| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:04:45 UTC |
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| Update date | 2019-08-01 18:42:24 UTC |
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| Primary ID | FDB000895 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | (R)-Norepinephrine |
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| Description | Noradrenaline (BAN) (abbreviated NA or NAd) or norepinephrine (INN) (abbreviated norepi or NE) is a catecholamine with dual roles as a hormone and a neurotransmitter.; Noradrenaline 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 antagonising alpha-1 and alpha-2 receptors and causing a resultant increase in systemic vascular resistance.; Norepinephrine is a catecholamine and a phenethylamine. The natural stereoisomer is L-(?)-(R)-norepinephrine. The prefix nor-, is derived from the German abbreviation for "N ohne Radikal" (N, the symbol for nitrogen, without radical), referring to the absence of the methyl functional group at the nitrogen atom.; Norepinephrine, along with dopamine, has come to be recognized as playing a large role in attention and focus. For people with ADHD, psychostimulant medications such as methylphenidate (Ritalin/Concerta), dextroamphetamine (Dexedrine), and Adderall (a mixture of dextroamphetamine and racemic amphetamine salts) are prescribed to help increase levels of norepinephrine and dopamine. Atomoxetine (Strattera) is a selective norepinephrine reuptake inhibitor, and is a unique 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 ADHD. Consulting with a physician, physician assistant 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 ADHD.); Precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic.; ?-methyltyrosine is a substance that intervenes in norepinephrine synthesis by substituting tyrosine for tyrosine hydroxylase, and blocking this enzyme. Norepinephrine is elevated in the urine of people who consume bananas.
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| CAS Number | 51-41-2 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | Not Available |
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| Chemical Formula | C8H11NO3 |
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| IUPAC name | |
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| InChI Identifier | InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2 |
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| InChI Key | SFLSHLFXELFNJZ-UHFFFAOYSA-N |
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| Isomeric SMILES | NCC(O)C1=CC(O)=C(O)C=C1 |
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| Average Molecular Weight | 169.1778 |
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| Monoisotopic Molecular Weight | 169.073893223 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Phenols |
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| Sub Class | Benzenediols |
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| Direct Parent | Catechols |
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| Alternative Parents | |
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| Substituents | - Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Monocyclic benzene moiety
- 1,2-aminoalcohol
- Secondary alcohol
- Organic nitrogen compound
- Aromatic alcohol
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Alcohol
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties - Experimental |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 56.80%; H 6.55%; N 8.28%; O 28.37% | DFC |
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| Melting Point | Mp 216.5-218° | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | -1.24 | HANSCH,C ET AL. (1995) |
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| Experimental pKa | pKa3 12 (25°) | DFC |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | [a]25D -37.3 | DFC |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | Not Available |
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| MS/MS | Not Available |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 388394 |
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| ChEMBL ID | CHEMBL1437 |
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| KEGG Compound ID | C00547 |
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| Pubchem Compound ID | 439260 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 18357 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | DB00368 |
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| HMDB ID | HMDB00216 |
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| CRC / DFC (Dictionary of Food Compounds) ID | BLS56-O:BLS57-P |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | NORADRENALIN|L-NORADRENALINE|NOREPINEPHRINE |
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| BIGG ID | 35313 |
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| KNApSAcK ID | C00001424 |
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| HET ID | LNR |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Norepinephrine |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| adrenergic | 37962 | Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter. | DUKE | | anti shock | | | DUKE | | hypertensive | | | DUKE | | inotropic | | | DUKE | | neurotransmitter | 25512 | An endogenous compound that is used to transmit information across the synapse between a neuron and another cell. | DUKE | | sympathomimetic | 35524 | A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. | DUKE | | vasoconstrictor | 50514 | Drug used to cause constriction of the blood vessels. | DUKE |
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| Enzymes | | Name | Gene Name | UniProt ID |
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| Alpha-2A adrenergic receptor | ADRA2A | P08913 | | Alpha-2B adrenergic receptor | ADRA2B | P18089 | | Phenylalanine-4-hydroxylase | PAH | P00439 | | Glycerol kinase | GK | P32189 | | Beta-1 adrenergic receptor | ADRB1 | P08588 | | Beta-2 adrenergic receptor | ADRB2 | P07550 |
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| Pathways | |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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