Epinephrine,(±)-

US Approved OTC

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H13NO3
Molecular Weight	183.2044
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNCC(O)C1=CC=C(O)C(O)=C1

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	183.2044
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5c6d98fe-3e86-4816-92f2-49d38a432e39&type=display | https://www.ncbi.nlm.nih.gov/pubmed/23758233 | https://www.ncbi.nlm.nih.gov/pubmed/25213051

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
Adrenergic receptor 35 Target ID: CHEMBL2331074 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22220172	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5c6d98fe-3e86-4816-92f2-49d38a432e39&type=display	Palliative		Approved 8583	Unknown Approved Use For temporary relief of mild symptoms of intermittent asthma: wheezing, tightness of chest, shortness of breath
Bronchiolitis 3 Sources: https://clinicaltrials.gov/show/NCT00817466	Palliative		Approved 8583	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
50 mg single, oral Overdose Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7781638/	unknown, 2 years Health Status: unknown Age Group: 2 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7781638/	Disc. AE: Hypertension, Tachycardia... AEs leading to discontinuation/dose reduction: Hypertension (5.4%) Tachycardia (5.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/7781638/

AEs

AE	Significance	Dose	Population
Hypertension	5.4% Disc. AE	50 mg single, oral Overdose Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7781638/	unknown, 2 years Health Status: unknown Age Group: 2 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7781638/
Tachycardia	5.4% Disc. AE	50 mg single, oral Overdose Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7781638/	unknown, 2 years Health Status: unknown Age Group: 2 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7781638/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY548872	https://www.001chemical.com/chem/329-65-7
001 Chemical	DY557482	https://www.001chemical.com/chem/51-42-3
001 Chemical	DY580639	https://www.001chemical.com/chem/929881-05-0
3B Scientific (Wuhan) Corp	3B1-01643	http://www.3bsc.com/index/pro_info.php?id=21855
AA Blocks	AA019FXR	https://www.aablocks.com/goods/Goods/detail?id=AA019FXR
Aaron Chemicals	AR019GPJ	http://www.aaronchem.com/329-65-7
AbMole Bioscience	M5586	http://www.abmole.com/products/dl-epinephrine.html
Acadechem	ACDS-023900	http://www.acadechemical.com/product/98599
Achemo Scientific Limited	AC-11419	http://www.achemo.com/product_view.asp?ID=1309
Achemtek	0104-000882	http://www.achemtek.com/329-65-7
AHH Chemical co.,ltd	MR-1003006	http://www.ahhchemical.com/product/MR-1003006.html
AK Scientific, Inc. (AKSCI)	70618	http://www.aksci.com/item_detail.php?cat=70618
Allbio Pharm Co., Ltd	AD14333	http://www.allbiopharm.com/product/n/AD14333
Angene	AGN-PC-03GAD8	http://www.angenechemical.com/productshow/AGN-PC-03GAD8.html
Angene	AGN-PC-0OBI98	http://www.angenechemical.com/productshow/AGN-PC-0OBI98.html
Anward	ANW-71524	http://www.anward.com/pro_result/57975
Aurora Fine Chemicals LLC	K02.873.950	http://online.aurorafinechemicals.com/info?ID=K02.873.950
Aurum Pharmatech LLC	M-2547	http://www.Aurumpharmatech.com/Product/ProductDetails/M_2547
BioChemPartner	BCP17220	http://www.biochempartner.com/329-65-7-BCP17220
BioCrick	BCC4318	http://www.biocrick.com/DL-Adrenaline-BCC4318.html
BioCrick	BCN2191	http://www.biocrick.com/Adrenaline-BCN2191.html
BioSynth	J-018952	https://www.biosynth.com/en/products/all-products/products/J-018952.html
BOC Sciences	1189977-29-4	https://www.bocsci.com/epinephrine-d3-cas-1189977-29-4-item-306851.html
BOC Sciences	1219803-77-6	https://www.bocsci.com/epinephrine-d6-cas-1219803-77-6-item-306852.html
Chem Scene	CS-2556	http://www.chemscene.com/329-65-7.html
ChemMol	30101990	http://www.chemmol.com/chemmol/30101990.html
ChemMol	44022333	http://www.chemmol.com/chemmol/44022333.html
ChemMol	49409605	http://www.chemmol.com/chemmol/49409605.html
ChemMol	49416189	http://www.chemmol.com/chemmol/49416189.html
Chemspace	CSSB00000028532	https://chem-space.com/CSSB00000028532
Clearsynth	CS-CX-00056	https://www.clearsynth.com/en/CSCX00056.html
Clearsynth	CS-EG-00043	https://www.clearsynth.com/en/CSEG00043.html
Clearsynth	CS-ER-02372	https://www.clearsynth.com/en/CSER02372.html
Clearsynth	CS-O-02818	https://www.clearsynth.com/en/CSO02818.html
DC Chemicals	DC34172	http://www.dcchemicals.com//product_show-DL-Adrenaline.html
DC Chemicals	DC37693	http://www.dcchemicals.com//product_show-D-Epinephrine.html
eNovation Chemicals	D670854	https://www.enovationchem.com/ProductDetails.asp?ProductID=D670854
Finetech	FT-0625455	http://www.finetechnology-ind.com/prod/detail/pub/329-65-7.html
Finetech	FT-0695432	http://www.finetechnology-ind.com/prod/detail/pub/6912-68-1.html
Hairui	HR138456	http://www.hairuichem.com/en/product/329-65-7.html
iChemical	EBD2204189	http://www.ichemical.com/products/329-65-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00227160	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00227160
LGC Standards	MM0614.15	https://www.lgcstandards.com/US/en/p/MM0614.15
mcule	MCULE-4868062157	https://mcule.com/MCULE-4868062157/
MedChem Express	HY-B0447	https://www.medchemexpress.com/DL-Epinephrine.html
Molcore	MC548872	https://www.molcore.com/product/329-65-7
Molcore	MC557482	https://www.molcore.com/product/51-42-3
Molcore	MC580639	https://www.molcore.com/product/929881-05-0
MolPort	MolPort-001-785-704	https://www.molport.com/shop/molecule-link/MolPort-001-785-704
MuseChem	A000274	https://www.musechem.com/product/A000274.html
MuseChem	A000523	https://www.musechem.com/product/A000523.html
Oakwood	234223	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=115222&ExtHyperLink=1
OChem	116	http://www.ocheminc.com/index.php?act=psearch&pid=329A657
Parchem	28119	http://www.parchem.com/chemical-supplier-distributor/Adrenaline-018119.aspx
Selleck Chemicals	S2523	http://www.selleckchem.com/products/dl-adrenaline.html
Sigma-Aldrich	E-077_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/e077?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	E1635_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/e1635?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S008243	http://www.sinfoobiotech.com/product/1011641
Smolecule	S525667	http://www.smolecule.com/products/s525667
Smolecule	S526376	http://www.smolecule.com/products/s526376
TCI (Tokyo Chemical Industry)	A0172	http://www.tcichemicals.com/eshop/en/us/commodity/A0172/index.html
THE BioTek	bt-265790	https://www.thebiotek.com/product/inhibitors/bt-265790
THE BioTek	bt-266826	https://www.thebiotek.com/product/inhibitors/bt-266826

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	21046458
[Experimental study on effect of pre-acupuncture and moxibustion on molecular markers in pre-thrombosis state of rats].	2010-10	21058484
High concentrations of dexmedetomidine inhibit compound action potentials in frog sciatic nerves without alpha(2) adrenoceptor activation.	2010-08	20649570
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	20015519
A comparative study of intrathecal and epidural buprenorphine using combined spinal-epidural technique for caesarean section.	2010-05	20885865
Intraoperative chemotherapy with cisplatin and epinephrine after cytoreductive surgery in patients with recurrent ovarian cancer: a phase I study.	2010-03	20032778
Job insecurity and change over time in health among older men and women.	2010-01	19934165
Enhanced voltammetric detection of epinephrine at a carbon nanotube/nafion composite electrode in the presence of ascorbic acid.	2009-11	19908573
Trocar-guided total tension-free vaginal mesh repair of post-hysterectomy vaginal vault prolapse.	2009-10	19499156
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	19502419
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	19576392
Simultaneous separation of epinephrine and norepinephrine enantiomers by EKC: application to the analysis of pharmaceutical formulations.	2009-08	19650051
The impact of platelet function or C-reactive protein, on cardiovascular events after an acute myocardial infarction.	2009-07-07	19583836
Adrenaline-induced chronic ocular hypertension in adult rabbits.	2009-04	19384793
Characteristics and outcome of cardiopulmonary resuscitation in hospitalised African children.	2009-01	19013705
Caffeine and anaerobic performance: ergogenic value and mechanisms of action.	2009	19757860
The methylation, neurotransmitter, and antioxidant connections between folate and depression.	2008-09	18950248
Electrical nerve stimulation or ultrasound guidance for lateral sagittal infraclavicular blocks: a randomized, controlled, observer-blinded, comparative study.	2008-06	18499631
Analysis of efficacy of chiral adrenergic agonists.	2008-03	18172836
Analysis of the antimicrobial activity of local anaesthetics used for dental analgesia.	2008-01	18065672
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	17853069
Targeting multiple dyslipidemias with fixed combinations--focus on extended release niacin and simvastatin.	2008	19183748
Optimal vasopressor drug therapy during resuscitation.	2008	18394182
N,N-Bis(2-bromo-ethyl)aniline.	2007-12-06	21200963
End-column chemiluminescence detection for pressurized capillary electrochromatographic analysis of norepinephrine and epinephrine.	2007-11-02	17905257
More PKA independent beta-adrenergic signalling via cAMP: is Rap1-mediated glucose uptake in vascular smooth cells physiologically important?	2007-06	17450171
Stereospecificity of mushroom tyrosinase immobilized on a chiral and a nonchiral support.	2007-05-30	17488091
Extracellular signal-regulated kinase 1/2-mediated transcriptional regulation of G-protein-coupled receptor kinase 3 expression in neuronal cells.	2007-04	17255468
[Experimental studies of rhizoma Astilbes chinensis on its effects in abirritation, blood activation, cough relieving and sputum elimination].	2006-12	17357557
[Adrenaline].	2006-10-14	17037442
Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors.	2006-09	16944458
[European Resuscitation Council guidelines for cardiopulmonary resuscitation in 2005].	2006-04-28	16640220
Method development for the enantiomeric purity determination of low concentrations of adrenaline in local anaesthetic solutions by capillary electrophoresis.	2006-04-11	16303275
Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978.	2006-01	16502872
Opposite changes in imidazoline I2 receptors and alpha2-adrenoceptors density in rat frontal cortex after induced gliosis.	2005-11-26	16107261
Proinflammatory cytokine responses induced by influenza A (H5N1) viruses in primary human alveolar and bronchial epithelial cells.	2005-11-11	16283933
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	16160045
Catecholamines potentiate the effect of thyroid hormone on intestinal absorption of glucose in the rat.	2005-06	16749344
Plasma levobupivacaine concentrations following scalp block in patients undergoing awake craniotomy.	2005-06	15817709
Single dose oral clonidine premedication does not enhance postoperative, single low dose epidural morphine analgesia in hysterectomy patients.	2005-03	15962644
Transfusion-free pediatric burn surgery: techniques and strategies.	2005-02	15655467
Stereospecificity of horseradish peroxidase.	2004-12	15653431
MAPK-dependent regulation of IL-1- and beta-adrenoreceptor-induced inflammatory cytokine production from mast cells: implications for the stress response.	2004-09-21	15383152
Extravasation of blood-borne immunoglobulin G through blood-brain barrier during adrenaline-induced transient hypertension in the rat.	2004-06	15204054
[Experimental study of puerarin injection on the hemorheology in acute blood-stasis model rats].	2003-12	15617506
A sensitive and selective spectrophotometric estimation of catechol derivatives in pharmaceutical preparations.	2001-12-24	18968454
Ligand efficacy and potency at recombinant alpha2 adrenergic receptors: agonist-mediated [35S]GTPgammaS binding.	1998-04-01	9605427
Carazolol: a potent, selective beta 3-adrenoceptor agonist.	1995-11-30	8719421
Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor.	1993-12	7903415
Structural basis of beta-adrenergic receptor subtype specificity studied with chimeric beta 1/beta 2-adrenergic receptors.	1988-12	2849109

Patents

Sample Use Guides

In Vivo Use Guide

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 `Wed Apr 02 08:41:36 GMT 2025` Edited by `admin` on `Wed Apr 02 08:41:36 GMT 2025`
Record UNII	GR0L9S3J0F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Epinephrine,(±)-

Common Name

English

RACEPINEFRINE

Preferred Name

English

2-(METHYLAMINO)-1-(3,4-DIHYDROXYPHENYL)ETHANOL

Systematic Name

English

RACEPINEPHRINE [USP MONOGRAPH]

Common 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

Common Name

English

1,2-BENZENEDIOL, 4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-

Systematic Name

English

(±)-Epinephrine

Common Name

English

racepinefrine [INN]

Common Name

English

EPINEPHRINE DL-FORM [MI]

Common Name

English

RACEPINEPHRINE

Common Name

English

EPINEPHRINE RACEMIC

Common Name

English

1-(3,4-DIHYDROXY)PHENYL-2-METHYLAMINOETHANOL

Common Name

English

Racepinefrine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149