Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C9H13NO3.ClH |
| Molecular Weight | 219.665 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CNCC(O)C1=CC(O)=C(O)C=C1
InChI
InChIKey=ATADHKWKHYVBTJ-UHFFFAOYSA-N
InChI=1S/C9H13NO3.ClH/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;/h2-4,9-13H,5H2,1H3;1H
| Molecular Formula | C9H13NO3 |
| Molecular Weight | 183.2044 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Racepinephrine or racemic epinephrine is a mixture of levo and dextro isomers of epinephrine act as a nonselective agonist at adrenergic receptors. It is a bronchodilator used in the temporary relief of mild symptoms of intermittent asthma including wheezing, shortness of breath. Inhaled racepinephrine became available in September 2012 as a nonprescription treatment for bronchospasm based on a 1986 US Food and Drug Administration rule. Besides, racemic epinephrine relieves respiratory distress in hospitalized infants with bronchiolitis and is safe but does not abbreviate hospital stay. Morbidity associated with bronchiolitis as identified by parents persists for at least one week after hospital discharge in most infants.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2331074 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Unknown Approved UseFor temporary relief of mild symptoms of intermittent asthma: wheezing, tightness of chest, shortness of breath |
|||
| Palliative | Unknown Approved UseUnknown |
Doses
| Dose | Population | Adverse events |
|---|---|---|
50 mg single, oral Overdose |
unknown, 2 years |
Disc. AE: Hypertension, Tachycardia... AEs leading to discontinuation/dose reduction: Hypertension (5.4%) Sources: Tachycardia (5.4%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Hypertension | 5.4% Disc. AE |
50 mg single, oral Overdose |
unknown, 2 years |
| Tachycardia | 5.4% Disc. AE |
50 mg single, oral Overdose |
unknown, 2 years |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Vesicular monoamine transporters (VMATs) in adrenal chromaffin cells: stress-triggered induction of VMAT2 and expression in epinephrine synthesizing cells. | 2010-11 |
|
| [Experimental study on effect of pre-acupuncture and moxibustion on molecular markers in pre-thrombosis state of rats]. | 2010-10 |
|
| High concentrations of dexmedetomidine inhibit compound action potentials in frog sciatic nerves without alpha(2) adrenoceptor activation. | 2010-08 |
|
| Calcium deficiency in the early stages after weaning is associated with the enhancement of a low level of adrenaline-stimulated lipolysis and reduction of adiponectin release in isolated rat mesenteric adipocytes. | 2010-07 |
|
| A comparative study of intrathecal and epidural buprenorphine using combined spinal-epidural technique for caesarean section. | 2010-05 |
|
| Intraoperative chemotherapy with cisplatin and epinephrine after cytoreductive surgery in patients with recurrent ovarian cancer: a phase I study. | 2010-03 |
|
| Job insecurity and change over time in health among older men and women. | 2010-01 |
|
| Enhanced voltammetric detection of epinephrine at a carbon nanotube/nafion composite electrode in the presence of ascorbic acid. | 2009-11 |
|
| Trocar-guided total tension-free vaginal mesh repair of post-hysterectomy vaginal vault prolapse. | 2009-10 |
|
| Activation of AMP-activated protein kinase by interleukin-6 in rat skeletal muscle: association with changes in cAMP, energy state, and endogenous fuel mobilization. | 2009-09 |
|
| Simultaneous determination of epinephrine, uric acid and xanthine in the presence of ascorbic acid using an ultrathin polymer film of 5-amino-1,3,4-thiadiazole-2-thiol modified electrode. | 2009-08-04 |
|
| Simultaneous separation of epinephrine and norepinephrine enantiomers by EKC: application to the analysis of pharmaceutical formulations. | 2009-08 |
|
| The impact of platelet function or C-reactive protein, on cardiovascular events after an acute myocardial infarction. | 2009-07-07 |
|
| Adrenaline-induced chronic ocular hypertension in adult rabbits. | 2009-04 |
|
| Characteristics and outcome of cardiopulmonary resuscitation in hospitalised African children. | 2009-01 |
|
| Caffeine and anaerobic performance: ergogenic value and mechanisms of action. | 2009 |
|
| The methylation, neurotransmitter, and antioxidant connections between folate and depression. | 2008-09 |
|
| Electrical nerve stimulation or ultrasound guidance for lateral sagittal infraclavicular blocks: a randomized, controlled, observer-blinded, comparative study. | 2008-06 |
|
| Analysis of efficacy of chiral adrenergic agonists. | 2008-03 |
|
| Analysis of the antimicrobial activity of local anaesthetics used for dental analgesia. | 2008-01 |
|
| Neuronal nitric oxide synthase gene inactivation reduces the expression of vasopressin in the hypothalamic paraventricular nucleus and of catecholamine biosynthetic enzymes in the adrenal gland of the mouse. | 2008-01 |
|
| Targeting multiple dyslipidemias with fixed combinations--focus on extended release niacin and simvastatin. | 2008 |
|
| Optimal vasopressor drug therapy during resuscitation. | 2008 |
|
| N,N-Bis(2-bromo-ethyl)aniline. | 2007-12-06 |
|
| End-column chemiluminescence detection for pressurized capillary electrochromatographic analysis of norepinephrine and epinephrine. | 2007-11-02 |
|
| More PKA independent beta-adrenergic signalling via cAMP: is Rap1-mediated glucose uptake in vascular smooth cells physiologically important? | 2007-06 |
|
| Stereospecificity of mushroom tyrosinase immobilized on a chiral and a nonchiral support. | 2007-05-30 |
|
| Extracellular signal-regulated kinase 1/2-mediated transcriptional regulation of G-protein-coupled receptor kinase 3 expression in neuronal cells. | 2007-04 |
|
| [Experimental studies of rhizoma Astilbes chinensis on its effects in abirritation, blood activation, cough relieving and sputum elimination]. | 2006-12 |
|
| [Adrenaline]. | 2006-10-14 |
|
| Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors. | 2006-09 |
|
| [European Resuscitation Council guidelines for cardiopulmonary resuscitation in 2005]. | 2006-04-28 |
|
| Method development for the enantiomeric purity determination of low concentrations of adrenaline in local anaesthetic solutions by capillary electrophoresis. | 2006-04-11 |
|
| Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978. | 2006-01 |
|
| Opposite changes in imidazoline I2 receptors and alpha2-adrenoceptors density in rat frontal cortex after induced gliosis. | 2005-11-26 |
|
| Proinflammatory cytokine responses induced by influenza A (H5N1) viruses in primary human alveolar and bronchial epithelial cells. | 2005-11-11 |
|
| Characterization of porcine beta1- and beta2-adrenergic receptors in heart, skeletal muscle, and adipose tissue, and the identification of an atypical beta-adrenergic binding site. | 2005-10 |
|
| Catecholamines potentiate the effect of thyroid hormone on intestinal absorption of glucose in the rat. | 2005-06 |
|
| Plasma levobupivacaine concentrations following scalp block in patients undergoing awake craniotomy. | 2005-06 |
|
| Single dose oral clonidine premedication does not enhance postoperative, single low dose epidural morphine analgesia in hysterectomy patients. | 2005-03 |
|
| Transfusion-free pediatric burn surgery: techniques and strategies. | 2005-02 |
|
| Stereospecificity of horseradish peroxidase. | 2004-12 |
|
| MAPK-dependent regulation of IL-1- and beta-adrenoreceptor-induced inflammatory cytokine production from mast cells: implications for the stress response. | 2004-09-21 |
|
| Extravasation of blood-borne immunoglobulin G through blood-brain barrier during adrenaline-induced transient hypertension in the rat. | 2004-06 |
|
| [Experimental study of puerarin injection on the hemorheology in acute blood-stasis model rats]. | 2003-12 |
|
| A sensitive and selective spectrophotometric estimation of catechol derivatives in pharmaceutical preparations. | 2001-12-24 |
|
| Ligand efficacy and potency at recombinant alpha2 adrenergic receptors: agonist-mediated [35S]GTPgammaS binding. | 1998-04-01 |
|
| Carazolol: a potent, selective beta 3-adrenoceptor agonist. | 1995-11-30 |
|
| Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor. | 1993-12 |
|
| Structural basis of beta-adrenergic receptor subtype specificity studied with chimeric beta 1/beta 2-adrenergic receptors. | 1988-12 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:28:37 GMT 2025
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on
Mon Mar 31 18:28:37 GMT 2025
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| Record UNII |
336096P2WE
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C319
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CFR |
21 CFR 341.16
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m4944
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C73826
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DTXSID9057717
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SUB33967
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| Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ENANTIOMER -> RACEMATE |
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IMPURITY -> PARENT |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |