Phenbenzamine

Phenbenzamine, sold under the brand name Antergan and known by the former developmental code name RP-2339, is an antihistamine of the ethylenediamine class which also has anticholinergic 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 as mepyramine (pyrilamine; Neoantergan).[5][6] Following this, other antihistamines, such as diphenhydramine, promethazine, and tripelennamine, were developed and introduced.[5][7] Owing to their sedative effects, phenbenzamine and promethazine were assessed in the treatment of manic depression in France 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]

Phenbenzamine
Clinical data
Trade namesAntergan
Other namesRP-2339
Drug classAntihistamine; H1 receptor antagonist
Identifiers
IUPAC name
  • N-(2-Dimethylaminoethyl)-N-benzylaniline
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H22N2
Molar mass254.377 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)CCN(Cc1ccccc1)c2ccccc2
InChI
  • 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 Y
  • Key:CHOBRHHOYQKCOU-UHFFFAOYSA-N Y

Chemistry

Synthesis

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

Phenbenzamine synthesis

References
  1. "Phenbenzamine". Encyclopædia Britannica.
  2. Robert A. Maxwell; Shohreh B. Eckhardt (6 December 2012). Drug Discovery: A Casebook and Analysis. Springer Science & Business Media. pp. 113–. ISBN 978-1-4612-0469-5.
  3. Moncrieff, 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. David A. Williams; William O. Foye; Thomas L. Lemke (2002). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 799–. ISBN 978-0-683-30737-5.
  5. Menizibeya Osain Welcome (20 June 2018). Gastrointestinal Physiology: Development, Principles and Mechanisms of Regulation. Springer. pp. 827–. ISBN 978-3-319-91056-7.
  6. Atta-ur-Rahman (11 July 2018). Frontiers in Clinical Drug Research - Anti-Allergy Agents. Bentham Science Publishers. pp. 29–. ISBN 978-1-68108-337-7.
  7. Ralph Landau; Basil Achilladelis; Alexander Scriabine (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.


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