Ephedrine

US Approved OTC

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H15NO
Molecular Weight	165.2322
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN[C@@H](C)[C@H](O)C1=CC=CC=C1

InChI

InChIKey=KWGRBVOPPLSCSI-WPRPVWTQSA-N

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf | https://www.rcpe.ac.uk/sites/default/files/lee_0.pdf

Ephedrine (l-form) is an alkaloid, which was initially purified from Ephedra plant. The extract form Ephedra has been used in China for medicinal purposes for several thousand years. Ephedrine acts as an agonist at alpha- and beta-adrenergic receptors and indirectly causes the release of norepinephrine from sympathetic neurons. The drug crosses the blood brain barrier and stimulates the central nervous system. Ephedrine products are now banned in many countries, as they are a major source for the production of the addictive compound methamphetamine. FDA has approved ephedrine only for the treatment of clinically important hypotension occurring in the setting of anesthesia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Beta-2 adrenergic receptor 203 Target ID: P07550\|\|\|Q53GA6\|\|\|Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2678	0.36 µM [EC50]
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2678	4.95 null [pKi]
Beta-1 adrenergic receptor 158 Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2678	0.5 µM [EC50]
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2678	4.83 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anesthesia-induced hypotension 10 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Primary		Approved 8429	AKOVAZ Approved Use AKOVAZ injection is an alpha- and beta- adrenergic agonist and a norepinephrine-releasing agent that is indicated for the treatment of clinically important hypotension occurring in the setting of anesthesia. Launch Date 2016

C_max

Value	Dose	Co-administered	Analyte	Population
79.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/	22 mg single, oral dose: 22 mg route of administration: Oral experiment type: SINGLE co-administered:		EPHEDRINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
87.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/	11 mg 3 times / day multiple, oral dose: 11 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EPHEDRINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/	22 mg single, oral dose: 22 mg route of administration: Oral experiment type: SINGLE co-administered:		EPHEDRINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
6.69 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/	11 mg 3 times / day multiple, oral dose: 11 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EPHEDRINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
Achemtek	0104-020654	http://www.achemtek.com/299-42-3
Acorn PharmaTech	ACN-037777	http://www.acornpharmatech.com/
Aurora Fine Chemicals LLC	A17.887.833	http://online.aurorafinechemicals.com/info?ID=A17.887.833
BioSynth	J-500280	https://www.biosynth.com/en/products/all-products/products/J-500280.html
Capot Chemical	PubChem5778	http://www.capotchem.com/en/5778.htm
Chem Scene	CS-4802	http://www.chemscene.com/Ephedrine.html
ChemMol	99067321	http://www.chemmol.com/chemmol/99067321.html
MedChem Express	HY-B1195	http://www.medchemexpress.com/Ephedrine.html
OChem	2694	http://www.ocheminc.com/index.php?act=psearch&pid=299E423
Parchem	26857	http://www.parchem.com/chemical-supplier-distributor/Ephedrine-016857.aspx
Sigma-Aldrich	134910_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/134910?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S007941	http://www.smolecule.com/products/s007941
Smolecule	S527246	http://www.smolecule.com/products/s527246
THE BioTek	bt-255443	https://www.thebiotek.com/product/inhibitors/bt-255443
THE BioTek	bt-267449	https://www.thebiotek.com/product/inhibitors/bt-267449
iChemical	EBD2203043	http://www.ichemical.com/products/299-42-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-1217859840	https://mcule.com/MCULE-1217859840/

PubMed

Title	Date	PubMed
Pharmaceutical cost savings of treating obesity with weight loss medications.	1999 Nov	10574509
Olanzapine-induced urinary incontinence: treatment with ephedrine.	2000 Aug	10982206
Caffeine and exercise: metabolism, endurance and performance.	2001	11583104
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
The many faces of ecstasy.	2001 Apr	11317061
The effects of an increase of central blood volume before spinal anesthesia for cesarean delivery: a qualitative systematic review.	2001 Apr	11273939
Stimulatory effect of D-ephedrine on beta3-adrenoceptors in adipose tissue of rats.	2001 Apr 12	11474539
Mass spectrometric quantitation of chiral drugs by the kinetic method.	2001 Apr 15	11338581
Study on the chiral recognition of the enantiomers of ephedrine derivatives with neutral and sulfated heptakis(2,3-O-diacetyl)-beta-cyclodextrins using capillary electrophoresis, UV, nuclear magnetic resonance spectroscopy and mass spectrometry.	2001 Apr 20	11358226
Ondansetron versus dehydrobenzoperidol and metoclopramide for management of postoperative nausea in laparoscopic surgery patients.	2001 Apr-Jun	11394426
Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort.	2001 Aug	11512648
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section.	2001 Aug	11506099
Dose of prophylactic intravenous ephedrine during spinal anesthesia for cesarean section.	2001 Aug	11498318
Prevention and management of hypotension during spinal anaesthesia for elective Caesarean section: a survey of practice.	2001 Aug	11493248
Use of nonprescription weight loss products: results from a multistate survey.	2001 Aug 22-29	11509057
The trouble with fat-burner pills.	2001 Aug 27	11534484
[Cerebral infarction in a patient consuming MaHuang extract and guarana].	2001 Feb 3	11229306
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.	2001 Jan	11575417
NCAA study of substance use and abuse habits of college student-athletes.	2001 Jan	11176146
Should the angiotensin II antagonists be discontinued before surgery?	2001 Jan	11133595
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.	2001 Jan	11071707
Combined spinal and epidural anesthesia with low doses of intrathecal bupivacaine in women with severe preeclampsia: a preliminary report.	2001 Jan-Feb	11172511
Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat.	2001 Jan-Feb	11153535
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training.	2001 Jul	11583395
Reappearance of cardiac presynaptic sympathetic nerve terminals in the transplanted heart: correlation between PET using (11)C-hydroxyephedrine and invasively measured norepinephrine release.	2001 Jul	11438620
Determination of ephedrines in urine by gas chromatography-mass spectrometry.	2001 Jul 15	11486842
Perioperative bradycardia and asystole: relationship to vasovagal syncope and the Bezold-Jarisch reflex.	2001 Jun	11573596
Spinal anaesthesia for Caesarean section with bupivacaine 5 mg ml(-1) in glucose 8 or 80 mg ml(-1).	2001 Jun	11573587
Cold-syrup induced movement disorder.	2001 Jun	11437145
It's a rave new world: rave culture and illicit drug use in the young.	2001 Jun	11405616
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations.	2001 Jun	11377047
Venlafaxine occupation at the noradrenaline reuptake site: in-vivo determination in healthy volunteers.	2001 Mar	11277612
[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus].	2001 Mar 20	11332378
Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters by Mannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines.	2001 Mar 8	11259059
Factitious hypertension by pseudoephedrine.	2001 Mar-Apr	11239129
Extra-strong graduated compression stocking reduces usage of vasopressor agents during spinal anesthesia for cesarean section.	2001 May	11409475
Direct resolution of (+/-)-ephedrine and atropine into their enantiomers by impregnated TLC.	2001 May	11391670
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man.	2001 May	11381283
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.	2001 May	11361053
Seizure activity and unresponsiveness after hydroxycut ingestion.	2001 May	11349754
Pharmacologic options available to treat symptomatic intradialytic hypotension.	2001 Oct	11602458
High performance liquid chromatography with UV detection for the simultaneous determination of sympathomimetic amines using 4-(4,5-diphenyl-1H-imidazole-2-yl)benzoyl chloride as a label.	2001 Oct	11559922
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations.	2001 Sep	11593992
What constitutes an effective but safe initial dose of lidocaine to test a thoracic epidural catheter?	2001 Sep	11524351
Studying the neuronal side of the synaptic cleft. A tool for investigating the paradox of sympathetic nervous system and heart failure in dilated cardiomyopathy.	2001 Sep	11492981
Rapid chiral on-chip separation with simplified amperometric detection.	2001 Sep 14	11587341
[Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit].	2001 Sep 24	11590951

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosages for the treatment of clinically important hypotension in the setting of anesthesia is an initial dose of 5 to 10 mg administered by intravenous bolus. Administer additional boluses as needed, not to exceed a total dosage of 50 mg.

Route of Administration: Intravenous

In Vitro Use Guide

Segments of guinea-pig ileum were treated with 10(-6)-10(-3) M ephedrine. Ephedrine inhibited the ileal responses to transmural stimulation in the terminal and the proximal ileum with EC50 values of 57.2 and 85.5 uM, respectively. In the proximal part of the ileum, more than 70% of preparations were relaxed by ephedrine.

Name

Type

Language

Ephedrine

Common Name

English

(R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL [WHO-IP]

Systematic Name

English

EPHEDRINE, ANHYDROUS [WHO-IP]

Common Name

English

EPHEDRINE [USP MONOGRAPH]

Common Name

English

EPHEDRINE [VANDF]

Common Name

English

EPHEDRINE [EP MONOGRAPH]

Common Name

English

PSEUDOEPHEDRINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]

Common Name

English

EPHEDRINE [MI]

Common Name

English

NSC-170951

Code

English

(1R,2S)-2-METHYLAMINO-1-PHENYLPROPAN-1-OL

Systematic Name

English

EPHEDRINUM, ANHYDROUS [WHO-IP LATIN]

Common Name

English

NSC-8971

Code

English

EPHEDRINE [MART.]

Common Name

English

XENADRINE

Common Name

English

L-ERYTHRO-2-(METHYLAMINO)-1-PHENYLPROPAN-1-OL

Common Name

English

BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (R-(R*,S*))-

Common Name

English

L-EPHEDRINE

Common Name

English

(-)-EPHEDRINE

Common Name

English

EPHEDRINE [HSDB]

Common Name

English

Ephedrine [WHO-DD]

Common Name

English

EPHEDRINE, ANHYDROUS

Common Name

English

Classification Tree Code System Code

WHO-ATC

S01FB02