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 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 |
|---|---|---|
| Ephedrine-induced complete atrioventricular block with ventricular asystole during rapid concomitant phenytoin infusion: a case report. | 1999 Mar |
|
| 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 |
|
| l-Ephedrine is a major constituent of Mao-Bushi-Saishin-To, one of the formulas of Chinese medicine, which shows immediate inhibition after oral administration of passive cutaneous anaphylaxis in rats. | 2000 Aug |
|
| 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 |
|
| Prevention of generalized reactions to contrast media: a consensus report and guidelines. | 2001 |
|
| 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 |
|
| Mass spectrometric quantitation of chiral drugs by the kinetic method. | 2001 Apr 15 |
|
| Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions. | 2001 Apr 15 |
|
| 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 |
|
| Dietary supplements containing ephedra alkaloids. | 2001 Apr 5 |
|
| 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 |
|
| 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 |
|
| Application of carboxymethyl-beta-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters. | 2001 Aug 17 |
|
| The trouble with fat-burner pills. | 2001 Aug 27 |
|
| Ephedra is linked to CNS, cardiovascular risks. | 2001 Feb |
|
| 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 |
|
| Pre-filled ephedrine syringes. | 2001 Jul |
|
| New observations on the secondary chemistry of world Ephedra (Ephedraceae). | 2001 Jul |
|
| 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 |
|
| Cold-syrup induced movement disorder. | 2001 Jun |
|
| It's a rave new world: rave culture and illicit drug use in the young. | 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 |
|
| [A case of pulmonary embolism associated with pneumatic tourniquet deflation]. | 2001 Mar |
|
| Venlafaxine occupation at the noradrenaline reuptake site: in-vivo determination in healthy volunteers. | 2001 Mar |
|
| High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities. | 2001 Mar |
|
| Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters by Mannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines. | 2001 Mar 8 |
|
| Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man. | 2001 May |
|
| Fulminant exacerbation of autoimmune hepatitis after the use of ma huang. | 2001 May |
|
| Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr. | 2001 May |
|
| Neuropeptide Y in obese women during treatment with adrenergic modulation drugs. | 2001 May-Jun |
|
| Pharmacologic options available to treat symptomatic intradialytic hypotension. | 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 |
|
| Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations. | 2001 Sep |
|
| Phenylephrine added to prophylactic ephedrine infusion during spinal anesthesia for elective cesarean section. | 2001 Sep |
|
| What constitutes an effective but safe initial dose of lidocaine to test a thoracic epidural catheter? | 2001 Sep |
|
| Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations. | 2001 Sep |
|
| Rapid chiral on-chip separation with simplified amperometric detection. | 2001 Sep 14 |
|
| [Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit]. | 2001 Sep 24 |
|
| A history of nebulization. | 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
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 UTC 2023
by
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on
Fri Dec 15 15:09:30 UTC 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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71587013
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ACTIVE MOIETY |