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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C10H15NO.H2O
Molecular Weight 348.4797
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPHEDRINE HEMIHYDRATE

SMILES

O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C2=CC=CC=C2

InChI

InChIKey=ZNGSVRYVWHOWLX-KHFUBBAMSA-N
InChI=1S/2C10H15NO.H2O/c2*1-8(11-2)10(12)9-6-4-3-5-7-9;/h2*3-8,10-12H,1-2H3;1H2/t2*8-,10-;/m00./s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
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
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
Caffeine and exercise: metabolism, endurance and performance.
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
Stimulatory effect of D-ephedrine on beta3-adrenoceptors in adipose tissue of rats.
2001 Apr 12
Mass spectrometric quantitation of chiral drugs by the kinetic method.
2001 Apr 15
Dietary supplements containing ephedra alkaloids.
2001 Apr 5
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
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
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
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
Should the angiotensin II antagonists be discontinued before surgery?
2001 Jan
Combined spinal and epidural anesthesia with low doses of intrathecal bupivacaine in women with severe preeclampsia: a preliminary report.
2001 Jan-Feb
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training.
2001 Jul
Perioperative bradycardia and asystole: relationship to vasovagal syncope and the Bezold-Jarisch reflex.
2001 Jun
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
Cold-syrup induced movement disorder.
2001 Jun
Nutritional supplements as a source for positive doping cases?
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
[A case of pulmonary embolism associated with pneumatic tourniquet deflation].
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
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.
2001 May
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
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
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry.
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
Rapid chiral on-chip separation with simplified amperometric detection.
2001 Sep 14
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 Fri Dec 15 18:14:24 GMT 2023
Edited
by admin
on Fri Dec 15 18:14:24 GMT 2023
Record UNII
HH60WD6JQS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPHEDRINE HEMIHYDRATE
EP   WHO-IP  
Common Name English
BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, HYDRATE (2:1), (R-(R*,S*))-
Common Name English
EPHEDRINE HYDRATE
Common Name English
EPHEDRINE HEMIHYDRATE [EP MONOGRAPH]
Common Name English
EPHEDRINE HEMIHYDRATE [WHO-IP]
Common Name English
BENZENEMETHANOL, .ALPHA.-9(1S)-1-(METHYLAMINO)ETHYL)-, HYDRATE (2:1), (.ALPHA.R)-
Common Name English
EPHEDRINE HEMIHYDRATE [USP MONOGRAPH]
Common Name English
(-)-EPHEDRINE HEMIHYDRATE [WHO-IP]
Common Name English
(R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL HEMIHYDRATE [WHO-IP]
Systematic Name English
BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (R-(R*,S*))-, HEMIHYDRATE
Common Name English
EPHEDRINUM HEMIHYDRATE [WHO-IP LATIN]
Common Name English
Code System Code Type Description
PUBCHEM
67242163
Created by admin on Fri Dec 15 18:14:24 GMT 2023 , Edited by admin on Fri Dec 15 18:14:24 GMT 2023
PRIMARY
EVMPD
SUB11934MIG
Created by admin on Fri Dec 15 18:14:24 GMT 2023 , Edited by admin on Fri Dec 15 18:14:24 GMT 2023
PRIMARY
RXCUI
283561
Created by admin on Fri Dec 15 18:14:24 GMT 2023 , Edited by admin on Fri Dec 15 18:14:24 GMT 2023
PRIMARY RxNorm
SMS_ID
100000091960
Created by admin on Fri Dec 15 18:14:24 GMT 2023 , Edited by admin on Fri Dec 15 18:14:24 GMT 2023
PRIMARY
FDA UNII
HH60WD6JQS
Created by admin on Fri Dec 15 18:14:24 GMT 2023 , Edited by admin on Fri Dec 15 18:14:24 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EPHEDRINE HEMIHYDRATE
Created by admin on Fri Dec 15 18:14:24 GMT 2023 , Edited by admin on Fri Dec 15 18:14:24 GMT 2023
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless or with a slight, aromatic odour.Solubility: Soluble in water; very soluble in ethanol (~750 g/l) TS; freely soluble in ether R.Category: Antiasthmatic drug.Storage: Ephedrine should be kept in a well-closed container, protected from light.Labelling: The designation on the container should state whether the substance is the hemihydrate or is in the anhydrous form.Additional information: Solutions of Ephedrine in chloroform R may become turbid, especially when the substance contains morethan 10 mg of water per g. Even in the absence of light, Ephedrine is gradually degraded on exposure to a humid atmosphere,the decomposition being faster at higher temperatures. Anhydrous Ephedrine melts at about 38?C, whereas Ephedrinehemihydrate melts at about 42?C.
CAS
50906-05-3
Created by admin on Fri Dec 15 18:14:24 GMT 2023 , Edited by admin on Fri Dec 15 18:14:24 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Definition: Ephedrine contains not less than 98.5% and not more than 101.0% of C10H15NO, calculated with reference to the anhydrous substance.
ANHYDROUS->SOLVATE