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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15NO
Molecular Weight 165.2326
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPHEDRINE

SMILES

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

InChI

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

HIDE SMILES / InChI
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
The use of oral vasopressors in the management of autonomic dysfunction and orthostatic hypotension.
1999 May
Pharmaceutical cost savings of treating obesity with weight loss medications.
1999 Nov
Recurrent ischaemic colitis associated with pseudoephedrine use.
2001 Apr
The effects of ginseng, ephedrine, and caffeine on cognitive performance, mood and energy.
2001 Apr
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001 Apr
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
Phenylpropanolamine and hemorrhagic stroke.
2001 Apr 5
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section.
2001 Aug
Continuous production of (R)-phenylacetylcarbinol in an enzyme-membrane reactor using a potent mutant of pyruvate decarboxylase from Zymomonas mobilis.
2001 Aug 20
The trouble with fat-burner pills.
2001 Aug 27
[Cerebral infarction in a patient consuming MaHuang extract and guarana].
2001 Feb 3
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
Suspected caffeine and ephedrine toxicosis resulting from ingestion of an herbal supplement containing guarana and ma huang in dogs: 47 cases (1997-1999).
2001 Jan 15
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
Determination of ephedrines in urine by gas chromatography-mass spectrometry.
2001 Jul 15
Hypotension in spinal anesthesia for cesarean section: a comparison of 0.5% hyperbaric bupivacaine and 5% hyperbaric lidocaine.
2001 Jun
Nutritional supplements as a source for positive doping cases?
2001 Jun
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations.
2001 Jun
Reduced myocardial carbon-11 hydroxyephedrine retention is associated with poor prognosis in chronic heart failure.
2001 Mar
Phenylpropanolamine and stroke: the study, the FDA ruling, the implications.
2001 Mar
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
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
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
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
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.
Name Type Language
EPHEDRINE
HSDB   MART.   MI   USP   VANDF   WHO-DD  
Common Name English
(R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL [WHO-IP]
Systematic Name English
EPHEDRINE [WHO-DD]
Common Name English
EPHEDRINE, ANHYDROUS [WHO-IP]
Common Name English
EPHEDRINE [VANDF]
Common Name English
EPHEDRINE [EP MONOGRAPH]
Common Name English
EPHEDRINE [MI]
Common Name English
PSEUDOEPHEDRINE HYDROCHLORIDE SPECIFIED IMPURITY A [EP]
Common Name English
EPHEDRINE [USP]
Common Name English
NSC-170951
Code English
(1R,2S)-2-METHYLAMINO-1-PHENYLPROPAN-1-OL
Systematic Name English
EPHEDRINUM, ANHYDROUS [WHO-IP LATIN]
Common Name English
NSC-8971
Code English
EPHEDRINE [MART.]
Common Name English
XENADRINE
Common Name English
L-ERYTHRO-2-(METHYLAMINO)-1-PHENYLPROPAN-1-OL
Common Name English
BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (R-(R*,S*))-
Common Name English
EPHEDRINE, ANHYDROUS [EP]
Common Name English
L-EPHEDRINE
Common Name English
(-)-EPHEDRINE
Common Name English
EPHEDRINE [HSDB]
Common Name English
EPHEDRINE, ANHYDROUS
EP   WHO-IP  
Common Name English
Classification Tree Code System Code
WHO-ATC S01FB02
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-ATC R01AA03
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-VATC QC01CA26
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-ATC R03CA02
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
NDF-RT N0000175552
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 1.2
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
CFR 21 CFR 119.1
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-VATC QR01AA03
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
CFR 21 CFR 1315.13
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-ATC C01CA26
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-VATC QS01FB02
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
CFR 21 CFR 341.20
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
NCI_THESAURUS C87053
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
NDF-RT N0000175555
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-VATC QG04BX90
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
NDF-RT N0000192563
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
CFR 21 CFR 341.16
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-ATC A08AA56
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
CFR 21 CFR 1314.20
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-VATC QR03CA02
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-ATC R01AB05
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
WHO-VATC QR01AB05
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
Code System Code Type Description
EVMPD
SUB13683MIG
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
DRUG BANK
DB01364
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
DRUG CENTRAL
1024
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
HSDB
3072
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
MESH
D004809
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-080-5
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
PUBCHEM
9294
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
WIKIPEDIA
EPHEDRINE
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
EVMPD
SUB11936MIG
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
FDA UNII
GN83C131XS
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
NCI_THESAURUS
C472
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
MERCK INDEX
M4933
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY Merck Index
CAS
299-42-3
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EPHEDRINE
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
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.
RXCUI
3966
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY RxNorm
IUPHAR
556
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
EPA CompTox
299-42-3
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY
ChEMBL
CHEMBL211456
Created by admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
PRIMARY