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 2662	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 2662	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 2662	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 2662	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 8360	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 1.46188796E12

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
Ephedrine-induced complete atrioventricular block with ventricular asystole during rapid concomitant phenytoin infusion: a case report.	1999 Mar	10407528
Effects of two atypical neuroleptics, olanzapine and risperidone, on the function of the urinary bladder and the external urethral sphincter in anesthetized rats.	2001	11580866
Recurrent ischaemic colitis associated with pseudoephedrine use.	2001 Apr	11478350
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
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
Dietary supplements containing ephedra alkaloids.	2001 Apr 5	11291669
Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort.	2001 Aug	11512648
Prevention and management of hypotension during spinal anaesthesia for elective Caesarean section: a survey of practice.	2001 Aug	11493248
Effect of caffeine and ephedrine ingestion on anaerobic exercise performance.	2001 Aug	11474345
Continuous production of (R)-phenylacetylcarbinol in an enzyme-membrane reactor using a potent mutant of pyruvate decarboxylase from Zymomonas mobilis.	2001 Aug 20	11410856
The trouble with fat-burner pills.	2001 Aug 27	11534484
Ephedra is linked to CNS, cardiovascular risks.	2001 Feb	11249416
[Refractory hypotension sustained during general anesthesia due to chronic treatment with angiotensin-converting enzyme inhibitors].	2001 Jan	11234604
NCAA study of substance use and abuse habits of college student-athletes.	2001 Jan	11176146
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 olfactory G protein G(alphaolf) possesses a lower GDP-affinity and deactivates more rapidly than G(salphashort): consequences for receptor-coupling and adenylyl cyclase activation.	2001 Jul	11461968
New observations on the secondary chemistry of world Ephedra (Ephedraceae).	2001 Jul	11454619
Spinal anaesthesia for Caesarean section with bupivacaine 5 mg ml(-1) in glucose 8 or 80 mg ml(-1).	2001 Jun	11573587
It's a rave new world: rave culture and illicit drug use in the young.	2001 Jun	11405616
Ergogenic aids: counseling the athlete.	2001 Mar 1	11261867
Comparative oral and topical decongestant effects of phenylpropanolamine and d-pseudoephedrine.	2001 Mar-Apr	11345158
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man.	2001 May	11381283
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
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry.	2001 Sep	11565946
Treatment of erectile dysfunction with sildenafil citrate (Viagra) in parkinsonism due to Parkinson's disease or multiple system atrophy with observations on orthostatic hypotension.	2001 Sep	11511713
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
Effect of sympathetic reinnervation on cardiac performance after heart transplantation.	2001 Sep 6	11547742
A history of nebulization.	2001 Spring	11495487
New imaging techniques for cardiovascular autonomic neuropathy: a window on the heart.	2001 Spring	11469712

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