Back إفيدرين Arabic افدرین AZB Эфедрын Byelorussian Efedrina Catalan Efedrin Czech Effedrin Welsh Efedrin Danish Ephedrin German Εφεδρίνη Greek Efedrino Esperanto

Ephedrine

Not to be confused with ephedrone or epinephrine.

Ephedrine
Chemical structure of the (1R,2S)-ephedrine molecule
Ball-and-stick model of the (1R,2S)-ephedrine molecule
(−)-(1R,2S)-ephedrine chemical structure (top) and ball-and-stick model (bottom)
Clinical data
Pronunciation/ɪˈfɛdrɪn/ or /ˈɛfɪdriːn/
Trade namesAkovaz, 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.comEphedrine: Monograph
HCl: Monograph
Sulfate: Monograph
Pregnancy
category
  • AU: A
Routes of
administration		By mouth, intravenous (IV), intramuscular (IM), subcutaneous (SC)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability88%[6]
Protein binding~24–29% (5–10% to albumin)[7][8][9]
MetabolismLargely unmetabolized[6][10]
Metabolites• Norephedrine[6][10]
Onset of actionOral: 15–60 minutes[11]
IMTooltip Intramuscular injection: 10–20 minutes[11]
IVTooltip Intravenous administration: seconds[11]
Elimination half-life6 hours[6]
Duration of actionOral: 2–4 hours
IV/IM: 60 minutes
ExcretionMainly urine (60% unchanged)[6]
Identifiers
  • (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.528 Edit this at Wikidata
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 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 checkY
  • Key:KWGRBVOPPLSCSI-WPRPVWTQSA-N checkY
  (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]

  1. ^ 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.
  2. ^ "Ephedrine Hydrochloride 15mg Tablets Summary of Product Characteristics (SmPC)". emc. Retrieved 8 October 2020.
  3. ^ "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.
  4. ^ "Akovaz- ephedrine sulfate injection". DailyMed. 16 April 2020. Retrieved 8 October 2020.
  5. ^ "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.
  6. ^ a b c d e "Ephedrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 29 April 2016. Retrieved 14 July 2024.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ a b "Ephedrine Pregnancy and Breastfeeding Warnings". Archived from the original on 5 August 2017. Retrieved 8 October 2017.
  14. ^ Cite error: The named reference PubChem was invoked but never defined (see the help page).
  15. ^ 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.
  16. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 541. ISBN 9783527607495.
  17. ^ 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.
  18. ^ 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.

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