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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 of EPHEDRINE TARTRATE

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P07550|||Q53GA6|||Q9UCZ3
Gene ID: 154.0
Gene Symbol: ADRB2
Target Organism: Homo sapiens (Human)
0.36 µM [EC50]
4.95 null [pKi]
Target ID: P08588
Gene ID: 153.0
Gene Symbol: ADRB1
Target Organism: Homo sapiens (Human)
0.5 µM [EC50]
4.83 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
79.4 ng/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.75 h
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
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
PubMed

PubMed

TitleDatePubMed
Caffeine and exercise: metabolism, endurance and performance.
2001
Prevention of generalized reactions to contrast media: a consensus report and guidelines.
2001
Recurrent ischaemic colitis associated with pseudoephedrine use.
2001 Apr
[Misuse of drugs in recreational sports].
2001 Apr
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001 Apr
The many faces of ecstasy.
2001 Apr
The effects of an increase of central blood volume before spinal anesthesia for cesarean delivery: a qualitative systematic review.
2001 Apr
Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions.
2001 Apr 15
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
Dietary supplements containing ephedra alkaloids.
2001 Apr 5
Dietary supplements containing ephedra alkaloids.
2001 Apr 5
Phenylpropanolamine and hemorrhagic stroke.
2001 Apr 5
Ondansetron versus dehydrobenzoperidol and metoclopramide for management of postoperative nausea in laparoscopic surgery patients.
2001 Apr-Jun
Role of the atrial natriuretic factor in obstetric spinal hypotension.
2001 Aug
Dose of prophylactic intravenous ephedrine during spinal anesthesia for cesarean section.
2001 Aug
Prevention and management of hypotension during spinal anaesthesia for elective Caesarean section: a survey of practice.
2001 Aug
Hypokalemic metabolic acidosis attributed to cough mixture abuse.
2001 Aug
Asymmetric synthesis of chiral organofluorine compounds: use of nonracemic fluoroiodoacetic acid as a practical electrophile and its application to the synthesis of monofluoro hydroxyethylene dipeptide isosteres within a novel series of HIV protease inhibitors.
2001 Aug 1
Application of carboxymethyl-beta-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters.
2001 Aug 17
Continuous production of (R)-phenylacetylcarbinol in an enzyme-membrane reactor using a potent mutant of pyruvate decarboxylase from Zymomonas mobilis.
2001 Aug 20
Use of nonprescription weight loss products: results from a multistate survey.
2001 Aug 22-29
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training.
2001 Jul
Pre-filled ephedrine syringes.
2001 Jul
New observations on the secondary chemistry of world Ephedra (Ephedraceae).
2001 Jul
Determination of ephedrines in urine by gas chromatography-mass spectrometry.
2001 Jul 15
Perioperative bradycardia and asystole: relationship to vasovagal syncope and the Bezold-Jarisch reflex.
2001 Jun
Nutritional supplements as a source for positive doping cases?
2001 Jun
Reduced myocardial carbon-11 hydroxyephedrine retention is associated with poor prognosis in chronic heart failure.
2001 Mar
[A case of pulmonary embolism associated with pneumatic tourniquet deflation].
2001 Mar
Venlafaxine occupation at the noradrenaline reuptake site: in-vivo determination in healthy volunteers.
2001 Mar
High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities.
2001 Mar
Phenylpropanolamine and stroke: the study, the FDA ruling, the implications.
2001 Mar
Ergogenic aids: counseling the athlete.
2001 Mar 1
[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus].
2001 Mar 20
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
Extra-strong graduated compression stocking reduces usage of vasopressor agents during spinal anesthesia for cesarean section.
2001 May
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man.
2001 May
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.
2001 May
Determination of ephedrine-type alkaloids in dietary supplements by LC/MS using a stable-isotope labeled internal standard.
2001 May-Jun
Over-the-counter drug use in gymnasiums: an underrecognized substance abuse problem?
2001 May-Jun
The anesthetic management of triplet cesarean delivery: a retrospective case series of maternal outcomes.
2001 Oct
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
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations.
2001 Sep
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry.
2001 Sep
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
Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations.
2001 Sep
Rapid chiral on-chip separation with simplified amperometric detection.
2001 Sep 14
[Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit].
2001 Sep 24
A history of nebulization.
2001 Spring
New imaging techniques for cardiovascular autonomic neuropathy: a window on the heart.
2001 Spring
Patents

Sample Use Guides

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 GMT 2023
Edited
by admin
on Sat Dec 16 11:18:44 GMT 2023
Record UNII
WT9D3J0JEU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPHEDRINE TARTRATE
WHO-DD  
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
Created by admin on Sat Dec 16 11:18:44 GMT 2023 , Edited by admin on Sat Dec 16 11:18:44 GMT 2023
PRIMARY
CAS
51442-15-0
Created by admin on Sat Dec 16 11:18:44 GMT 2023 , Edited by admin on Sat Dec 16 11:18:44 GMT 2023
PRIMARY
EVMPD
SUB13689MIG
Created by admin on Sat Dec 16 11:18:44 GMT 2023 , Edited by admin on Sat Dec 16 11:18:44 GMT 2023
PRIMARY
FDA UNII
WT9D3J0JEU
Created by admin on Sat Dec 16 11:18:44 GMT 2023 , Edited by admin on Sat Dec 16 11:18:44 GMT 2023
PRIMARY
PUBCHEM
91936865
Created by admin on Sat Dec 16 11:18:44 GMT 2023 , Edited by admin on Sat Dec 16 11:18:44 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY