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HCID 439260Erstellt: 27. Oktober 2026

Norepinephrin

NORADRENALINE · L-NORADRENALINE · NORADRENALIN · levophed · l-1-(3,4-dihydroxyphenyl)-2-aminoethanol · adrenor · aktamin · norartrinal

https://huagongshe.com/de/chemical/439260

Molekülstruktur von Norepinephrin

Identifikatoren & physikalische Daten

CAS No.51-41-2
SummenformelC8H11NO3
Durchschnittliche Molmasse169,18 g/mol
Monoisotopische Masse169,07389321 g/mol
SMILESNC[C@H](O)c1ccc(O)c(O)c1
InChIKeySFLSHLFXELFNJZ-QMMMGPOBSA-N
PubChem CID439260
ChEMBLCHEMBL1437
ChEBICHEBI:18357
EC No.200-096-6
DTXSIDDTXSID5023378
Lokaler NameNorepinephrin

Chemische & physikalische Eigenschaften

XLogP-1,2
Polarare Oberfläche (TPSA)86,7
H-Brücken-Donoren4
H-Brücken-Akzeptoren4
Frei drehbare Bindungen2
Schwere Atome12
Formalladung0
Komplexität142
ArzneimittelPharmaceuticals -> SympathomimeticsPharmaceuticals -> Listed in ZINC15
LogP (Verteilungskoeffizient)log Kow = -1.24-1.05
Color/FormColorless microcrystals
LöslichkeitSlightly soluble in water, ethanol, diethyl ethervery soluble in alkali, dilute hydrochloric acid849 mg/mLAqueous Acid (Slightly), DMSO (Slightly)Soluble in alkali and dilute hydrochloric acid. Slightly soluble in water, ethanol and diethyl ether.
Human DrugsBreast FeedingLactationMilk, HumanAdrenergic AgonistsAdrenergic Alpha-AgonistsCatecholaminesSympathomimeticsVasoconstrictor Agents
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Schmelzpunkt217 °C (decomposes)145.2 - 146.4 °C220-230°C
Optical RotationSpecific optical rotation: -37.3 deg at 25 °C/D (c = 5 in water with 1 equiv hydrochloric acid)
Physical DescriptionSolid
Dissociation Constants8.58pKa = 8.58 (conjugate acid)pKa1 = 8.64pKa2 = 9.70
Collision Cross Section128.52 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]132.6 Ų [M+H-H2O]+ [CCS Type: TW137.3 Ų [M+H-H2O]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]137.2 Ų [M-H2O+H]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]134.4 Ų [M-H]-
Siedepunkt298.46°C (rough estimate)
Dichte1.2435 (rough estimate)
Brechungsindex1.5100 (estimate)
Lagerbedingungen2-8°C
Aggregatzustandcrystalline
pKa (Säurekonstante)8.64(at 25℃)
Farbeoff-white to tan
Merck14,6695
BRN4231961
Henry-Konstante3.1×1013 mol/(m3Pa) at 25℃, HSDB (2015)
StabilitätStable, but may be light-sensitive. Incompatible with acids, bases, oxidizing agents. Store at -20℃.
InChI1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
InChIKeySFLSHLFXELFNJZ-QMMMGPOBSA-N
SMILESNC[C@H](O)c1ccc(O)c(O)c1
CAS Datenbank51-41-2(CAS DataBase Reference)
EPA chemische InformationenNorepinephrine (51-41-2)

Sicherheit & Vorschriften

GHS-EinstufungDangerH300 (97.9%): Fatal if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Weitere SicherheitsinformationenIMAP assessments - 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-, (R)-: Human health tier I assessment
BrandpotenzialThis material is assumed to be combustible. /Norepinephrine bitartrate/
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl norepinephrine bitartrate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Norepinephrine bitartrate/
Toxic Combustion ProductsEmits toxic fumes under fire conditions. /Norepinephrine bitartrate/
Hazard Classes and CategoriesAcute Tox. 2 (97.9%)
Skin, Eye, and Respiratory IrritationsEye, skin, ... and/or respiratory tract irritation. /Norepinephrine bitartrate/
BrandbekämpfungsverfahrenWater spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials. This material is assumed to be combustible. As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity. As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing. /Norepinephrine bitartrate/
LagerbedingungenStore at 20 deg to 25 °C (68 deg to 77 °F). ... Protect from light.
ReinigungsverfahrenWipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately-labelled container for disposal. Wash spill site. /Norepinephrine bitartrate/

Anwendungen & Verwendung

Verwenden

Norepinephrine is used for increasing cardiac constriction and for the necessary elevation of blood pressure after sharp decline, which can result from surgical intervention or trauma.

EntsorgungsverfahrenSRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
Preventive MeasuresSRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Personal Protective Equipment (PPE)Wear approved respiratory protection, chemically compatible gloves and protective clothing. /Norepinephrine bitartrate/
KörperbelastungIn eight cases of injection of norepinephrine into healthy volunteers age 22 to 26 years old, blood plasma samples contained a mean norepinephrine concentration of 0.48 ng/mL (control), 0.58 ng/mL (1 mg/kg ethanol), 0.85 ng/mL (24 ng/kg/min IV for 20 min), 1.22 ng/mL (24 ng/kg/min IV for 20 min, after 1 mg/kg ethanol), 1.26 ng/mL (48 ng/kg/min IV for 20 min), 1.76 ng/mL (48 ng/kg/min IV for 20 min, after 1 mg/kg ethanol), 2.06 ng/mL (90 ng/kg/min IV for 20 min), and 2.49 ng/mL (90 ng/kg/min IV for 20 min, after 1 mg/kg ethanol)(1).
TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
WechselwirkungenCyclopropane and halothane anesthetics increase cardiac autonomic irritability and therefore seem to sensitize the myocardium to the action of intravenously administered epinephrine or norepinephrine bitartrate injection. Hence, the use of norepinephrine bitartrate injection during cyclopropane and halothane anesthesia is generally considered contraindicated because of the risk of producing ventricular tachycardia or fibrillation.Enhanced pressor response may occur in patients taking monoamine oxidase (MAO) inhibitors owing to inhibition of neuronal metabolic degradation.Administration of furosemide or other diuretics may decrease arterial responsiveness to pressor drugs such as norepinephrine.Tricyclic antidepressants (e.g., imipramine), some antihistamines (especially diphenhydramine, tripelennamine, and dexchlorpheniramine), parenteral ergot alkaloids, guanethidine, or methyldopa may potentiate the pressor effects of norepinephrine, resulting in severe, prolonged hypertension. Norepinephrine should be given cautiously and in small doses to patients receiving these drugs. Potentiation may result from inhibition of tissue uptake of norepinephrine or by increased adrenoreceptor sensitivity to the drug. Monoamine oxidase (MAO) is one of the enzymes responsible for norepinephrine metabolism. Although some clinicians have reported that MAO inhibitors do not appear to potentiate the effects of norepinephrine to a clinically important extent, the manufacturer states that norepinephrine should be administered with extreme caution to patients receiving an MAO inhibitor because severe, prolonged hypertension may result.For more Interactions (Complete) data for Norepinephrine (8 total), please visit the HSDB record page.
Gesundheitliche AuswirkungenChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5.0(SRC), determined from a log Kow of -1.24(2) and a regression-derived equation(3), indicates that norepinephrine is expected to have very high mobility in soil(SRC). Values for pKa1 and pKa2 of 8.64 and 9.70, respectively(4), indicate that norepinephrine will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of norepinephrine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.2X10-19 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Norepinephrine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.5X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(7). Biodegradation data for norepinephrine were not available(SRC,2009).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5.0(SRC), determined from a log Kow of -1.24(2) and a regression-derived equation(3), indicates that norepinephrineis not expected to adsorb to suspended solids and sediment(SRC). Values for pKa1 and pKa2 of 8.64 and 9.70, respectively(4), indicate that norepinephrine will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data for norepinephrine were not available(SRC,2009).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), norepinephrine, which has an estimated vapor pressure of 7.5X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase norepinephrine may be removed from the air by wet or dry deposition(SRC). Norepinephrine is unstable in light and air, especially at neutral and alkaline pHoxidation to noradrenochrome occurs(3).
Unerwünschte WirkungenThe most common adverse effects of norepinephrine relate directly to the activation of α1 receptors. Additionally, norepinephrine infusions without appropriately treating hypovolemia can result in reduced end-organ perfusionthis can be detrimental as most patients who require infusions of norepinephrine already have poor oxygen delivery or utilization.
ExpositionspfadeEndogenous, Ingestion, Dermal (contact)
ToxizitätsübersichtSigns and Symptoms of OverdoseUremic toxins such as noradrenalin are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869). Norepinephrine functions as a peripheral vasoconstrictor by acting on alpha-adrenergic receptors. It is also an inotropic stimulator of the heart and dilator of coronary arteries as a result of it's activity at the beta-adrenergic receptors.
Signs and SymptomsAs a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.
Soil Adsorption/MobilityThe Koc of norepinephrine is estimated as 5.0(SRC), using a log Kow of -1.24(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that norepinephrine is expected to have very high mobility in soil. Values for pKa1 and pKa2 of 8.64 and 9.70, respectively(4), indicate that norepinephrine will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).
Natural Pollution SourcesNorepinephrine is a naturally occurring neurotransmitter in the periphery and in adrenergic neurons in the central nervous system, which is released from sympathetic nerve terminals(1).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Overdosage with norepinephrine may result in headache, severe hypertension, reflex bradycardia, marked increase in peripheral resistance, and decreased cardiac output. In case of accidental overdosage, as evidenced by excessive blood pressure elevation, discontinue norepinephrine until the condition of the patient stabilizes./SIGNS AND SYMPTOMS/ Overdoses or conventional doses in hypersensitive persons (e.g., hyperthyroid patients) cause severe hypertension with violent headache, photophobia, stabbing retrosternal pain, pallor, intense sweating, and vomiting./SIGNS AND SYMPTOMS/ Possible allergic reaction to material if inhaled, ingested or in contact with skin. /Norepinephrine bitartrate//CASE REPORTS/ The syndrome of symmetrical peripheral gangrene is characterised by distal ischaemic damage in two or more extremities, without large vessel obstruction. Four patients with bilateral pedal ischaemia are described and their haemodynamic profiles presented. In all four cases the syndrome developed in association with noradrenaline administration, sepsis and DIC, despite a high cardiac output and a low calculated systemic vascular resistance index. Early treatment with epoprostenol was instituted in the final case and was successful./OTHER TOXICITY INFORMATION/ A rare case of cardiac failure due to hypertensive crisis in pheochromocytoma in a 25-year-old young man is presented. In the Emergency Department the patient complained of persisting headache and vomitinghe was distressed but fully alert, his heart rate was 110 b/min and blood pressure 180/80 mmHg. Few hours after admission, the clinical course suddenly got worse with signs and symptoms of fatal cardiac shock (dyspnea, cyanosis, pulmonary edema, hypocontractility of left ventricle). Autopsy revealed a large tumor of the left adrenal gland. Histological examination confirmed macroscopic suspicion of pheochromocytoma. Catecholamine serum levels were analysed by high pressure liquid chromatography (HPLC) with electrochemical detection. The urine contained 35 ug/24 hr norepinephrine and 184 ug/24 hr epinephrine (normal range < or = 64 and < or = 36 ug/24 hr respectively). These laboratory findings impressively demonstrate that the tumor was active, secreting high levels of epinephrine. Cardiac failure due to an acute catecholamine-related hypertensive crisis was established as the cause of death.
F8-10-23
Wassergefährdungsklasse (WGK)3
UN-TransportnummerUN 2811 6.1/PG 2
Zollcode29225090
RTECS-Nr.DN5950000
R-Sätze (R)26/27/28-34-11-28
Toxizitätdni-hmn:oth 5800 nmol/L CNREA8 40,1414,80
GefahrensymboleT+,C,F
Sicherheitshinweise (S)28-36/37-45-36/37/39-26-16-20
Gefahrenklasse6.1Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 2 Oral
VerpackungsgruppeII
Lagerklasse6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Gefahrstoffdaten51-41-2(Hazardous Substances Data)