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Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO3
Molecular Weight 183.2048
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACEPINEPHRINE

SMILES

CNCC(c1ccc(c(c1)O)O)O

InChI

InChIKey=UCTWMZQNUQWSLP-UHFFFAOYSA-N
InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3

HIDE SMILES / InChI

Molecular Formula C9H13NO3
Molecular Weight 183.2048
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

For temporary relief of mild symptoms of intermittent asthma: wheezing, tightness of chest, shortness of breath
Palliative
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unknown, 2 years
n = 1
Health Status: unknown
Age Group: 2 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Hypertension, Tachycardia...
AEs leading to
discontinuation/dose reduction:
Hypertension (5.4%)
Tachycardia (5.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypertension 5.4%
Disc. AE
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unknown, 2 years
n = 1
Health Status: unknown
Age Group: 2 years
Sex: M
Population Size: 1
Sources:
Tachycardia 5.4%
Disc. AE
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unknown, 2 years
n = 1
Health Status: unknown
Age Group: 2 years
Sex: M
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Structural basis of beta-adrenergic receptor subtype specificity studied with chimeric beta 1/beta 2-adrenergic receptors.
1988 Dec
Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor.
1993 Dec
Carazolol: a potent, selective beta 3-adrenoceptor agonist.
1995 Nov 30
Ligand efficacy and potency at recombinant alpha2 adrenergic receptors: agonist-mediated [35S]GTPgammaS binding.
1998 Apr 1
A sensitive and selective spectrophotometric estimation of catechol derivatives in pharmaceutical preparations.
2001 Dec 24
[Experimental study of puerarin injection on the hemorheology in acute blood-stasis model rats].
2003 Dec
[Surface architectonics and cytoskeleton of erythrocytes and their modulation by adrenergic agents in patients with bronchial asthma].
2004
Long-term stability study of L-adrenaline injections: Kinetics of sulfonation and racemization pathways of drug degradation.
2004 Apr
Stereospecificity of horseradish peroxidase.
2004 Dec
Cardiovascular responses of Chinook salmon (Oncorhynchus tshawytscha) during rapid anaesthetic induction and recovery.
2004 Feb
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.
2004 Feb
Extravasation of blood-borne immunoglobulin G through blood-brain barrier during adrenaline-induced transient hypertension in the rat.
2004 Jun
MAPK-dependent regulation of IL-1- and beta-adrenoreceptor-induced inflammatory cytokine production from mast cells: implications for the stress response.
2004 Sep 21
Catecholamines potentiate the effect of thyroid hormone on intestinal absorption of glucose in the rat.
2005 Jun
Plasma levobupivacaine concentrations following scalp block in patients undergoing awake craniotomy.
2005 Jun
Single dose oral clonidine premedication does not enhance postoperative, single low dose epidural morphine analgesia in hysterectomy patients.
2005 Mar
Proinflammatory cytokine responses induced by influenza A (H5N1) viruses in primary human alveolar and bronchial epithelial cells.
2005 Nov 11
Opposite changes in imidazoline I2 receptors and alpha2-adrenoceptors density in rat frontal cortex after induced gliosis.
2005 Nov 26
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 Oct
Method development for the enantiomeric purity determination of low concentrations of adrenaline in local anaesthetic solutions by capillary electrophoresis.
2006 Apr 11
[Adrenaline].
2006 Aug-Sep
[Experimental studies of rhizoma Astilbes chinensis on its effects in abirritation, blood activation, cough relieving and sputum elimination].
2006 Dec
Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978.
2006 Jan
[European Resuscitation Council guidelines for cardiopulmonary resuscitation in 2005].
2006 Jan-Feb
Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors.
2006 Sep
Extracellular signal-regulated kinase 1/2-mediated transcriptional regulation of G-protein-coupled receptor kinase 3 expression in neuronal cells.
2007 Apr
More PKA independent beta-adrenergic signalling via cAMP: is Rap1-mediated glucose uptake in vascular smooth cells physiologically important?
2007 Jun
Stereospecificity of mushroom tyrosinase immobilized on a chiral and a nonchiral support.
2007 May 30
End-column chemiluminescence detection for pressurized capillary electrochromatographic analysis of norepinephrine and epinephrine.
2007 Nov 2
Targeting multiple dyslipidemias with fixed combinations--focus on extended release niacin and simvastatin.
2008
Optimal vasopressor drug therapy during resuscitation.
2008
Analysis of the antimicrobial activity of local anaesthetics used for dental analgesia.
2008 Jan
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 Jan
Electrical nerve stimulation or ultrasound guidance for lateral sagittal infraclavicular blocks: a randomized, controlled, observer-blinded, comparative study.
2008 Jun
Analysis of efficacy of chiral adrenergic agonists.
2008 Mar
The methylation, neurotransmitter, and antioxidant connections between folate and depression.
2008 Sep
Caffeine and anaerobic performance: ergogenic value and mechanisms of action.
2009
Adrenaline-induced chronic ocular hypertension in adult rabbits.
2009 Apr
Simultaneous separation of epinephrine and norepinephrine enantiomers by EKC: application to the analysis of pharmaceutical formulations.
2009 Aug
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 Aug 4
Characteristics and outcome of cardiopulmonary resuscitation in hospitalised African children.
2009 Jan
The impact of platelet function or C-reactive protein, on cardiovascular events after an acute myocardial infarction.
2009 Jul 7
Enhanced voltammetric detection of epinephrine at a carbon nanotube/nafion composite electrode in the presence of ascorbic acid.
2009 Nov
Trocar-guided total tension-free vaginal mesh repair of post-hysterectomy vaginal vault prolapse.
2009 Oct
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 Sep
High concentrations of dexmedetomidine inhibit compound action potentials in frog sciatic nerves without alpha(2) adrenoceptor activation.
2010 Aug
Job insecurity and change over time in health among older men and women.
2010 Jan
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 Jul
Intraoperative chemotherapy with cisplatin and epinephrine after cytoreductive surgery in patients with recurrent ovarian cancer: a phase I study.
2010 Mar
A comparative study of intrathecal and epidural buprenorphine using combined spinal-epidural technique for caesarean section.
2010 May
Patents

Sample Use Guides

Bronchiolitis: 0,1ml<5kg, 0,15ml 5-6,9kg, 0,20ml 7-9,9kg, 0,25ml >10kg of racemic adrenaline (racepinephrine) 20mg/ml diluted in 2ml NaCl. Maximum 12 inhalations/24 hours
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:36:56 UTC 2021
Edited
by admin
on Sat Jun 26 02:36:56 UTC 2021
Record UNII
GR0L9S3J0F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RACEPINEPHRINE
USP  
Common Name English
2-(METHYLAMINO)-1-(3,4-DIHYDROXYPHENYL)ETHANOL
Systematic Name English
DL-ADRENALINE
Common Name English
EPINEPHRINE, DL-
Common Name English
BENZYL ALCOHOL, 3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, (+/-)-
Systematic Name English
EPIRENAMINE
Common Name English
EPINEPHRINE DL-FORM
MI  
Common Name English
1,2-BENZENEDIOL, 4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-
Systematic Name English
RACEPINEFRINE [WHO-DD]
Common Name English
RACEPINEFRINE [INN]
Common Name English
EPINEPHRINE DL-FORM [MI]
Common Name English
EPINEPHRINE RACEMIC
Common Name English
1-(3,4-DIHYDROXY)PHENYL-2-METHYLAMINOETHANOL
Common Name English
RACEPINEPHRINE [USP]
Common Name English
RACEPINEFRINE
INN   WHO-DD  
INN  
Official Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
Code System Code Type Description
RXCUI
66887
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY RxNorm
INN
4553
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
CAS
8059-19-6
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
SUPERSEDED
ChEMBL
CHEMBL1740
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
EVMPD
SUB10238MIG
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
DRUG CENTRAL
4508
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-347-6
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
NCI_THESAURUS
C76546
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
DRUG BANK
DB11124
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
CAS
329-65-7
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
MERCK INDEX
M4944
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY Merck Index
CAS
6912-68-1
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
SUPERSEDED
CAS
8060-13-7
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
SUPERSEDED
PUBCHEM
838
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
FDA UNII
GR0L9S3J0F
Created by admin on Sat Jun 26 02:36:56 UTC 2021 , Edited by admin on Sat Jun 26 02:36:56 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY