EPHEDRINE TARTRATE

US Approved OTC

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H15NO.C4H6O6
Molecular Weight	315.319
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=JEVMMZKFIBRWHJ-UOUHESHZSA-N

InChI=1S/C10H15NO.C4H6O6/c1-8(11-2)10(12)9-6-4-3-5-7-9;5-1(3(7)8)2(6)4(9)10/h3-8,10-12H,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t8-,10-;1-,2-/m01/s1

HIDE SMILES / InChI

Molecular Formula	C10H15NO
Molecular Weight	165.2322
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 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
l-Ephedrine is a major constituent of Mao-Bushi-Saishin-To, one of the formulas of Chinese medicine, which shows immediate inhibition after oral administration of passive cutaneous anaphylaxis in rats.	2000 Aug	11028756
An evaluation of l-ephedrine neurotoxicity with respect to hyperthermia and caudate/putamen microdialysate levels of ephedrine, dopamine, serotonin, and glutamate.	2000 May	10788568
Caffeine and exercise: metabolism, endurance and performance.	2001	11583104
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
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
Mass spectrometric quantitation of chiral drugs by the kinetic method.	2001 Apr 15	11338581
Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions.	2001 Apr 15	11338580
Dietary supplements containing ephedra alkaloids.	2001 Apr 5	11291669
Dietary supplements containing ephedra alkaloids.	2001 Apr 5	11291668
Ondansetron versus dehydrobenzoperidol and metoclopramide for management of postoperative nausea in laparoscopic surgery patients.	2001 Apr-Jun	11394426
Dose of prophylactic intravenous ephedrine during spinal anesthesia for cesarean section.	2001 Aug	11498318
Effect of caffeine and ephedrine ingestion on anaerobic exercise performance.	2001 Aug	11474345
The trouble with fat-burner pills.	2001 Aug 27	11534484
Ephedra is linked to CNS, cardiovascular risks.	2001 Feb	11249416
Natural hazards. Tonic or toxic? Americans are gobbling up nature's remedies for everything from obesity to depression.	2001 Feb 12	11216231
[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
[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
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.	2001 Jan	11071707
Suspected caffeine and ephedrine toxicosis resulting from ingestion of an herbal supplement containing guarana and ma huang in dogs: 47 cases (1997-1999).	2001 Jan 15	11195828
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
Perioperative bradycardia and asystole: relationship to vasovagal syncope and the Bezold-Jarisch reflex.	2001 Jun	11573596
It's a rave new world: rave culture and illicit drug use in the young.	2001 Jun	11405616
Nutritional supplements as a source for positive doping cases?	2001 Jun	11402257
Reduced myocardial carbon-11 hydroxyephedrine retention is associated with poor prognosis in chronic heart failure.	2001 Mar	11315607
[A case of pulmonary embolism associated with pneumatic tourniquet deflation].	2001 Mar	11296445
Venlafaxine occupation at the noradrenaline reuptake site: in-vivo determination in healthy volunteers.	2001 Mar	11277612
High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities.	2001 Mar	11277256
[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus].	2001 Mar 20	11332378
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
Fulminant exacerbation of autoimmune hepatitis after the use of ma huang.	2001 May	11374728
Neuropeptide Y in obese women during treatment with adrenergic modulation drugs.	2001 May-Jun	11386016
The anesthetic management of triplet cesarean delivery: a retrospective case series of maternal outcomes.	2001 Oct	11574371
Phenylephrine added to prophylactic ephedrine infusion during spinal anesthesia for elective cesarean section.	2001 Sep	11575540
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry.	2001 Sep	11565946
Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations.	2001 Sep	11470203
[Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit].	2001 Sep 24	11590951
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:18:44 UTC 2023` Edited by `admin` on `Sat Dec 16 11:18:44 UTC 2023`
Record UNII	WT9D3J0JEU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPHEDRINE TARTRATE

Common Name

English

BENZENEMETHANOL, .ALPHA.-((1S)-1-(METHYLAMINO)ETHYL)-, (.ALPHA.R)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT)

Systematic Name

English

Ephedrine tartrate [WHO-DD]

Common Name

English

Code System Code Type Description

SMS_ID

100000078947