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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
Structure of EPHEDRINE CAMPHORATE

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P07550|||Q53GA6|||Q9UCZ3
Gene ID: 154.0
Gene Symbol: ADRB2
Target Organism: Homo sapiens (Human)
0.36 µM [EC50]
4.95 null [pKi]
Target ID: P08588
Gene ID: 153.0
Gene Symbol: ADRB1
Target Organism: Homo sapiens (Human)
0.5 µM [EC50]
4.83 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AKOVAZ

Approved Use

AKOVAZ 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 Date

2016
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
79.4 ng/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
6.75 h
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
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

PubMed

TitleDatePubMed
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
Patents

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
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 Fri Dec 15 15:09:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:30 GMT 2023
Record UNII
W56S9O8P5Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPHEDRINE CAMPHORATE
Common Name English
EPHEDRINE, COMPD. WITH CAMPHORIC ACID (1:1), L-(+)-
Common Name English
1,3-CYCLOPENTANEDICARBOXYLIC ACID, 1,2,2-TRIMETHYL-, (1R,2S)-, COMPD. WITH (.ALPHA.R)-.ALPHA.-((1S)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL (1:1)
Common Name English
CAMPHORIC ACID, COMPD. WITH EPHEDRINE (1:1)
Common Name English
Code System Code Type Description
CAS
17140-28-2
Created by admin on Fri Dec 15 15:09:30 GMT 2023 , Edited by admin on Fri Dec 15 15:09:30 GMT 2023
PRIMARY
FDA UNII
W56S9O8P5Y
Created by admin on Fri Dec 15 15:09:30 GMT 2023 , Edited by admin on Fri Dec 15 15:09:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID40169084
Created by admin on Fri Dec 15 15:09:30 GMT 2023 , Edited by admin on Fri Dec 15 15:09:30 GMT 2023
PRIMARY
PUBCHEM
71587013
Created by admin on Fri Dec 15 15:09:30 GMT 2023 , Edited by admin on Fri Dec 15 15:09:30 GMT 2023
PRIMARY
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ACTIVE MOIETY