Ephedrine hydrochloride

US Approved OTC

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

Structure Search

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

HIDE SMILES / InChI

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

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf | https://www.rcpe.ac.uk/sites/default/files/lee_0.pdf

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	Potency
Beta-2 adrenergic receptor 203 Target ID: P07550\|\|\|Q53GA6\|\|\|Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2662	0.36 µM [EC50]
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2662	4.95 null [pKi]
Beta-1 adrenergic receptor 158 Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2662	0.5 µM [EC50]
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2662	4.83 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anesthesia-induced hypotension 10 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Primary		Approved 8360	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 1.46188796E12

C_max

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

T_1/2

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

Sourcing

Vendor/Aggregator	ID	URL
Achemtek	0104-020654	http://www.achemtek.com/299-42-3
Acorn PharmaTech	ACN-037777	http://www.acornpharmatech.com/
Aurora Fine Chemicals LLC	A17.887.833	http://online.aurorafinechemicals.com/info?ID=A17.887.833
BioSynth	J-500280	https://www.biosynth.com/en/products/all-products/products/J-500280.html
Capot Chemical	PubChem5778	http://www.capotchem.com/en/5778.htm
Chem Scene	CS-4802	http://www.chemscene.com/Ephedrine.html
ChemMol	99067321	http://www.chemmol.com/chemmol/99067321.html
MedChem Express	HY-B1195	http://www.medchemexpress.com/Ephedrine.html
OChem	2694	http://www.ocheminc.com/index.php?act=psearch&pid=299E423
Parchem	26857	http://www.parchem.com/chemical-supplier-distributor/Ephedrine-016857.aspx
Sigma-Aldrich	134910_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/134910?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S007941	http://www.smolecule.com/products/s007941
Smolecule	S527246	http://www.smolecule.com/products/s527246
THE BioTek	bt-255443	https://www.thebiotek.com/product/inhibitors/bt-255443
THE BioTek	bt-267449	https://www.thebiotek.com/product/inhibitors/bt-267449
iChemical	EBD2203043	http://www.ichemical.com/products/299-42-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-1217859840	https://mcule.com/MCULE-1217859840/

PubMed

Title	Date	PubMed
Prevention of generalized reactions to contrast media: a consensus report and guidelines.	2001	11511894
Recurrent ischaemic colitis associated with pseudoephedrine use.	2001 Apr	11478350
The effects of ginseng, ephedrine, and caffeine on cognitive performance, mood and energy.	2001 Apr	11368507
[Misuse of drugs in recreational sports].	2001 Apr	11344954
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
The many faces of ecstasy.	2001 Apr	11317061
Mass spectrometric quantitation of chiral drugs by the kinetic method.	2001 Apr 15	11338581
Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions.	2001 Apr 15	11338580
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	11358226
Dietary supplements containing ephedra alkaloids.	2001 Apr 5	11291669
Dietary supplements containing ephedra alkaloids.	2001 Apr 5	11291668
Phenylpropanolamine and hemorrhagic stroke.	2001 Apr 5	11291667
Ondansetron versus dehydrobenzoperidol and metoclopramide for management of postoperative nausea in laparoscopic surgery patients.	2001 Apr-Jun	11394426
Role of the atrial natriuretic factor in obstetric spinal hypotension.	2001 Aug	11506108
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section.	2001 Aug	11506099
Effect of caffeine and ephedrine ingestion on anaerobic exercise performance.	2001 Aug	11474345
Application of carboxymethyl-beta-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters.	2001 Aug 17	11556337
Use of nonprescription weight loss products: results from a multistate survey.	2001 Aug 22-29	11509057
The trouble with fat-burner pills.	2001 Aug 27	11534484
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.	2001 Jan	11575417
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training.	2001 Jul	11583395
Pre-filled ephedrine syringes.	2001 Jul	11463045
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 Jul	11461968
A stable gas chromatography-mass spectrometry analysis system to characterize Ma Huang products found in health foods and supplements.	2001 Jul	11458341
New observations on the secondary chemistry of world Ephedra (Ephedraceae).	2001 Jul	11454619
Reappearance of cardiac presynaptic sympathetic nerve terminals in the transplanted heart: correlation between PET using (11)C-hydroxyephedrine and invasively measured norepinephrine release.	2001 Jul	11438620
Hypotension in spinal anesthesia for cesarean section: a comparison of 0.5% hyperbaric bupivacaine and 5% hyperbaric lidocaine.	2001 Jun	11529341
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations.	2001 Jun	11377047
Reduced myocardial carbon-11 hydroxyephedrine retention is associated with poor prognosis in chronic heart failure.	2001 Mar	11315607
[A case of pulmonary embolism associated with pneumatic tourniquet deflation].	2001 Mar	11296445
[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus].	2001 Mar 20	11332378
Comparative oral and topical decongestant effects of phenylpropanolamine and d-pseudoephedrine.	2001 Mar-Apr	11345158
Extra-strong graduated compression stocking reduces usage of vasopressor agents during spinal anesthesia for cesarean section.	2001 May	11409475
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man.	2001 May	11381283
Fulminant exacerbation of autoimmune hepatitis after the use of ma huang.	2001 May	11374728
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.	2001 May	11361053
Seizure activity and unresponsiveness after hydroxycut ingestion.	2001 May	11349754
Over-the-counter drug use in gymnasiums: an underrecognized substance abuse problem?	2001 May-Jun	11340414
Pharmacologic options available to treat symptomatic intradialytic hypotension.	2001 Oct	11602458
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	11559922
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations.	2001 Sep	11593992
Phenylephrine added to prophylactic ephedrine infusion during spinal anesthesia for elective cesarean section.	2001 Sep	11575540
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry.	2001 Sep	11565946
What constitutes an effective but safe initial dose of lidocaine to test a thoracic epidural catheter?	2001 Sep	11524351
Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations.	2001 Sep	11470203
Rapid chiral on-chip separation with simplified amperometric detection.	2001 Sep 14	11587341
[Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit].	2001 Sep 24	11590951
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes.	2001 Sep 5	11530984
Effect of sympathetic reinnervation on cardiac performance after heart transplantation.	2001 Sep 6	11547742
New imaging techniques for cardiovascular autonomic neuropathy: a window on the heart.	2001 Spring	11469712

Patents

Sample Use Guides

In Vivo Use Guide

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 `Thu Jul 06 00:03:17 UTC 2023` Edited by `admin` on `Thu Jul 06 00:03:17 UTC 2023`
Record UNII	NLJ6390P1Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Ephedrine hydrochloride

Common Name

English

EPHEDRINE HYDROCHLORIDE [MART.]

Common Name

English

EPHEDRINE HYDROCHLORIDE [VANDF]

Common Name

English

L-EPHEDRINE HYDROCHLORIDE

Common Name

English

EPHEDRINE HYDROCHLORIDE [JAN]

Common Name

English

EPHEDRINE HYDROCHLORIDE [WHO-IP]

Common Name

English

(R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL HYDROCHLORIDE [WHO-IP]

Systematic Name

English

EPHEDRINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, HYDROCHLORIDE, (R-(R*,S*))-

Common Name

English

REZIPRES

Brand Name

English

EPHEDRINE HYDROCHLORIDE [MI]

Common Name

English

EPHEDRINE HYDROCHLORIDE [EP IMPURITY]

Common Name

English

EPHEDRINI HYDROCHLORIDUM [WHO-IP LATIN]

Common Name

English

NSC-759611

Code

English

EPHEDRINE HYDROCHLORIDE [USP-RS]

Common Name

English

EPHEDRINE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

(-)-EPHEDRINE HYDROCHLORIDE [WHO-IP]

Common Name

English

EPHEDRINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

(-)-EPHEDRINE HYDROCHLORIDE

Common Name

English

Ephedrine hydrochloride [WHO-DD]

Common Name

English

EPHEDRINE HCL

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 341.20