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Diphenidol

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Antiemetic and antivertigo drug Pharmaceutical compound
Diphenidol
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral
ATC code
  • none
Pharmacokinetic data
Elimination half-life4 hours
Identifiers
IUPAC name
  • 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
3D model (JSmol)
SMILES
  • OC(c1ccccc1)(c2ccccc2)CCCN3CCCCC3
InChI
  • 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
  • Key:OGAKLTJNUQRZJU-UHFFFAOYSA-N
  (verify)

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

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.

Synthesis

Synthesis: 10%: Patents:

Alkylation of 1-Bromo-3-chloropropane (1) with piperidine (2) gives 3-Piperidinopropyl chloride (3). The Grignard reaction of this intermediate with benzophenone gives the benzhydrol and hence, Diphenidol (4).

References

  1. Soto E, Vega R (March 2010). "Neuropharmacology of vestibular system disorders". Current Neuropharmacology. 8 (1): 26–40. doi:10.2174/157015910790909511. PMC 2866460. PMID 20808544.
  2. Katz, Leon; Karger, Lawrence S. (1952). "The Mannich Reaction on α,α-Diphenylacetone". Journal of the American Chemical Society. 74 (16): 4085–4086. doi:10.1021/ja01136a034.
  3. Gautier, J.A. et al, Bull. Soc. Chim. Fr., 1964, 2145.
  4. Marxer, A. (1941). "Grignard-Reaktionen mit Halogen-alkyl-aminen". Helvetica Chimica Acta. 24 (2): 209E–225E. doi:10.1002/hlca.19410240225.
  5. Vitale, Arturo A.; Doctorovich, F.; Sbarbati Nudelman, N. (1987). "One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums". Journal of Organometallic Chemistry. 332 (1-2): 9–18. doi:10.1016/0022-328X(87)85117-3.
  6. Schmidt, Andreas; Marchetti, Mauro; Eilbracht, Peter (2004). "Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines". Tetrahedron. 60 (50): 11487–11492. doi:10.1016/j.tet.2004.09.058.
  7. Marxer Adrian, Miescher Karl, U.S. patent 2,411,664 (1946 to Ciba Pharmaccutical Products I).
  8. Barrett Paul Anthony & Wilkinson Samuel, GB683950 (1952 to Wellcome Found).
  9. , BE620404 (1961 to SKF Labs).
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