Basic information
- CAS
972-02-1- Standard SMILES
OC(CCCN1CCCCC1)(c1ccccc1)c1ccccc1- InChIKey
OGAKLTJNUQRZJU-UHFFFAOYSA-N- Molecular formula
- C21H27NO
- Average molar mass
- 309.4 g/mol
- Monoisotopic mass
- 309.20926449
Overview
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.
Names & identifiers
- Preferred name
- Diphenidol
- IUPAC
- 1,1-diphenyl-4-piperidin-1-ylbutan-1-ol
- English name
- Difenidol
- Molecular formula
- C21H27NO
- Molecular weight
- 309.45
Names & synonyms
DIPHENIDOLDifenidol972-02-1NometicAvomolDifenidoloDifenidolum1,1-Diphenyl-4-(piperidin-1-yl)butan-1-olalpha,alpha-Diphenyl-1-piperidinebutanolDiphenyl(3-(1-piperidyl)propyl)carbinolSKF 478SK&F 478
Show more names
VontrolCephadolSK&F No. 478-ADifenidol USP/EP/BP1-Piperidinebutanol, α,α-diphenyl-
SK&F-478SK-478DTXSID3022950NQO8R319LYCHEBI:4638Benzhydrol, alpha-(3-piperidinopropyl)-1-Piperidinebutanol, alpha,alpha-diphenyl-DTXCID502950
Database identifiers
- CAS
972-02-1- PubChem CID
- 3055
- DTXSID
DTXSID3022950- ChEMBL
CHEMBL936- ChEBI
CHEBI:4638- UNII
- NQO8R319LY
- EC Number
- 213-540-9
- Nikkaji
- J7.202H
Properties
Computed structural properties
- XLogP
- 4.2
- Topological polar surface area
- 23.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 6
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 307
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP4.3
OdorODORLESS
TasteSLIGHTLY BITTER TASTE
Color/Form
NEEDLES FROM PETROLEUM ETHER
WHITE CRYSTALLINE POWDER
Solubility
CRYSTALS FROM CHLOROFORM + ETHYL ACETATE; FREELY SOL IN METHANOL; SOL IN WATER & CHLOROFORM; PRACTICALLY INSOL IN ETHER, BENZENE, & PETROLEUM ETHER /HCL/
FREELY SOL IN CHLOROFORM, ETHER & CYCLOHEXANE; SPARINGLY SOL IN ALC; INSOL IN WATER
5.87e-03 g/L
Melting Point
212-214
104-105 °C
Physical DescriptionSolid
Stability/Shelf LifeSTABLE IN LIGHT & AIR
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Human Toxicity Excerpts
...AUDITORY & VISUAL HALLUCINATIONS, DISORIENTATION, & CONFUSION HAVE BEEN REPORTED. OTHER UNTOWARD EFFECTS SUCH AS DROWSINESS, DRY MOUTH, DIZZINESS, SKIN RASH, HEARTBURN, HEADACHE, NAUSEA...MALAISE, ETC HAVE BEEN INFREQUENT & MINOR IN NATURE.
Non-Human Toxicity ExcerptsANIMAL EXPERIMENTS HAVE REVEALED NO EVIDENCE OF TERATOGENIC EFFECTS.
Non-Human Toxicity Values
LD50 MICE ORAL 430 MG/KG /HCL/
LD50 MICE INTRAPERITONEAL 105 MG/KG /HCL/
LD50 MICE INTRAVENOUS 37 MG/KG /HCL/
LD50 RATS ORAL 515 MG/KG /HCL/
For more Non-Human Toxicity Values (Complete) data for DIPHENIDOL (6 total), please visit the HSDB record page.
Safety data
- Toxicity
- LD50 s.c. in rats: 50 mg/kg (Goldenthal)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
- Hazardous Substances Data
- 972-02-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
PharmacodynamicsDiphenidol is used for control of nausea and vomiting. It has an antivertigo effect on the vestibular apparatus, inhibiting the chemoreceptor trigger zone to control nausea and vomiting, thus preventing motion sickness.
Mechanism of Action
The mechanism by which diphenidol exerts its antiemetic and antivertigo effects is not precisely known. It is thought to diminish vestibular stimulation and depress labyrinthine function and as an antimuscarinic agent. An action on the medullary chemoreceptive trigger zone may also be involved in the antiemetic effect. Diphenidol has no significant sedative, tranquilizing, or antihistaminic action. It has a weak peripheral anticholinergic effect.
EXPTL, IT HAS BEEN SHOWN TO EXHIBIT WEAK PARASYMPATHOLYTIC ACTIONS, BUT TO LACK SIGNIFICANT SEDATIVE, TRANQUILIZING, OR ANTIHISTAMINIC PROPERTIES.
.../DIPHENIDOL/ IS THOUGHT TO ACT UPON AURAL VESTIBULAR APPARATUS...
Biological Half-Life4 hours
Metabolism/MetabolitesIN DOGS & IN MAN, PRINCIPAL URINARY METABOLITE OF DIPHENIDOL...WAS N-(4,4-DIPHENYL-4-HYDROXYBUTYL)-DELTA-AMINOVALERIC ACID...(NOT LESS THAN 50% OF DOSE)... MINOR URINARY METABOLITES INCL A PHENOL...& A LACTAM...
FDA Pharmacological Classification
NQO8R319LY
DIPHENIDOL
Established Pharmacologic Class [EPC] - Antiemetic
Physiologic Effects [PE] - Emesis Suppression
Diphenidol is an Antiemetic. The physiologic effect of diphenidol is by means of Emesis Suppression.
MeSH Pharmacological ClassificationDrugs used to prevent NAUSEA or VOMITING.
Absorption, Distribution and ExcretionWell absorbed from gastrointestinal tract following oral administration.
Cellular LocationsMembrane
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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