File:Pethidine2DACS.svg · Wikimedia Commons · See Wikimedia Commons
pethidine
Sign in to saveAlso known as meperidine
Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a fully synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eisleb, its analgesic properties were first recognized by Otto Schaumann while working for IG Farben, in Germany. Pethidine is the prototype of a large family of analgesics including the pethidine 4-phenylpiperidines (e.g., piminodine, anileridine), the prodines (e.g., alphaprodine, MPPP), bemidones (e.g., ketobemidone), and others more distant, inclu
Chemical data
- Formula
- C15H21NO2
- Molecular weight
- 247.33 g/mol
- IUPAC name
- ethyl 1-methyl-4-phenylpiperidine-4-carboxylate
- SMILES
- CCOC(=O)C1(CCN(CC1)C)C2=CC=CC=C2
- InChIKey
- XADCESSVHJOZHK-UHFFFAOYSA-N
- XLogP
- 2.5
- Polar surface area
- 29.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
8,226 papers- Epidural pethidine: pharmacology and clinical experience.Anaesthesia and intensive care · 1998
- Pethidine.British medical journal · 1947
- Is Pethidine Safe during Labor? Systematic Review.Revista brasileira de ginecologia e obstetricia : revista da Federacao Brasileira das Sociedades de Ginecologia e Obstetricia · 2017
- Clinical pharmacokinetics of pethidine.Clinical pharmacokinetics · 1978
- Intrathecal pethidine: pharmacology and clinical applications.Anaesthesia and intensive care · 1998
via PubMed
Wikidata facts
- Mass
- 247.157229
Show 4 more facts
- MCN code
- 2933.33.81
- chemical formula
- C₁₅H₂₁NO₂
- Commons category
- Pethidine
- canonical SMILES
- CCOC(=O)C1(CCN(CC1)C)C2=CC=CC=C2
via Wikidata · CC0
~13 min read
Article
12 sectionsContents
- Medical uses
- Adverse effects
- Interactions
- Mechanism of action
- Pharmacokinetics
- Recreational use
- Trends
- Synthesis
- Control
- Society and culture
- See also
- References
Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a fully synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eisleb, its analgesic properties were first recognized by Otto Schaumann while working for IG Farben, in Germany. Pethidine is the prototype of a large family of analgesics including the pethidine 4-phenylpiperidines (e.g., piminodine, anileridine), the prodines (e.g., alphaprodine, MPPP), bemidones (e.g., ketobemidone), and others more distant, including diphenoxylate and analogues.
Pethidine is indicated for the treatment of moderate to severe pain, and is delivered as a hydrochloride salt in tablets, as a syrup, or by intramuscular, subcutaneous, or intravenous injection. For much of the 20th century, pethidine was the opioid of choice for many physicians; in 1975, 60% of doctors prescribed it for acute pain and 22% for chronic severe pain.