Phenbenzamine

Chemical compound From Wikipedia, the free encyclopedia

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]

Trade namesAntergan
Other namesRP-2339
CAS Number
Quick facts Clinical data, Trade names ...
Phenbenzamine
Clinical data
Trade namesAntergan
Other namesRP-2339
Drug classAntihistamine; H1 receptor antagonist
Identifiers
  • 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)
  • CN(C)CCN(Cc1ccccc1)c2ccccc2
  • 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
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Chemistry

Synthesis

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

Phenbenzamine synthesis

References

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