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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 C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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

1.46188796E12
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
Guaifenesin- and ephedrine-induced stones.
1999 Nov
Olanzapine-induced urinary incontinence: treatment with ephedrine.
2000 Aug
An evaluation of l-ephedrine neurotoxicity with respect to hyperthermia and caudate/putamen microdialysate levels of ephedrine, dopamine, serotonin, and glutamate.
2000 May
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
Mass spectrometric quantitation of chiral drugs by the kinetic method.
2001 Apr 15
Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions.
2001 Apr 15
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
Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort.
2001 Aug
Prevention and management of hypotension during spinal anaesthesia for elective Caesarean section: a survey of practice.
2001 Aug
Effect of caffeine and ephedrine ingestion on anaerobic exercise performance.
2001 Aug
Application of carboxymethyl-beta-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters.
2001 Aug 17
Ephedra is linked to CNS, cardiovascular risks.
2001 Feb
Natural hazards. Tonic or toxic? Americans are gobbling up nature's remedies for everything from obesity to depression.
2001 Feb 12
[Cerebral infarction in a patient consuming MaHuang extract and guarana].
2001 Feb 3
[Refractory hypotension sustained during general anesthesia due to chronic treatment with angiotensin-converting enzyme inhibitors].
2001 Jan
NCAA study of substance use and abuse habits of college student-athletes.
2001 Jan
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
Determination of ephedrines in urine by gas chromatography-mass spectrometry.
2001 Jul 15
Spinal anaesthesia for Caesarean section with bupivacaine 5 mg ml(-1) in glucose 8 or 80 mg ml(-1).
2001 Jun
Hypotension in spinal anesthesia for cesarean section: a comparison of 0.5% hyperbaric bupivacaine and 5% hyperbaric lidocaine.
2001 Jun
Evaluation of pre-emptive intramuscular phenylephrine and ephedrine for reduction of spinal anaesthesia-induced hypotension during Caesarean section.
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
Induction with propofol target-concentration infusion vs. 8% sevoflurane inhalation and alfentanil in hypertensive patients.
2001 Mar
Ergogenic aids: counseling the athlete.
2001 Mar 1
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
Factitious hypertension by pseudoephedrine.
2001 Mar-Apr
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man.
2001 May
Fulminant exacerbation of autoimmune hepatitis after the use of ma huang.
2001 May
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.
2001 May
Neuropeptide Y in obese women during treatment with adrenergic modulation drugs.
2001 May-Jun
Pharmacologic options available to treat symptomatic intradialytic hypotension.
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
What constitutes an effective but safe initial dose of lidocaine to test a thoracic epidural catheter?
2001 Sep
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
Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations.
2001 Sep
[Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit].
2001 Sep 24
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes.
2001 Sep 5
Effect of sympathetic reinnervation on cardiac performance after heart transplantation.
2001 Sep 6
A history of nebulization.
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 Thu Jul 06 16:54:45 UTC 2023
Edited
by admin
on Thu Jul 06 16:54:45 UTC 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 Thu Jul 06 16:54:45 UTC 2023 , Edited by admin on Thu Jul 06 16:54:45 UTC 2023
PRIMARY
CAS
51442-15-0
Created by admin on Thu Jul 06 16:54:45 UTC 2023 , Edited by admin on Thu Jul 06 16:54:45 UTC 2023
PRIMARY
EVMPD
SUB13689MIG
Created by admin on Thu Jul 06 16:54:45 UTC 2023 , Edited by admin on Thu Jul 06 16:54:45 UTC 2023
PRIMARY
FDA UNII
WT9D3J0JEU
Created by admin on Thu Jul 06 16:54:45 UTC 2023 , Edited by admin on Thu Jul 06 16:54:45 UTC 2023
PRIMARY
PUBCHEM
91936865
Created by admin on Thu Jul 06 16:54:45 UTC 2023 , Edited by admin on Thu Jul 06 16:54:45 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY