Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H16O4.C10H15NO |
Molecular Weight | 365.4638 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CC2(C)[C@H](CC[C@@]2(C)C(O)=O)C(O)=O
InChI
InChIKey=PULXXQBPAAYUBD-LGLFLMIDSA-N
InChI=1S/C10H15NO.C10H16O4/c1-8(11-2)10(12)9-6-4-3-5-7-9;1-9(2)6(7(11)12)4-5-10(9,3)8(13)14/h3-8,10-12H,1-2H3;6H,4-5H2,1-3H3,(H,11,12)(H,13,14)/t8-,10-;6-,10+/m01/s1
Molecular Formula | C10H16O4 |
Molecular Weight | 200.2316 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C10H15NO |
Molecular Weight | 165.2322 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|
Guaifenesin- and ephedrine-induced stones. | 1999 Nov |
|
Pharmaceutical cost savings of treating obesity with weight loss medications. | 1999 Nov |
|
The haemodynamic effects of propofol in combination with ephedrine in elderly patients (ASA groups 3 and 4). | 1999 Oct |
|
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 |
|
An evaluation of l-ephedrine neurotoxicity with respect to hyperthermia and caudate/putamen microdialysate levels of ephedrine, dopamine, serotonin, and glutamate. | 2000 May |
|
The effects of ginseng, ephedrine, and caffeine on cognitive performance, mood and energy. | 2001 Apr |
|
[Misuse of drugs in recreational sports]. | 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 |
|
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 |
|
Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort. | 2001 Aug |
|
Role of the atrial natriuretic factor in obstetric spinal hypotension. | 2001 Aug |
|
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section. | 2001 Aug |
|
Prevention and management of hypotension during spinal anaesthesia for elective Caesarean section: a survey of practice. | 2001 Aug |
|
Effect of caffeine and ephedrine ingestion on anaerobic exercise performance. | 2001 Aug |
|
Asymmetric synthesis of chiral organofluorine compounds: use of nonracemic fluoroiodoacetic acid as a practical electrophile and its application to the synthesis of monofluoro hydroxyethylene dipeptide isosteres within a novel series of HIV protease inhibitors. | 2001 Aug 1 |
|
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 |
|
Successful management of venous air embolism with inotropic support. | 2001 Feb |
|
Natural hazards. Tonic or toxic? Americans are gobbling up nature's remedies for everything from obesity to depression. | 2001 Feb 12 |
|
[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 |
|
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 |
|
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training. | 2001 Jul |
|
New observations on the secondary chemistry of world Ephedra (Ephedraceae). | 2001 Jul |
|
Perioperative bradycardia and asystole: relationship to vasovagal syncope and the Bezold-Jarisch reflex. | 2001 Jun |
|
Hypotension in spinal anesthesia for cesarean section: a comparison of 0.5% hyperbaric bupivacaine and 5% hyperbaric lidocaine. | 2001 Jun |
|
Cold-syrup induced movement disorder. | 2001 Jun |
|
It's a rave new world: rave culture and illicit drug use in the young. | 2001 Jun |
|
[A case of pulmonary embolism associated with pneumatic tourniquet deflation]. | 2001 Mar |
|
Phenylpropanolamine and stroke: the study, the FDA ruling, the implications. | 2001 Mar |
|
Comparative oral and topical decongestant effects of phenylpropanolamine and d-pseudoephedrine. | 2001 Mar-Apr |
|
Factitious hypertension by pseudoephedrine. | 2001 Mar-Apr |
|
Extra-strong graduated compression stocking reduces usage of vasopressor agents during spinal anesthesia for cesarean section. | 2001 May |
|
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 |
|
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 |
|
Neuropeptide Y in obese women during treatment with adrenergic modulation drugs. | 2001 May-Jun |
|
Over-the-counter drug use in gymnasiums: an underrecognized substance abuse problem? | 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 |
|
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 |
|
Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations. | 2001 Sep |
|
[Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit]. | 2001 Sep 24 |
|
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes. | 2001 Sep 5 |
|
Effect of sympathetic reinnervation on cardiac performance after heart transplantation. | 2001 Sep 6 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:09:30 GMT 2023
by
admin
on
Fri Dec 15 15:09:30 GMT 2023
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Record UNII |
W56S9O8P5Y
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Record Status |
Validated (UNII)
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Record Version |
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17140-28-2
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DTXSID40169084
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71587013
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ACTIVE MOIETY |