Medication and stimulant
Pharmaceutical compound
Ephedrine (−)-(1R ,2S )-ephedrine chemical structure (top) and ball-and-stick model (bottom)
Pronunciation or Trade names Akovaz, Corphedra, Emerphed, others Other names (−)-Ephedrine; (1R ,2S )-Ephedrine; (1R ,2S )-β-Hydroxy-N -methylamphetamine; (1R ,2S )-β-Hydroxy-N -methyl-α-methyl-β-phenethylamine AHFS /Drugs.com Ephedrine: Monograph HCl: Monograph Sulfate: Monograph Pregnancy category Routes of administration By mouth , intravenous (IV), intramuscular (IM), subcutaneous (SC)ATC code Legal status
Bioavailability 88%[ 6] Protein binding ~24–29% (5–10% to albumin )[ 7] [ 8] [ 9] Metabolism Largely unmetabolized[ 6] [ 10] Metabolites • Norephedrine [ 6] [ 10] Onset of action Oral : 15–60 minutes[ 11] IM Tooltip Intramuscular injection : 10–20 minutes[ 11] IV Tooltip Intravenous administration : Rapid[ 11] Elimination half-life 6 hours[ 6] Duration of action Oral : 2–4 hours IV/IM: 60 minutesExcretion Mainly urine (60% unchanged)[ 6]
(1R ,2S )-2-(methylamino)-1-phenylpropan-1-ol
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.005.528 Formula C 10 H 15 N O Molar mass 165.236 g·mol−1 3D model (JSmol )
C[C@@H]([C@@H](C1=CC=CC=C1)O)NC
InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1
Y Key:KWGRBVOPPLSCSI-WPRPVWTQSA-N
Y
(verify)
Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent low blood pressure during anesthesia .[ 11] It has also been used for asthma , narcolepsy , and obesity but is not the preferred treatment.[ 11] It is of unclear benefit in nasal congestion .[ 11] It can be taken by mouth or by injection into a muscle , vein , or just under the skin .[ 11] Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect.[ 11] When given by injection, it lasts about an hour, and when taken by mouth, it can last up to four hours.[ 11]
Common side effects include trouble sleeping , anxiety , headache , hallucinations , high blood pressure , fast heart rate , loss of appetite , and urinary retention .[ 11] Serious side effects include stroke and heart attack .[ 11] While likely safe in pregnancy , its use in this population is poorly studied.[ 12] [ 13] Use during breastfeeding is not recommended.[ 13] Ephedrine works by inducing the release of norepinephrine and hence indirectly activating the α- and β-adrenergic receptors .[ 11] Chemically, ephedrine is a substituted amphetamine and is the (1R ,2S )-enantiomer of β-hydroxy-N -methylamphetamine .[ 14]
Ephedrine was first isolated in 1885 and came into commercial use in 1926.[ 15] [ 16] It is on the World Health Organization's List of Essential Medicines .[ 17] It is available as a generic medication .[ 11] It can normally be found in plants of the Ephedra genus.[ 11] [ 18] Over-the-counter dietary supplements containing ephedrine are illegal in the United States ,[ 11] with the exception of those used in traditional Chinese medicine , where its presence is noted by má huáng .[ 11] [ 18]
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15 .
^ "Ephedrine Hydrochloride 15mg Tablets Summary of Product Characteristics (SmPC)" . emc . Retrieved 8 October 2020 .
^ "Ephedrine Nasal Drops 1.0% Summary of Product Characteristics (SmPC)" . emc . 11 March 2015. Archived from the original on 24 October 2020. Retrieved 8 October 2020 .
^ "Akovaz- ephedrine sulfate injection" . DailyMed . 16 April 2020. Retrieved 8 October 2020 .
^ "Title 21: Food And Drugs Part 341—Cold, Cough, Allergy, Bronchodilator, And Antiasthmatic Drug Products For Over-The-Counter Human Use" . Electronic Code of Federal Regulations . Retrieved 8 October 2020 .
^ a b c d e "Ephedrine: Uses, Interactions, Mechanism of Action" . DrugBank Online . 29 April 2016. Retrieved 14 July 2024 .
^ Volpp M, Holzgrabe U (January 2019). "Determination of plasma protein binding for sympathomimetic drugs by means of ultrafiltration". Eur J Pharm Sci . 127 : 175–184. doi :10.1016/j.ejps.2018.10.027 . PMID 30391401 .
^ Schmidt S (2023). Lang-etablierte Arzneistoffe genauer unter die Lupe genommen: Enantioselektive Proteinbindung und Stabilitätsstudien [A closer look at long-established drugs: enantioselective protein binding and stability studies ] (Thesis) (in German). Universität Würzburg. doi :10.25972/opus-34594 .
^ Gad MZ, Azab SS, Khattab AR, Farag MA (October 2021). "Over a century since ephedrine discovery: an updated revisit to its pharmacological aspects, functionality and toxicity in comparison to its herbal extracts". Food Funct . 12 (20): 9563–9582. doi :10.1039/d1fo02093e . PMID 34533553 .
^ a b Chua SS, Benrimoj SI, Triggs EJ (1989). "Pharmacokinetics of non-prescription sympathomimetic agents". Biopharm Drug Dispos . 10 (1): 1–14. doi :10.1002/bdd.2510100102 . PMID 2647163 .
^ a b c d e f g h i j k l m n o p "Ephedrine" . The American Society of Health-System Pharmacists. Archived from the original on 2017-09-09. Retrieved 8 September 2017 .
^ Briggs GG, Freeman RK, Yaffe SJ (2011). Drugs in pregnancy and lactation: a reference guide to fetal and neonatal risk (9th ed.). Philadelphia: Lippincott Williams & Wilkins. p. 495. ISBN 9781608317080 . Archived from the original on 2017-09-08.
^ a b "Ephedrine Pregnancy and Breastfeeding Warnings" . Archived from the original on 5 August 2017. Retrieved 8 October 2017 .
^ Cite error: The named reference PubChem
was invoked but never defined (see the help page ).
^ Soni MG, Shelke K, Amin R, Talati (2013). "A Lessons from the Use of Ephedra Products as a Dietary Supplement" . In Bagchi D, Preuss HG (eds.). Obesity epidemiology, pathophysiology, and prevention (2nd ed.). Boca Raton, Florida: CRC Press. p. 692. ISBN 9781439854266 . Archived from the original on 2017-09-08.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery . John Wiley & Sons. p. 541. ISBN 9783527607495 .
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021) . Geneva: World Health Organization. hdl :10665/345533 . WHO/MHP/HPS/EML/2021.02.
^ a b Abourashed EA, El-Alfy AT, Khan IA, Walker L (August 2003). "Ephedra in perspective—a current review". Phytotherapy Research . 17 (7): 703–712. doi :10.1002/ptr.1337 . PMID 12916063 . S2CID 41083359 .