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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15NO
Molecular Weight 165.2322
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Ephedrine

SMILES

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

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

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
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
Recurrent ischaemic colitis associated with pseudoephedrine use.
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
Dietary supplements containing ephedra alkaloids.
2001 Apr 5
Dietary supplements containing ephedra alkaloids.
2001 Apr 5
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
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
Ephedra is linked to CNS, cardiovascular risks.
2001 Feb
[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
[Refractory hypotension sustained during general anesthesia due to chronic treatment with angiotensin-converting enzyme inhibitors].
2001 Jan
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training.
2001 Jul
Pre-filled ephedrine syringes.
2001 Jul
New observations on the secondary chemistry of world Ephedra (Ephedraceae).
2001 Jul
Determination of ephedrines in urine by gas chromatography-mass spectrometry.
2001 Jul 15
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
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations.
2001 Jun
Evaluation of pre-emptive intramuscular phenylephrine and ephedrine for reduction of spinal anaesthesia-induced hypotension during Caesarean section.
2001 Mar
[A case of pulmonary embolism associated with pneumatic tourniquet deflation].
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
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
[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
Factitious hypertension by pseudoephedrine.
2001 Mar-Apr
Direct resolution of (+/-)-ephedrine and atropine into their enantiomers by impregnated TLC.
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
The anesthetic management of triplet cesarean delivery: a retrospective case series of maternal outcomes.
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
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
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.
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, ANHYDROUS [WHO-IP]
Common Name English
EPHEDRINE [USP MONOGRAPH]
Common Name English
EPHEDRINE [VANDF]
Common Name English
EPHEDRINE [EP MONOGRAPH]
Common Name English
PSEUDOEPHEDRINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
EPHEDRINE [MI]
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
L-EPHEDRINE
Common Name English
(-)-EPHEDRINE
Common Name English
EPHEDRINE [HSDB]
Common Name English
Ephedrine [WHO-DD]
Common Name English
EPHEDRINE, ANHYDROUS
EP   WHO-IP  
Common Name English
Classification Tree Code System Code
WHO-ATC S01FB02
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
WHO-ATC R01AA03
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WHO-VATC QC01CA26
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WHO-ATC R03CA02
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NDF-RT N0000175552
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WHO-ESSENTIAL MEDICINES LIST 1.2
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CFR 21 CFR 119.1
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WHO-VATC QR01AA03
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CFR 21 CFR 1315.13
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WHO-ATC C01CA26
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WHO-VATC QS01FB02
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CFR 21 CFR 341.20
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NCI_THESAURUS C87053
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NDF-RT N0000175555
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WHO-VATC QG04BX90
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NDF-RT N0000192563
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
DEA NO. 8113
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
CFR 21 CFR 341.16
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
WHO-ATC A08AA56
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
CFR 21 CFR 1314.20
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
WHO-VATC QR03CA02
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
WHO-ATC R01AB05
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WHO-VATC QR01AB05
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
Code System Code Type Description
NSC
170951
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
PRIMARY
EVMPD
SUB13683MIG
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
PRIMARY
DRUG BANK
DB01364
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PRIMARY
DRUG CENTRAL
1024
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PRIMARY
SMS_ID
100000088883
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PRIMARY
HSDB
3072
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PRIMARY
MESH
D004809
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-080-5
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PRIMARY
PUBCHEM
9294
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PRIMARY
WIKIPEDIA
EPHEDRINE
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 GMT 2023
PRIMARY
NSC
8971
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PRIMARY
EVMPD
SUB11936MIG
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PRIMARY
FDA UNII
GN83C131XS
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PRIMARY
NCI_THESAURUS
C472
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PRIMARY
MERCK INDEX
m4933
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PRIMARY Merck Index
CAS
299-42-3
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EPHEDRINE
Created by admin on Fri Dec 15 17:21:03 GMT 2023 , Edited by admin on Fri Dec 15 17:21:03 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.
DAILYMED
GN83C131XS
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PRIMARY
RXCUI
3966
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PRIMARY RxNorm
IUPHAR
556
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PRIMARY
EPA CompTox
DTXSID0022985
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PRIMARY
ChEMBL
CHEMBL211456
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PRIMARY
CHEBI
15407
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