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
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
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 Date2016 |
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 |
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Olanzapine-induced urinary incontinence: treatment with ephedrine. | 2000 Aug |
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Caffeine and exercise: metabolism, endurance and performance. | 2001 |
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Effects of two atypical neuroleptics, olanzapine and risperidone, on the function of the urinary bladder and the external urethral sphincter in anesthetized rats. | 2001 |
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Prevention of generalized reactions to contrast media: a consensus report and guidelines. | 2001 |
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Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures. | 2001 Apr |
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The effects of an increase of central blood volume before spinal anesthesia for cesarean delivery: a qualitative systematic review. | 2001 Apr |
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Mass spectrometric quantitation of chiral drugs by the kinetic method. | 2001 Apr 15 |
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Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions. | 2001 Apr 15 |
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Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort. | 2001 Aug |
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Role of the atrial natriuretic factor in obstetric spinal hypotension. | 2001 Aug |
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Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section. | 2001 Aug |
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Hypokalemic metabolic acidosis attributed to cough mixture abuse. | 2001 Aug |
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Continuous production of (R)-phenylacetylcarbinol in an enzyme-membrane reactor using a potent mutant of pyruvate decarboxylase from Zymomonas mobilis. | 2001 Aug 20 |
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Use of nonprescription weight loss products: results from a multistate survey. | 2001 Aug 22-29 |
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Successful management of venous air embolism with inotropic support. | 2001 Feb |
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[Cerebral infarction in a patient consuming MaHuang extract and guarana]. | 2001 Feb 3 |
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[Refractory hypotension sustained during general anesthesia due to chronic treatment with angiotensin-converting enzyme inhibitors]. | 2001 Jan |
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Should the angiotensin II antagonists be discontinued before surgery? | 2001 Jan |
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Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. | 2001 Jan |
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Pre-filled ephedrine syringes. | 2001 Jul |
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The olfactory G protein G(alphaolf) possesses a lower GDP-affinity and deactivates more rapidly than G(salphashort): consequences for receptor-coupling and adenylyl cyclase activation. | 2001 Jul |
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A stable gas chromatography-mass spectrometry analysis system to characterize Ma Huang products found in health foods and supplements. | 2001 Jul |
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Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations. | 2001 Jun |
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Reduced myocardial carbon-11 hydroxyephedrine retention is associated with poor prognosis in chronic heart failure. | 2001 Mar |
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[A case of pulmonary embolism associated with pneumatic tourniquet deflation]. | 2001 Mar |
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Phenylpropanolamine and stroke: the study, the FDA ruling, the implications. | 2001 Mar |
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Ergogenic aids: counseling the athlete. | 2001 Mar 1 |
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Over-the-counter drug use in gymnasiums: an underrecognized substance abuse problem? | 2001 May-Jun |
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Pharmacologic options available to treat symptomatic intradialytic hypotension. | 2001 Oct |
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Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations. | 2001 Sep |
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Phenylephrine added to prophylactic ephedrine infusion during spinal anesthesia for elective cesarean section. | 2001 Sep |
|
Treatment of erectile dysfunction with sildenafil citrate (Viagra) in parkinsonism due to Parkinson's disease or multiple system atrophy with observations on orthostatic hypotension. | 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 |
|
New imaging techniques for cardiovascular autonomic neuropathy: a window on the heart. | 2001 Spring |
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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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
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DEA NO. |
8113
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CFR |
21 CFR 341.16
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WHO-ATC |
A08AA56
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CFR |
21 CFR 1314.20
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WHO-VATC |
QR03CA02
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WHO-ATC |
R01AB05
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WHO-VATC |
QR01AB05
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170951
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SUB13683MIG
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DB01364
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1024
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100000088883
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3072
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D004809
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9294
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EPHEDRINE
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8971
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SUB11936MIG
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GN83C131XS
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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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EPHEDRINE
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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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GN83C131XS
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3966
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556
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DTXSID0022985
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CHEMBL211456
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15407
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ACTIVE MOIETY
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