Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H21NO3 |
| Molecular Weight | 263.3321 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN[C@@H](C)[C@H](OC(=O)CCC(C)=O)C1=CC=CC=C1
InChI
InChIKey=SDERVCYTJVOPPI-WFASDCNBSA-N
InChI=1S/C15H21NO3/c1-11(17)9-10-14(18)19-15(12(2)16-3)13-7-5-4-6-8-13/h4-8,12,15-16H,9-10H2,1-3H3/t12-,15-/m0/s1
| Molecular Formula | C15H21NO3 |
| Molecular Weight | 263.3321 |
| 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 |
|---|---|---|
| Pharmacologic options available to treat symptomatic intradialytic hypotension. | 2001-10 |
|
| The anesthetic management of triplet cesarean delivery: a retrospective case series of maternal outcomes. | 2001-10 |
|
| 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. | 2001-10 |
|
| [Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit]. | 2001-09-24 |
|
| Rapid chiral on-chip separation with simplified amperometric detection. | 2001-09-14 |
|
| Effect of sympathetic reinnervation on cardiac performance after heart transplantation. | 2001-09-06 |
|
| Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes. | 2001-09-05 |
|
| Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations. | 2001-09 |
|
| Phenylephrine added to prophylactic ephedrine infusion during spinal anesthesia for elective cesarean section. | 2001-09 |
|
| Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry. | 2001-09 |
|
| What constitutes an effective but safe initial dose of lidocaine to test a thoracic epidural catheter? | 2001-09 |
|
| Treatment of erectile dysfunction with sildenafil citrate (Viagra) in parkinsonism due to Parkinson's disease or multiple system atrophy with observations on orthostatic hypotension. | 2001-09 |
|
| Studying the neuronal side of the synaptic cleft. A tool for investigating the paradox of sympathetic nervous system and heart failure in dilated cardiomyopathy. | 2001-09 |
|
| Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations. | 2001-09 |
|
| Use of nonprescription weight loss products: results from a multistate survey. | 2001-08-31 |
|
| The trouble with fat-burner pills. | 2001-08-27 |
|
| Continuous production of (R)-phenylacetylcarbinol in an enzyme-membrane reactor using a potent mutant of pyruvate decarboxylase from Zymomonas mobilis. | 2001-08-20 |
|
| Application of carboxymethyl-beta-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters. | 2001-08-17 |
|
| 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. | 2001-08-01 |
|
| Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort. | 2001-08 |
|
| Role of the atrial natriuretic factor in obstetric spinal hypotension. | 2001-08 |
|
| Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section. | 2001-08 |
|
| Dose of prophylactic intravenous ephedrine during spinal anesthesia for cesarean section. | 2001-08 |
|
| Prevention and management of hypotension during spinal anaesthesia for elective Caesarean section: a survey of practice. | 2001-08 |
|
| Hypokalemic metabolic acidosis attributed to cough mixture abuse. | 2001-08 |
|
| Effect of caffeine and ephedrine ingestion on anaerobic exercise performance. | 2001-08 |
|
| Determination of ephedrines in urine by gas chromatography-mass spectrometry. | 2001-07-15 |
|
| The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training. | 2001-07 |
|
| Pre-filled ephedrine syringes. | 2001-07 |
|
| 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. | 2001-07 |
|
| A stable gas chromatography-mass spectrometry analysis system to characterize Ma Huang products found in health foods and supplements. | 2001-07 |
|
| New observations on the secondary chemistry of world Ephedra (Ephedraceae). | 2001-07 |
|
| Reappearance of cardiac presynaptic sympathetic nerve terminals in the transplanted heart: correlation between PET using (11)C-hydroxyephedrine and invasively measured norepinephrine release. | 2001-07 |
|
| Determination of ephedrine-type alkaloids in dietary supplements by LC/MS using a stable-isotope labeled internal standard. | 2001-06-22 |
|
| Perioperative bradycardia and asystole: relationship to vasovagal syncope and the Bezold-Jarisch reflex. | 2001-06 |
|
| Spinal anaesthesia for Caesarean section with bupivacaine 5 mg ml(-1) in glucose 8 or 80 mg ml(-1). | 2001-06 |
|
| Hypotension in spinal anesthesia for cesarean section: a comparison of 0.5% hyperbaric bupivacaine and 5% hyperbaric lidocaine. | 2001-06 |
|
| Cold-syrup induced movement disorder. | 2001-06 |
|
| It's a rave new world: rave culture and illicit drug use in the young. | 2001-06 |
|
| Nutritional supplements as a source for positive doping cases? | 2001-06 |
|
| Extra-strong graduated compression stocking reduces usage of vasopressor agents during spinal anesthesia for cesarean section. | 2001-05 |
|
| Stimulatory effect of D-ephedrine on beta3-adrenoceptors in adipose tissue of rats. | 2001-04-12 |
|
| Recurrent ischaemic colitis associated with pseudoephedrine use. | 2001-04 |
|
| Evaluation of pre-emptive intramuscular phenylephrine and ephedrine for reduction of spinal anaesthesia-induced hypotension during Caesarean section. | 2001-03 |
|
| Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients. | 2001-01 |
|
| 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 |
|
| Prevention of generalized reactions to contrast media: a consensus report and guidelines. | 2001 |
|
| A history of nebulization. | 2001 |
|
| New imaging techniques for cardiovascular autonomic neuropathy: a window on the heart. | 2001 |
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
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
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Edited
Mon Mar 31 22:32:36 GMT 2025
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Mon Mar 31 22:32:36 GMT 2025
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| Record UNII |
T9S008S8JL
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| Record Status |
Validated (UNII)
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| Record Version |
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SUB01906MIG
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25021608
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T9S008S8JL
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100000087264
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1082659-36-6
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NON-SPECIFIC STEREOCHEMISTRY |
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