Compound: DIPHENIDOL
SMILES: OC(c1ccccc1)(c2ccccc2)CCCN3CCCCC3
InChIKey: OGAKLTJNUQRZJU-UHFFFAOYSA-N
Synonyms: DIPHENIDOL, Difenidol, 972-02-1, Nometic, Avomol, Difenidolo, Difenidolum, 1,1-Diphenyl-4-(piperidin-1-yl)butan-1-ol, alpha,alpha-Diphenyl-1-piperidinebutanol, Diphenyl(3-(1-piperidyl)propyl)carbinol, SKF 478, SK&F 478, SK&F-478, SK-478, NQO8R319LY, CHEBI:4638, Benzhydrol, alpha-(3-piperidinopropyl)-, DTXSID3022950, 1-Piperidinebutanol, alpha,alpha-diphenyl-, DTXCID502950, RefChem:588811, 213-540-9, SK&F-478-J, Vontrol, diphenadol, Difenidolo [DCIT], Difenidolum [INN-Latin], Diphenidol [USAN], 1,1-diphenyl-4-piperidin-1-ylbutan-1-ol, Difenidol [INN], 1,1-Diphenyl-4-piperidino-1-butanol, 1-Piperidinebutanol, .alpha.,.alpha.-diphenyl-, Difenidol HCl, NCGC00016624-03, 1,1-diphenyl-4-piperidin-1-ylbutan-1-ol hydrochloride, 19-11-4, CAS-972-02-1, HSDB 3316, Deiphenidol Hydrochloride, Diphenidol (USAN/INN), EINECS 213-540-9, UNII-NQO8R319LY, BRN 0265884, 1-Piperidinebutanol, a,a-diphenyl-, DIPHENIDOL [MI], Prestwick0_000252, Prestwick1_000252, Prestwick2_000252, Prestwick3_000252, DIPHENIDOL [HSDB], DIPHENIDOL [VANDF], CHEMBL936, DIFENIDOL [WHO-DD], SCHEMBL34469, BSPBio_000064, SPBio_002283, BPBio1_000072, GTPL7163, orb1705066, OGAKLTJNUQRZJU-UHFFFAOYSA-, SK&F-478A, 1H-INDENE-5-CARBOXYLIC ACID,2,3-DIHYDRO-3-OXO-,ETH, GLXC-07958, HMS3429M14, HY-A0270, Tox21_113073, BDBM50225701, EBC-26728, EX-A10465, AKOS001675735, Tox21_113073_1, AC-4261, DB01231, K-478-A, NCGC00016624-01, NCGC00016624-02, NCGC00016624-05, AS-88604, DA-62864, CAS-3254-89-5, Benzhydrol, .alpha.-(3-piperidinopropyl)-, CS-0017619, NS00040512, .alpha.,.alpha.-Diphenyl-1-piperidinebutanol, 1,1-Diphenyl-4-(1-piperidinyl)-1-butanol #, C06961, D03858, H52258, EN300-22536348, Q5279734, BRD-K01663662-003-03-8, BRD-K01663662-003-20-2, InChI=1/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
Theoretical properties:
molecular_formula: C21H27NO
molecular_weight: 309.4 g/mol
exact_mass: 309.209264485 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 6
heavy_atom_count: 23
topological_polar_surface_area: 23.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: NEEDLES FROM PETROLEUM ETHER
color: NEEDLES FROM PETROLEUM ETHER
odor: ODORLESS
melting_point: 212-214
solubility: CRYSTALS FROM CHLOROFORM + ETHYL ACETATE; FREELY SOL IN METHANOL; SOL IN WATER & CHLOROFORM; PRACTICALLY INSOL IN ETHER, BENZENE, & PETROLEUM ETHER /HCL/
Descriptions:
pubchem: Diphenidol is a tertiary alcohol that is butan-1-ol substituted by two phenyl groups at position 1 and a piperidin-1-yl group at position 4. It has a role as an antiemetic. It is a member of benzenes, a member of piperidines and a tertiary alcohol.
chebi: A tertiary alcohol that is butan-1-ol substituted by two phenyl groups at position 1 and a piperidin-1-yl group at position 4.
chembl: DIPHENIDOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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.