File:Ephedrine_v2.svg · Wikimedia Commons · See Wikimedia Commons
(−)-ephedrine
Sign in to saveAlso known as L(-)-ephedrine, L-erythro-2-(methylamino)-1-phenylpropan-1-ol, l-ephedrine, L(−)-ephedrine, (-)-ephedrine, (1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropane, L-ephedrine, ephedrine
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AI-generated from the Wikipedia summary — may contain errors.
Key facts
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 464189705
- Drug.image
- Ephedrine v2.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.alt
- Chemical structure of the (1R,2S)-ephedrine molecule
- Drug.image2
- (1R,2S)-Ephedrine molecule from xtal ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 225px
- Drug.alt2
- Ball-and-stick model of the (1R,2S)-ephedrine molecule
- Drug.caption
- (−)-(1R,2S)-ephedrine chemical structure (top) and ball-and-stick model (bottom)
- Drug.pronounce
- or
- Drug.tradename
- Akovaz, Corphedra, Emerphed, others
- Drug.Drugs.com
- Ephedrine: HCl: Sulfate:
- Drug.pregnancy_AU
- A
- Drug.dependency_liability
- Low Psychological: Moderate
- Drug.addiction_liability
- Moderate
via Wikipedia infobox
Chemical data
- Formula
- C10H15NO
- Molecular weight
- 165.23 g/mol
- IUPAC name
- (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
- SMILES
- C[C@@H]([C@@H](C1=CC=CC=C1)O)NC
- InChIKey
- KWGRBVOPPLSCSI-WPRPVWTQSA-N
- XLogP
- 0.9
- Polar surface area
- 32.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 165.115364
Show 9 more facts
- chemical formula
- C₁₀H₁₅NO
- World Health Organisation international non-proprietary name
- ephedrine
- canonical SMILES
- CC(C(C1=CC=CC=C1)O)NC
- isomeric SMILES
- C[C@@H]([C@@H](C1=CC=CC=C1)O)NC
- decomposition point
- 225
- defined daily dose
- 50
- melting point
- 40
- stylized name
- ePHEDrine
- Commons category
- L-Ephedrine
Sources (9)
via Wikidata · CC0
~25 min read
Article
37 sectionsContents
- Medical uses
- Weight loss
- Available forms
- Contraindications
- Side effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Chemistry
- Nomenclature
- Detection in body fluids
- History
- Asia
- Western medicine
- Society and culture
- Names
- Recreational use
- Use in exercise and sports
- Other uses
- Legal status
- Canada
- United States
- Australia
- South Africa
- Germany
- Production
- Agricultural
- Synthetic
- Biosynthetic
- References
- External links
Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. 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 20minutes, 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 urinary retention. Serious side effects include stroke and heart attack. While probably safe in pregnancy, its use in this population is poorly studied. Use during breastfeeding is not recommended. Ephedrine works by inducing the release of norepinephrine and hence indirectly activating the α- and β-adrenergic receptors. Chemically, ephedrine is a substituted amphetamine and is the (1R,2S)-enantiomer of β-hydroxy-N-methylamphetamine.