U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15NO.ClH
Molecular Weight 201.6935
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPHEDRINE HYDROCHLORIDE

SMILES

C[C@@]([H])([C@@]([H])(c1ccccc1)O)NC.Cl

InChI

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H15NO
Molecular Weight 165.2326
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
Effects of two atypical neuroleptics, olanzapine and risperidone, on the function of the urinary bladder and the external urethral sphincter in anesthetized rats.
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
Stimulatory effect of D-ephedrine on beta3-adrenoceptors in adipose tissue of rats.
2001 Apr 12
Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions.
2001 Apr 15
Dietary supplements containing ephedra alkaloids.
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
Role of the atrial natriuretic factor in obstetric spinal hypotension.
2001 Aug
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section.
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
Effect of caffeine and ephedrine ingestion on anaerobic exercise performance.
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 trouble with fat-burner pills.
2001 Aug 27
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.
2001 Jan
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training.
2001 Jul
Pre-filled ephedrine syringes.
2001 Jul
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
A stable gas chromatography-mass spectrometry analysis system to characterize Ma Huang products found in health foods and supplements.
2001 Jul
Perioperative bradycardia and asystole: relationship to vasovagal syncope and the Bezold-Jarisch reflex.
2001 Jun
Hypotension in spinal anesthesia for cesarean section: a comparison of 0.5% hyperbaric bupivacaine and 5% hyperbaric lidocaine.
2001 Jun
Cold-syrup induced movement disorder.
2001 Jun
It's a rave new world: rave culture and illicit drug use in the young.
2001 Jun
Evaluation of pre-emptive intramuscular phenylephrine and ephedrine for reduction of spinal anaesthesia-induced hypotension during Caesarean section.
2001 Mar
Reduced myocardial carbon-11 hydroxyephedrine retention is associated with poor prognosis in chronic heart failure.
2001 Mar
Venlafaxine occupation at the noradrenaline reuptake site: in-vivo determination in healthy volunteers.
2001 Mar
[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus].
2001 Mar 20
Comparative oral and topical decongestant effects of phenylpropanolamine and d-pseudoephedrine.
2001 Mar-Apr
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
Fulminant exacerbation of autoimmune hepatitis after the use of ma huang.
2001 May
Seizure activity and unresponsiveness after hydroxycut ingestion.
2001 May
Determination of ephedrine-type alkaloids in dietary supplements by LC/MS using a stable-isotope labeled internal standard.
2001 May-Jun
Neuropeptide Y in obese women during treatment with adrenergic modulation drugs.
2001 May-Jun
Over-the-counter drug use in gymnasiums: an underrecognized substance abuse problem?
2001 May-Jun
Pharmacologic options available to treat symptomatic intradialytic hypotension.
2001 Oct
The anesthetic management of triplet cesarean delivery: a retrospective case series of maternal outcomes.
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
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 Fri Jun 25 21:12:47 UTC 2021
Edited
by admin
on Fri Jun 25 21:12:47 UTC 2021
Record UNII
NLJ6390P1Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPHEDRINE HYDROCHLORIDE
EP   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
EPHEDRINE HYDROCHLORIDE [MART.]
Common Name English
EPHEDRINE HYDROCHLORIDE [WHO-DD]
Common Name English
EPHEDRINE HYDROCHLORIDE [VANDF]
Common Name English
L-EPHEDRINE HYDROCHLORIDE
Common Name English
EPHEDRINE HYDROCHLORIDE [WHO-IP]
Common Name English
(R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL HYDROCHLORIDE [WHO-IP]
Systematic Name English
BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, HYDROCHLORIDE, (R-(R*,S*))-
Common Name English
EPHEDRINE HYDROCHLORIDE [MI]
Common Name English
EPHEDRINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
NSC-759611
Code English
EPHEDRINE HYDROCHLORIDE [EP]
Common Name English
EPHEDRINE HYDROCHLORIDE [USP-RS]
Common Name English
EPHEDRINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
EPHEDRINE HYDROCHLORIDE [USP]
Common Name English
(-)-EPHEDRINE HYDROCHLORIDE [WHO-IP]
Common Name English
(-)-EPHEDRINE HYDROCHLORIDE
WHO-IP  
Common Name English
EPHEDRINE HCL
Common Name English
Classification Tree Code System Code
CFR 21 CFR 341.20
Created by admin on Fri Jun 25 21:12:47 UTC 2021 , Edited by admin on Fri Jun 25 21:12:47 UTC 2021
NCI_THESAURUS C29747
Created by admin on Fri Jun 25 21:12:48 UTC 2021 , Edited by admin on Fri Jun 25 21:12:48 UTC 2021
CFR 21 CFR 341.16
Created by admin on Fri Jun 25 21:12:47 UTC 2021 , Edited by admin on Fri Jun 25 21:12:47 UTC 2021
CFR 21 CFR 349.18
Created by admin on Fri Jun 25 21:12:47 UTC 2021 , Edited by admin on Fri Jun 25 21:12:47 UTC 2021
Code System Code Type Description
CAS
50-98-6
Created by admin on Fri Jun 25 21:12:47 UTC 2021 , Edited by admin on Fri Jun 25 21:12:47 UTC 2021
PRIMARY
MERCK INDEX
M4933
Created by admin on Fri Jun 25 21:12:48 UTC 2021 , Edited by admin on Fri Jun 25 21:12:48 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
200-074-6
Created by admin on Fri Jun 25 21:12:47 UTC 2021 , Edited by admin on Fri Jun 25 21:12:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL211456
Created by admin on Fri Jun 25 21:12:47 UTC 2021 , Edited by admin on Fri Jun 25 21:12:47 UTC 2021
PRIMARY
EVMPD
SUB13686MIG
Created by admin on Fri Jun 25 21:12:47 UTC 2021 , Edited by admin on Fri Jun 25 21:12:47 UTC 2021
PRIMARY
FDA UNII
NLJ6390P1Z
Created by admin on Fri Jun 25 21:12:48 UTC 2021 , Edited by admin on Fri Jun 25 21:12:48 UTC 2021
PRIMARY
PUBCHEM
65326
Created by admin on Fri Jun 25 21:12:48 UTC 2021 , Edited by admin on Fri Jun 25 21:12:48 UTC 2021
PRIMARY
RXCUI
91165
Created by admin on Fri Jun 25 21:12:48 UTC 2021 , Edited by admin on Fri Jun 25 21:12:48 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C75031
Created by admin on Fri Jun 25 21:12:48 UTC 2021 , Edited by admin on Fri Jun 25 21:12:48 UTC 2021
PRIMARY
EPA CompTox
50-98-6
Created by admin on Fri Jun 25 21:12:47 UTC 2021 , Edited by admin on Fri Jun 25 21:12:47 UTC 2021
PRIMARY
USP_CATALOG
1235999
Created by admin on Fri Jun 25 21:12:48 UTC 2021 , Edited by admin on Fri Jun 25 21:12:48 UTC 2021
PRIMARY USP-RS
WHO INTERNATIONAL PHARMACOPEIA
EPHEDRINE HYDROCHLORIDE
Created by admin on Fri Jun 25 21:12:48 UTC 2021 , Edited by admin on Fri Jun 25 21:12:48 UTC 2021
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless.Solubility: Soluble in 4 parts of water; soluble in ethanol (~750 g/l) TS; practically insoluble in ether R.Category: Antiasthmatic drug.Storage: Ephedrine hydrochloride should be kept in a well-closed container, protected from light.Additional information: Ephedrine hydrochloride darkens on exposure to light.RequirementsDefinition: Ephedrine hydrochloride contains not less than 99.0% and not more than 101.0% of C10H15NO,HCl, calculated withreference to the dried substance.
DRUG BANK
DBSALT001513
Created by admin on Fri Jun 25 21:12:47 UTC 2021 , Edited by admin on Fri Jun 25 21:12:47 UTC 2021
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY