triggers increases in the conversion of glycogen to glucose in the liver (glycogenolysis), assists in the conversion of fats to fatty acids in the adipose tissue (lipolysis), and is responsible for relaxation of the bronchial smooth muscles, opening the air passages to the lungs.
To biochemists, norepinephrine is also known as leva-arterenol, and it differs from epinephrine by the absence of a methyl group on the nitrogen atom.
Norepinephrine - Wikipedia, the free encyclopedia (746 words)
Therefore, the antidepressant effects associated with increasing norepinephrine levels may also be partly or largely due to the concurrent increase in dopamine (particularly in the prefrontal cortex).
Norepinephrine (commonly referred to by the brand name Levophed) is also a powerful medicine used in critically-ill patients as a vasopressor.
Norepinephrine is mainly used to treat patients in septic shock and has shown a survival benefit over dopamine.
  More results at FactBites »

 
 

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