Diphenidol

Antiemetic and antivertigo drug From Wikipedia, the free encyclopedia

Diphenidol is a muscarinic antagonist employed as an antiemetic and as an antivertigo agent. It is not marketed in the United States or Canada.

ATC code
  • none
Quick facts Clinical data, AHFS/Drugs.com ...
Diphenidol
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
Oral
ATC code
  • none
Pharmacokinetic data
Elimination half-life4 hours
Identifiers
  • 1,1-di(phenyl)-4-piperidin-1-ylbutan-1-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.310 Edit this at Wikidata
Chemical and physical data
FormulaC21H27NO
Molar mass309.453 g·mol−1
3D model (JSmol)
  • OC(c1ccccc1)(c2ccccc2)CCCN3CCCCC3
  • InChI=1S/C21H27NO/c23-21(19-11-4-1-5-12-19,20-13-6-2-7-14-20)15-10-18-22-16-8-3-9-17-22/h1-2,4-7,11-14,23H,3,8-10,15-18H2 checkY
  • Key:OGAKLTJNUQRZJU-UHFFFAOYSA-N checkY
  (verify)
Close

Although the mechanism of action of diphenidol on the vestibular system has not yet been elucidated, it exerts an anticholinergic effect due to interactions with mACh receptors, particularly M1, M2, M3 and M4. Hence, its actions may take place at the vestibular nuclei, where a significant excitatory input is mediated by ACh receptors, and also at the vestibular periphery where mACh receptors are expressed at efferent synapses. A series of selective mACh-receptor antagonists based on the diphenidol molecule has been synthesized, but they have not yet been the subject of clinical trials.[1]

Synthesis

Synthesis:[2][3][4][5] 10%:[6] Patents:[7][8][9]

Alkylation of 1-Bromo-3-chloropropane [109-70-6] (1) with piperidine (2) gives 3-Piperidinopropyl chloride [1458-63-5] (3). The Grignard reaction of this intermediate with benzophenone [119-61-9] gives the benzhydrol and hence, Diphenidol (4).

References

Related Articles

Wikiwand AI