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Phenbenzamine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Phenbenzamine
Clinical data
Trade namesAntergan
Other namesRP-2339
Drug classAntihistamine;H1 receptor antagonist
Identifiers
  • N-(2-Dimethylaminoethyl)-N-benzylaniline
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC17H22N2
Molar mass254.377 g·mol−1
3D model (JSmol)
  • CN(C)CCN(Cc1ccccc1)c2ccccc2
  • InChI=InChI=1S/C17H22N2/c1-18(2)13-14-19(17-11-7-4-8-12-17)15-16-9-5-3-6-10-16/h3-12H,13-15H2,1-2H3 checkY
  • Key:CHOBRHHOYQKCOU-UHFFFAOYSA-N checkY

Phenbenzamine, sold under the brand nameAntergan and known by the former developmental code nameRP-2339, is anantihistamine of theethylenediamine class which also hasanticholinergic properties.[1][2] It was introduced in 1941 or 1942 and was the first antihistamine to be introduced for medical use.[3][4][5] Soon following its introduction, phenbenzamine was replaced by another antihistamine of the same class known asmepyramine (pyrilamine; Neoantergan).[5][6] Following this, other antihistamines, such asdiphenhydramine,promethazine, andtripelennamine, were developed and introduced.[5][7] Owing to theirsedative effects, phenbenzamine and promethazine were assessed in the treatment ofmanic depression inFrance in the 1940s and were regarded as promising therapies for such purposes.[3] Whereas phenbenzamine was the first clinically useful antihistamine,piperoxan was the first compound with antihistamine properties to be discovered and was synthesized in the early 1930s.[7]

Chemistry

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Synthesis

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Phenbenzamine can be prepared by the reaction ofN-benzylaniline with 2-chloroethyldimethylamine.[8][9]

Phenbenzamine synthesis

References

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  1. ^"Phenbenzamine".Encyclopædia Britannica.
  2. ^Maxwell RA, Eckhardt SB (6 December 2012)."Chloropromazine".Drug Discovery: A Casebook and Analysis. Springer Science & Business Media. pp. 113–.ISBN 978-1-4612-0469-5.
  3. ^abMoncrieff, Joanna (2013). "Chlorpromazine: The First Wonder Drug".The Bitterest Pills. Palgrave Macmillan UK. pp. 20–38.doi:10.1057/9781137277442_2.ISBN 978-1-137-27743-5.
  4. ^Williams DA, Foye WO, Lemke TL (2002)."Chapter 29: Estrogen, Progestins, and Androgens".Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 799–.ISBN 978-0-683-30737-5.
  5. ^abcWelcome MO (20 June 2018).Gastrointestinal Physiology: Development, Principles and Mechanisms of Regulation. Springer. pp. 827–.ISBN 978-3-319-91056-7.
  6. ^Cundell DR, Mickle KE (11 July 2018)."Developing the Perfect Antihistamine for use in Allergic Conditions: A Voyage in H1 Selectivity". In Atta-ur-Rahman (ed.).Frontiers in Clinical Drug Research - Anti-Allergy Agents. Bentham Science Publishers. pp. 29–.ISBN 978-1-68108-337-7.
  7. ^abLandau R, Achilladelis B, Scriabine A (1999).Pharmaceutical Innovation: Revolutionizing Human Health. Chemical Heritage Foundation. pp. 230–231.ISBN 978-0-941901-21-5.
  8. ^US 2634293, Kyrides LP, Zienty FB, "Process of preparing a monobasic salt of a secondary amine", issued 7 April 1953, assigned to Monsanto Chemicals 
  9. ^Kaye IA, Parris CL, Weiner N (1953). "A Novel N-Alkylation Reaction".Journal of the American Chemical Society.75 (3):744–745.doi:10.1021/ja01099a508.
Benzimidazoles(*)
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H4
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