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.