RACEPINEPHRINE

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(O)=C(O)C=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 33 Target ID: CHEMBL2331074 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22220172	Agonist 2637

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 234 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5c6d98fe-3e86-4816-92f2-49d38a432e39&type=display	Palliative		Approved 8307	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 8307	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 n = 1 Health Status: unknown Age Group: 2 years Sex: M Population Size: 1 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 n = 1 Health Status: unknown Age Group: 2 years Sex: M Population Size: 1 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 n = 1 Health Status: unknown Age Group: 2 years Sex: M Population Size: 1 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
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
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
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
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
BioChemPartner	BCP17220	http://www.biochempartner.com/329-65-7-BCP17220
BioCrick	BCN2191	http://www.biocrick.com/Adrenaline-BCN2191.html
BioCrick	BCC4318	http://www.biocrick.com/DL-Adrenaline-BCC4318.html
BioSynth	J-018952	https://www.biosynth.com/en/products/all-products/products/J-018952.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	DC37693	http://www.dcchemicals.com//product_show-D-Epinephrine.html
DC Chemicals	DC34172	http://www.dcchemicals.com//product_show-DL-Adrenaline.html
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
LGC Standards	MM0614.15	https://www.lgcstandards.com/US/en/p/MM0614.15
Lab Network	LN00227160	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00227160
MedChem Express	HY-B0447	https://www.medchemexpress.com/DL-Epinephrine.html
MolPort	MolPort-001-785-704	https://www.molport.com/shop/molecule-link/MolPort-001-785-704
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
MuseChem	A000274	https://www.musechem.com/product/A000274.html
MuseChem	A000523	https://www.musechem.com/product/A000523.html
OChem	116	http://www.ocheminc.com/index.php?act=psearch&pid=329A657
Oakwood	234223	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=115222&ExtHyperLink=1
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
eNovation Chemicals	D670854	https://www.enovationchem.com/ProductDetails.asp?ProductID=D670854
iChemical	EBD2204189	http://www.ichemical.com/products/329-65-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-4868062157	https://mcule.com/MCULE-4868062157/

PubMed

Title	Date	PubMed
Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor.	1993 Dec	7903415
Carazolol: a potent, selective beta 3-adrenoceptor agonist.	1995 Nov 30	8719421
Ligand efficacy and potency at recombinant alpha2 adrenergic receptors: agonist-mediated [35S]GTPgammaS binding.	1998 Apr 1	9605427
A comparison of effects measured with isotonic and isometric recording: II. Concentration-effect curves for physiological antagonists.	2001 Aug	11487520
The role of angiotensin II in regulating catecholamine secretion during hypoxia in rainbow trout Oncorhynchus mykiss.	2001 Dec	11809790
The calibre of the foramen of Panizza in Crocodylus porosus is variable and under adrenergic control.	2001 May	11409632
[Endoscopic mucosal resection of premalignant lesions of the upper gastrointestinal tract].	2001 Nov	11778151
Arginine inhibits hemostasis activation.	2001 Nov 15	11728528
Epinephrine reduces the sedative side effects of epidural sufentanil for labour analgesia.	2002 Jan	11782332
The efficacy of hemodynamic and T-wave criteria for detecting intravascular injection of epinephrine test dose in propofol-anesthetized adults.	2002 Mar	11867404
[Experimental study of puerarin injection on the hemorheology in acute blood-stasis model rats].	2003 Dec	15617506
Cardiovascular and autonomic responses to lower body negative pressure: do not explain gender differences in orthostatic tolerance.	2003 Feb	12664246
[Surface architectonics and cytoskeleton of erythrocytes and their modulation by adrenergic agents in patients with bronchial asthma].	2004	15108451
Cytotoxic effects of gingival retraction cords on human gingival fibroblasts in vitro.	2004 Apr	15089944
Long-term stability study of L-adrenaline injections: Kinetics of sulfonation and racemization pathways of drug degradation.	2004 Apr	14999733
Cardiovascular responses of Chinook salmon (Oncorhynchus tshawytscha) during rapid anaesthetic induction and recovery.	2004 Feb	15050928
Extravasation of blood-borne immunoglobulin G through blood-brain barrier during adrenaline-induced transient hypertension in the rat.	2004 Jun	15204054
MAPK-dependent regulation of IL-1- and beta-adrenoreceptor-induced inflammatory cytokine production from mast cells: implications for the stress response.	2004 Sep 21	15383152
Single dose oral clonidine premedication does not enhance postoperative, single low dose epidural morphine analgesia in hysterectomy patients.	2005 Mar	15962644
Opposite changes in imidazoline I2 receptors and alpha2-adrenoceptors density in rat frontal cortex after induced gliosis.	2005 Nov 26	16107261
[Experimental studies of rhizoma Astilbes chinensis on its effects in abirritation, blood activation, cough relieving and sputum elimination].	2006 Dec	17357557
Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978.	2006 Jan	16502872
Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors.	2006 Sep	16944458
Extracellular signal-regulated kinase 1/2-mediated transcriptional regulation of G-protein-coupled receptor kinase 3 expression in neuronal cells.	2007 Apr	17255468
N,N-Bis(2-bromo-ethyl)aniline.	2007 Dec 6	21200963
More PKA independent beta-adrenergic signalling via cAMP: is Rap1-mediated glucose uptake in vascular smooth cells physiologically important?	2007 Jun	17450171
End-column chemiluminescence detection for pressurized capillary electrochromatographic analysis of norepinephrine and epinephrine.	2007 Nov 2	17905257
Analysis of the antimicrobial activity of local anaesthetics used for dental analgesia.	2008 Jan	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 Jan	17853069
Analysis of efficacy of chiral adrenergic agonists.	2008 Mar	18172836
Caffeine and anaerobic performance: ergogenic value and mechanisms of action.	2009	19757860
Adrenaline-induced chronic ocular hypertension in adult rabbits.	2009 Apr	19384793
Simultaneous separation of epinephrine and norepinephrine enantiomers by EKC: application to the analysis of pharmaceutical formulations.	2009 Aug	19650051
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	19576392
The impact of platelet function or C-reactive protein, on cardiovascular events after an acute myocardial infarction.	2009 Jul 7	19583836
Enhanced voltammetric detection of epinephrine at a carbon nanotube/nafion composite electrode in the presence of ascorbic acid.	2009 Nov	19908573
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	19502419
Job insecurity and change over time in health among older men and women.	2010 Jan	19934165
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	20015519
Intraoperative chemotherapy with cisplatin and epinephrine after cytoreductive surgery in patients with recurrent ovarian cancer: a phase I study.	2010 Mar	20032778
A comparative study of intrathecal and epidural buprenorphine using combined spinal-epidural technique for caesarean section.	2010 May	20885865

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 `Sun Dec 18 19:37:39 UTC 2022` Edited by `admin` on `Sun Dec 18 19:37:39 UTC 2022`
Record UNII	GR0L9S3J0F
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

RACEPINEPHRINE

Common 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

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

RACEPINEFRINE

Official Name

English

Racepinefrine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149