Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H15NO.ClH |
| Molecular Weight | 201.693 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN[C@@H](C)[C@H](O)C1=CC=CC=C1
InChI
InChIKey=BALXUFOVQVENIU-GNAZCLTHSA-N
InChI=1S/C10H15NO.ClH/c1-8(11-2)10(12)9-6-4-3-5-7-9;/h3-8,10-12H,1-2H3;1H/t8-,10-;/m0./s1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
|---|---|---|
| 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 |
|
| 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 |
|
| 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 |
|
| Phenylpropanolamine and hemorrhagic stroke. | 2001 Apr 5 |
|
| Ondansetron versus dehydrobenzoperidol and metoclopramide for management of postoperative nausea in laparoscopic surgery patients. | 2001 Apr-Jun |
|
| Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section. | 2001 Aug |
|
| Dose of prophylactic intravenous ephedrine during spinal anesthesia for cesarean section. | 2001 Aug |
|
| Prevention and management of hypotension during spinal anaesthesia for elective Caesarean section: a survey of practice. | 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 |
|
| Continuous production of (R)-phenylacetylcarbinol in an enzyme-membrane reactor using a potent mutant of pyruvate decarboxylase from Zymomonas mobilis. | 2001 Aug 20 |
|
| Use of nonprescription weight loss products: results from a multistate survey. | 2001 Aug 22-29 |
|
| Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients. | 2001 Jan |
|
| The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training. | 2001 Jul |
|
| Pre-filled ephedrine syringes. | 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 |
|
| Spinal anaesthesia for Caesarean section with bupivacaine 5 mg ml(-1) in glucose 8 or 80 mg ml(-1). | 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 |
|
| 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 |
|
| Evaluation of pre-emptive intramuscular phenylephrine and ephedrine for reduction of spinal anaesthesia-induced hypotension during Caesarean section. | 2001 Mar |
|
| High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities. | 2001 Mar |
|
| Extra-strong graduated compression stocking reduces usage of vasopressor agents during spinal anesthesia for cesarean section. | 2001 May |
|
| 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 |
|
| Determination of ephedrine-type alkaloids in dietary supplements by LC/MS using a stable-isotope labeled internal standard. | 2001 May-Jun |
|
| 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 |
|
| Pharmacologic options available to treat symptomatic intradialytic hypotension. | 2001 Oct |
|
| 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 |
|
| 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 |
|
| Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry. | 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 |
|
| 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 |
|
| 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 |
|
| A history of nebulization. | 2001 Spring |
|
| 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
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 16:38:04 GMT 2023
by
admin
on
Fri Dec 15 16:38:04 GMT 2023
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| Record UNII |
NLJ6390P1Z
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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CFR |
21 CFR 341.20
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NCI_THESAURUS |
C29747
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CFR |
21 CFR 341.16
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CFR |
21 CFR 349.18
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50-98-6
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m4933
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200-074-6
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CHEMBL211456
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SUB13686MIG
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NLJ6390P1Z
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NLJ6390P1Z
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65326
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91165
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759611
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C75031
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1235999
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DTXSID1045825
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EPHEDRINE HYDROCHLORIDE
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PRIMARY | Description: Colourless crystals or a white, crystalline powder; odourless.Solubility: Soluble in 4 parts of water; soluble in ethanol (~750 g/l) TS; practically insoluble in ether R.Category: Antiasthmatic drug.Storage: Ephedrine hydrochloride should be kept in a well-closed container, protected from light.Additional information: Ephedrine hydrochloride darkens on exposure to light.RequirementsDefinition: Ephedrine hydrochloride contains not less than 99.0% and not more than 101.0% of C10H15NO,HCl, calculated withreference to the dried substance. | ||
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DBSALT001513
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100000091342
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| Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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|
PARENT -> SALT/SOLVATE | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |