Structure via PubChem · Public domain (PubChem)
piperoxan
Sign in to savePiperoxan, also known as benodaine, was the first antihistamine to be discovered. This compound, derived from benzodioxan, was prepared in the early 1930s by Daniel Bovet and Ernest Fourneau at the Pasteur Institute in France. Formerly investigated by Fourneau as an α-adrenergic-blocking agent, they demonstrated that it also antagonized histamine-induced bronchospasm in guinea pigs, and published their findings in 1933. Bovet went on to win the 1957 Nobel Prize in Physiology or Medicine for his contribution. One of Bovet and Fourneau's students, Anne-Marie Staub, published the first structure–
Chemical data
- Formula
- C14H19NO2
- Molecular weight
- 233.31 g/mol
- IUPAC name
- 1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)piperidine
- SMILES
- C1CCN(CC1)CC2COC3=CC=CC=C3O2
- InChIKey
- LYKMMUBOEFYJQG-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 21.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
346 papers- The effects of piperoxan on uptake of noradrenaline and overflow of transmitter in the isolated blood perfused spleen of the cat.British journal of pharmacology · 1978
- Brainstem mechanisms in the modulation of the sympathetic baroreflex by piperoxan.European journal of pharmacology · 1988
- [Comparative study of piperoxan and 2-(2-imidazolinyl)-1, 4-benzodioxane (170 150) on pre- and postsynaptic receptors in the rat].Journal de pharmacologie · 1982
- Hypertensive crisis and severe myocardial ischemia induced by piperoxan, with comments on the differential diagnosis and treatment of hypertensive crisis.Angiology · 1954
- Piperoxan hydrochloride (benzodioxan) test; report of a false positive reaction.Journal of the American Medical Association · 1951
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 233.142
Show 4 more facts
- chemical formula
- C₁₄H₁₉NO₂
- canonical SMILES
- C1CCN(CC1)CC2COC3=CC=CC=C3O2
- subject has role
- antihypertensive drug
- Commons category
- Piperoxan
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Piperoxan, also known as benodaine, was the first antihistamine to be discovered. This compound, derived from benzodioxan, was prepared in the early 1930s by Daniel Bovet and Ernest Fourneau at the Pasteur Institute in France. Formerly investigated by Fourneau as an α-adrenergic-blocking agent, they demonstrated that it also antagonized histamine-induced bronchospasm in guinea pigs, and published their findings in 1933. Bovet went on to win the 1957 Nobel Prize in Physiology or Medicine for his contribution. One of Bovet and Fourneau's students, Anne-Marie Staub, published the first structure–activity relationship (SAR) study of antihistamines in 1939. Piperoxan and analogues themselves were not clinically useful due to the production of toxic effects in humans and were followed by phenbenzamine (Antergan) in the early 1940s, which was the first antihistamine to be marketed for medical use.
==Synthesis== thumb|center|601px|class=skin-invert-image|Synthesis: Patent:
Excerpted from Wikipedia’s “piperoxan” article, available under the CC BY-SA 4.0 licence.