Ephedrine

Ephedrine
Clinical data

(1R,2S)-(−)-ephedrine (top), (1S,2R)-(+)-ephedrine (center and bottom)
Pronunciation	ⁱ/ᵻˈfɛdrɪn/ or /ˈɛfᵻdriːn/
Trade names	Bronkaid, Primatene
AHFS/Drugs.com	Monograph
Pregnancy category	AU: A US: C (Risk not ruled out)
Routes of administration	by mouth, IV, IM, 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: Pharmacy medicines US: List I OTC, Schedule III (OR)
Pharmacokinetic data
Bioavailability	85%
Metabolism	minimal liver
Onset of action	IV (seconds), IM (10 min to 20 min), by mouth (15 min to 60 min)
Biological half-life	3 h to 6 h
Duration of action	IV/IM (60 min), by mouth (2 h to 4 h)
Excretion	22% to 99% (urine)
Identifiers
IUPAC name rel-(R,S)-2-(methylamino)-1-phenylpropan-1-ol
CAS Number	299-42-3^Y
PubChem (CID)	5032
IUPHAR/BPS	556
DrugBank	DB01364^Y
ChemSpider	8935^N
UNII	7CUC9DDI9F^N
KEGG	D00124^Y
ChEBI	CHEBI:15407^Y
ChEMBL	CHEMBL211456^Y
ECHA InfoCard	100.005.528
Chemical and physical data
Formula	C₁₀H₁₅NO
Molar mass	165.23
3D model (Jmol)	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^Y Key:KWGRBVOPPLSCSI-WPRPVWTQSA-N^Y
^NY (what is this?)

Ephedrine is a medication used to prevent low blood pressure during spinal anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 min, and by mouth can take an hour for effect. When given by injection it lasts about an hour and when taken by mouth it can last up to four hours.

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

Ephedrine was first isolated in 1885. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is about 0.69 to 1.35 USD per dose. In the United States it is not very expensive. It can normally be found in plants of the Ephedra type. Dietary supplements that contain ephedrine are illegal in the United States. An exception is when used in traditional Chinese medicine.

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Wikipedia