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 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

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

Phenbenzamine synthesis