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 |
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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 |
---|---|---|
Olanzapine-induced urinary incontinence: treatment with ephedrine. | 2000 Aug |
|
Minidose bupivacaine-fentanyl spinal anesthesia for surgical repair of hip fracture in the aged. | 2000 Jan |
|
Prevention of generalized reactions to contrast media: a consensus report and guidelines. | 2001 |
|
Recurrent ischaemic colitis associated with pseudoephedrine use. | 2001 Apr |
|
[Misuse of drugs in recreational sports]. | 2001 Apr |
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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 |
|
The many faces of ecstasy. | 2001 Apr |
|
Dietary supplements containing ephedra alkaloids. | 2001 Apr 5 |
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Prevention and management of hypotension during spinal anaesthesia for elective Caesarean section: a survey of practice. | 2001 Aug |
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Effect of caffeine and ephedrine ingestion on anaerobic exercise performance. | 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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[Cerebral infarction in a patient consuming MaHuang extract and guarana]. | 2001 Feb 3 |
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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 |
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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 |
|
Cold-syrup induced movement disorder. | 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 |
|
[A case of pulmonary embolism associated with pneumatic tourniquet deflation]. | 2001 Mar |
|
Ergogenic aids: counseling the athlete. | 2001 Mar 1 |
|
[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus]. | 2001 Mar 20 |
|
The anesthetic management of triplet cesarean delivery: a retrospective case series of maternal outcomes. | 2001 Oct |
|
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations. | 2001 Sep |
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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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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206-080-5
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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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