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Compound

Piperoxan

Also called Benodaine, Fourneau-933, Piperidinomethylbenzodioxan

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Overview

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.[1–5] WP

Chemistry

Formula
C14H19NO2 PC
CAS number
59-39-2 PC
Molar mass (g/mol)
233.31 PC
IUPAC name (computed by PubChem)
1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)piperidine PC
SMILES
C1CCN(CC1)CC2COC3=CC=CC=C3O2 PC
InChIKey
LYKMMUBOEFYJQG-UHFFFAOYSA-N PC
PubChem CID
6040
IUPAC name
1-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)piperidine WP

Harm reduction information

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Sources

  1. Other Scriabine A, Landau R, Achilladelis B. Pharmaceutical innovation: revolutionizing human health. 1999
  2. Other Nelson WL. Foye's Principles of Medicinal Chemistry. 2008
  3. Journal / agency Fourneau E, Bovet D. Recherches sur l'action sympathicolytique d'un nouveau dérivé du dioxane. Archives Internationales de Pharmacodynamie et de Thérapie. 1933
  4. Other Daniel Bovet
  5. Other Landau R, Achilladelis B, Scriabine A. Pharmaceutical Innovation: Revolutionizing Human Health. 1999

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.