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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15NO.ClH
Molecular Weight 201.693
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Ephedrine hydrochloride

SMILES

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

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 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H15NO
Molecular Weight 165.2322
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

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
The haemodynamic effects of propofol in combination with ephedrine in elderly patients (ASA groups 3 and 4).
1999 Oct
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
Minidose bupivacaine-fentanyl spinal anesthesia for surgical repair of hip fracture in the aged.
2000 Jan
Caffeine and exercise: metabolism, endurance and performance.
2001
Effects of two atypical neuroleptics, olanzapine and risperidone, on the function of the urinary bladder and the external urethral sphincter in anesthetized rats.
2001
Prevention of generalized reactions to contrast media: a consensus report and guidelines.
2001
Recurrent ischaemic colitis associated with pseudoephedrine use.
2001 Apr
Stimulatory effect of D-ephedrine on beta3-adrenoceptors in adipose tissue of rats.
2001 Apr 12
Dietary supplements containing ephedra alkaloids.
2001 Apr 5
Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort.
2001 Aug
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section.
2001 Aug
Hypokalemic metabolic acidosis attributed to cough mixture abuse.
2001 Aug
Application of carboxymethyl-beta-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters.
2001 Aug 17
The trouble with fat-burner pills.
2001 Aug 27
Ephedra is linked to CNS, cardiovascular risks.
2001 Feb
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.
2001 Jan
NCAA study of substance use and abuse habits of college student-athletes.
2001 Jan
Should the angiotensin II antagonists be discontinued before surgery?
2001 Jan
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training.
2001 Jul
A stable gas chromatography-mass spectrometry analysis system to characterize Ma Huang products found in health foods and supplements.
2001 Jul
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
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
[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
Comparative oral and topical decongestant effects of phenylpropanolamine and d-pseudoephedrine.
2001 Mar-Apr
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.
2001 May
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
Phenylephrine added to prophylactic ephedrine infusion during spinal anesthesia for elective cesarean section.
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
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
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
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 Dec 15 16:38:04 GMT 2023
Edited
by admin
on Fri Dec 15 16:38:04 GMT 2023
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 [VANDF]
Common Name English
L-EPHEDRINE HYDROCHLORIDE
Common Name English
EPHEDRINE HYDROCHLORIDE [JAN]
Common Name English
EPHEDRINE HYDROCHLORIDE [WHO-IP]
Common Name English
(R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL HYDROCHLORIDE [WHO-IP]
Systematic Name English
EPHEDRINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, HYDROCHLORIDE, (R-(R*,S*))-
Common Name English
REZIPRES
Brand Name English
EPHEDRINE HYDROCHLORIDE [MI]
Common Name English
EPHEDRINE HYDROCHLORIDE [EP IMPURITY]
Common Name English
EPHEDRINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
NSC-759611
Code English
EPHEDRINE HYDROCHLORIDE [USP-RS]
Common Name English
EPHEDRINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
(-)-EPHEDRINE HYDROCHLORIDE [WHO-IP]
Common Name English
EPHEDRINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
(-)-EPHEDRINE HYDROCHLORIDE
WHO-IP  
Common Name English
Ephedrine hydrochloride [WHO-DD]
Common Name English
EPHEDRINE HCL
Common Name English
Classification Tree Code System Code
CFR 21 CFR 341.20
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
CFR 21 CFR 341.16
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
CFR 21 CFR 349.18
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
Code System Code Type Description
CAS
50-98-6
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
MERCK INDEX
m4933
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
200-074-6
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
ChEMBL
CHEMBL211456
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
EVMPD
SUB13686MIG
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
FDA UNII
NLJ6390P1Z
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
DAILYMED
NLJ6390P1Z
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
PUBCHEM
65326
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
RXCUI
91165
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY RxNorm
NSC
759611
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
NCI_THESAURUS
C75031
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
RS_ITEM_NUM
1235999
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID1045825
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EPHEDRINE HYDROCHLORIDE
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
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 Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
SMS_ID
100000091342
Created by admin on Fri Dec 15 16:38:04 GMT 2023 , Edited by admin on Fri Dec 15 16:38:04 GMT 2023
PRIMARY
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BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
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