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Ephedrine information


Ephedrine
Ephedrine enantiomers.svg
Ball-and-stick model of the (1S,2R)-ephedrine molecule
(−)-(1R,2S)-ephedrine (top),
(+)-(1S,2R)-ephedrine (center and bottom)
Clinical data
Pronunciation/ɪˈfɛdrɪn/ (Ephedrinelisten) or /ˈɛfɪdrn/
Trade namesAkovaz, Corphedra, Emerphed, others
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
  • C01CA26 (WHO) R01AA03 (WHO), R01AB05 (WHO) (combinations), R03CA02 (WHO), S01FB02 (WHO), QG04BX90 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: Schedule VI
  • UK: POM (Prescription only) / P[1][2]
  • US: ℞-only / OTC[3][4]
Pharmacokinetic data
Bioavailability85%
MetabolismMinimal liver
Onset of actionIV (seconds), IM (10 min to 20 min), by mouth (15 min to 60 min)[5]
Elimination half-life3 h to 6 h
Duration of actionIV/IM (60 min), by mouth (2 h to 4 h)
Excretion22% to 99% (urine)
Identifiers
IUPAC name
  • rel-(R,S)-2-(methylamino)-1-phenylpropan-1-ol
CAS Number
  • 299-42-3 checkY
  • as sulfate: 134-72-5 checkY
PubChem CID
  • 9294
IUPHAR/BPS
  • 556
DrugBank
  • DB01364 checkY
ChemSpider
  • 8935 ☒N
  • as sulfate: 4514262 ☒N
UNII
  • GN83C131XS
  • as sulfate: U6X61U5ZEG
KEGG
  • D00124 checkY
  • as sulfate: D04018 checkY
ChEBI
  • CHEBI:15407 checkY
ChEMBL
  • ChEMBL211456 checkY
  • as sulfate: ChEMBL1523964 checkY
CompTox Dashboard (EPA)
  • DTXSID0022985 Edit this at Wikidata
ECHA InfoCard100.005.528 Edit this at Wikidata
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O[C@H](c1ccccc1)[C@@H](NC)C
InChI
  • 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
 ☒NcheckY (what is this?)  (verify)

Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia.[5] It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment.[5] It is of unclear benefit in nasal congestion.[5] It can be taken by mouth or by injection into a muscle, vein, or just under the skin.[5] Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect.[5] When given by injection it lasts about an hour and when taken by mouth it can last up to four hours.[5]

Common side effects include trouble sleeping, anxiety, headache, hallucinations, high blood pressure, fast heart rate, loss of appetite, and inability to urinate.[5] Serious side effects include stroke and heart attack.[5] While likely safe in pregnancy, its use in this population is poorly studied.[6][7] Use during breastfeeding is not recommended.[7] Ephedrine works by increasing the activity of the α and β adrenergic receptors.[5]

Ephedrine was first isolated in 1885 and came into commercial use in 1926.[8][9] It is on the World Health Organization's List of Essential Medicines.[10] It is available as a generic medication.[5] It can normally be found in plants of the Ephedra genus.[5] Dietary supplements containing ephedrine are illegal in the United States,[5] with the exception of those used in traditional Chinese medicine, where its presence is noted by má huáng.[5]

  1. ^ "Ephedrine Hydrochloride 15mg Tablets Summary of Product Characteristics (SmPC)". emc. Retrieved 8 October 2020.
  2. ^ "Ephedrine Nasal Drops 1.0% Summary of Product Characteristics (SmPC)". emc. 11 March 2015. Retrieved 8 October 2020.
  3. ^ "Akovaz- ephedrine sulfate injection". DailyMed. 16 April 2020. Retrieved 8 October 2020.
  4. ^ "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.
  5. ^ a b c d e f g h i j k l m n "Ephedrine". The American Society of Health-System Pharmacists. Archived from the original on 2017-09-09. Retrieved 8 September 2017.
  6. ^ 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.
  7. ^ a b "Ephedrine Pregnancy and Breastfeeding Warnings". Archived from the original on 5 August 2017. Retrieved 8 October 2017.
  8. ^ Debasis Bagchi; Harry G. Preuss, eds. (2013). Obesity epidemiology, pathophysiology, and prevention (2nd ed.). Boca Raton, Florida: CRC Press. p. 692. ISBN 9781439854266. Archived from the original on 2017-09-08.
  9. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 541. ISBN 9783527607495.
  10. ^ 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.

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