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 depressioninFrance 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 names	Antergan
Other names	RP-2339
Drug class	Antihistamine; H₁ receptor antagonist
Identifiers
IUPAC name N-(2-Dimethylaminoethyl)-N-benzylaniline
CAS Number	961-71-7^Y
PubChem CID	13751
ChemSpider	13155^Y
UNII	733W48NG2Q
CompTox Dashboard (EPA)	DTXSID3043863
Chemical and physical data
Formula	C₁₇H₂₂N₂
Molar mass	254.377 g·mol⁻¹
3D model (JSmol)	Interactive image
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

edit

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

Phenbenzamine synthesis

References

^ "Phenbenzamine". Encyclopædia Britannica.

^ 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.

^ ^a ^b 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.

^ 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.

^ ^a ^b ^c Welcome MO (20 June 2018). Gastrointestinal Physiology: Development, Principles and Mechanisms of Regulation. Springer. pp. 827–. ISBN 978-3-319-91056-7.

^ 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.

^ ^a ^b Landau R, Achilladelis B, Scriabine A (1999). Pharmaceutical Innovation: Revolutionizing Human Health. Chemical Heritage Foundation. pp. 230–231. ISBN 978-0-941901-21-5.

^ US 2634293, Kyrides LP, Zienty FB, "Process of preparing a monobasic salt of a secondary amine", issued 7 April 1953, assigned to Monsanto Chemicals

^ 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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Last edited on 8 December 2023,

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