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
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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P07550|||Q53GA6|||Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) |
0.36 µM [EC50] | ||
Target ID: CHEMBL2094251 |
4.95 null [pKi] | ||
Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) |
0.5 µM [EC50] | ||
Target ID: CHEMBL2095158 |
4.83 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AKOVAZ Approved UseAKOVAZ 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 Date1.46188796E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
79.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/ |
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
Title | Date | PubMed |
---|---|---|
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 |
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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 |
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[Cerebral infarction in a patient consuming MaHuang extract and guarana]. | 2001 Feb 3 |
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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 |
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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 |
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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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6111369
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.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
S01FB02
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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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admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
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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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admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
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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
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CFR |
21 CFR 341.16
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admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
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WHO-ATC |
A08AA56
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admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
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CFR |
21 CFR 1314.20
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admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
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WHO-VATC |
QR03CA02
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admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
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WHO-ATC |
R01AB05
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admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
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WHO-VATC |
QR01AB05
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admin on Fri Jun 25 21:07:29 UTC 2021 , Edited by admin on Fri Jun 25 21:07:29 UTC 2021
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Code System | Code | Type | Description | ||
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SUB13683MIG
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DB01364
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1024
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3072
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D004809
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206-080-5
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9294
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PRIMARY | |||
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EPHEDRINE
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PRIMARY | |||
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SUB11936MIG
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GN83C131XS
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PRIMARY | |||
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C472
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M4933
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PRIMARY | Merck Index | ||
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299-42-3
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PRIMARY | |||
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EPHEDRINE
Created by
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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. | ||
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3966
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PRIMARY | RxNorm | ||
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556
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299-42-3
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CHEMBL211456
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ACTIVE MOIETY
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