Diphenylpyraline

Diphenylpyraline (DPP; sold as Allergen, Arbid, Belfene, Diafen, Hispril, Histyn, Lergobine, Lyssipol, Mepiben, Neargal) is a first-generation antihistamine with anticholinergic effects of the diphenylpiperidine class.^[2][3][4] It is marketed in Europe for the treatment of allergies.^[2][3][5] DPP has also been found to act as a dopamine reuptake inhibitor and produces hyperactivity in rodents.^[6] It has been shown to be useful in the treatment of Parkinsonism.^[7]

Diphenylpyraline

Clinical data
Other names	4-(diphenylmethoxy)-1-methyl-piperidine
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, Topical
ATC code	R06AA07 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	24–40 hours[1]
Identifiers
IUPAC name 4-benzhydryloxy-1-methyl-piperidine
CAS Number	147-20-6 Y
PubChem CID	3103
IUPHAR/BPS	7165
DrugBank	DB01146 Y
ChemSpider	2992 Y
UNII	33361OE3AV
KEGG	D07862 Y
ChEBI	CHEBI:59788 Y
ChEMBL	ChEMBL1492 Y
CompTox Dashboard (EPA)	DTXSID3022952
ECHA InfoCard	100.005.170
Chemical and physical data
Formula	C19H23NO
Molar mass	281.399 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(C(c1ccccc1)c2ccccc2)C3CCN(C)CC3
InChI InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3 Y Key:OWQUZNMMYNAXSL-UHFFFAOYSA-N Y
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Synthesis

Diphenylpyraline synthesis via coupling of 4-hydroxy-1-methylpiperidine with benzhydrylbromide^[8][9]