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Details

Stereochemistry ACHIRAL
Molecular Formula C20H24N.CH3O4S
Molecular Weight 389.508
Optical Activity NONE
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHEMANIL METHYLSULFATE

SMILES

COS([O-])(=O)=O.C[N+]1(C)CCC(CC1)=C(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=BREMLQBSKCSNNH-UHFFFAOYSA-M
InChI=1S/C20H24N.CH4O4S/c1-21(2)15-13-19(14-16-21)20(17-9-5-3-6-10-17)18-11-7-4-8-12-18;1-5-6(2,3)4/h3-12H,13-16H2,1-2H3;1H3,(H,2,3,4)/q+1;/p-1

HIDE SMILES / InChI
Molecular Formula CH3O4S
Molecular Weight 111.097
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C20H24N
Molecular Weight 278.4113
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity NONE

Description

Diphemanil methylsulfate (Prantal), a quarternary amine, is a highly specific parasympathetic blocking agent.

Originator

Schering
47
Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/diphemanil-methylsulfate.html

Approval Year

1951
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
PRANTAL

Approved Use

Diphemanil Methylsulfate is used for Peptic ulcer, Gastric hyperacidity, Hypermotility in gastritis, Pylorospasm, Hyperhidrosis and other conditions.
Primary
Approved
8583
PRANTAL

Approved Use

Diphemanil Methylsulfate is used for Peptic ulcer, Gastric hyperacidity, Hypermotility in gastritis, Pylorospasm, Hyperhidrosis and other conditions.
Primary
Approved
8583
PRANTAL

Approved Use

Diphemanil Methylsulfate is used for Peptic ulcer, Gastric hyperacidity, Hypermotility in gastritis, Pylorospasm, Hyperhidrosis and other conditions.
Primary
Approved
8583
PRANTAL

Approved Use

Diphemanil Methylsulfate is used for Peptic ulcer, Gastric hyperacidity, Hypermotility in gastritis, Pylorospasm, Hyperhidrosis and other conditions.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
47.9 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1623915/
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHEMANIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
433 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1623915/
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHEMANIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.35 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1623915/
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHEMANIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
8.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8087216/
3 mg/kg single, oral
dose: 3 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHEMANIL plasma
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
2 mg single, respiratory
Highest studied dose
Dose: 2 mg
Route: respiratory
Route: single
Dose: 2 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6696291
unhealthy, 25 years (range: 19-40 years)
Health Status: unhealthy
Age Group: 25 years (range: 19-40 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6696291
Sources:
https://pubmed.ncbi.nlm.nih.gov/6696291
2 % single, topical
Highest studied dose
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://pubmed.ncbi.nlm.nih.gov/2190054
unhealthy, 27-66 years
Health Status: unhealthy
Age Group: 27-66 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2190054
Other AEs: Dry mouth...
Other AEs:
Dry mouth (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2190054
250 mg single, oral
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1623915
healthy, 30.8 years (range: 26 -42 years)
Health Status: healthy
Age Group: 30.8 years (range: 26 -42 years)
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/1623915
Other AEs: Dry mouth, Headache...
Other AEs:
Dry mouth (1 patient)
Headache (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/1623915
AEs

AEs

AESignificanceDosePopulation
Dry mouth 2 patients
2 % single, topical
Highest studied dose
Dose: 2 %
Route: topical
Route: single
Dose: 2 %
Sources:
https://pubmed.ncbi.nlm.nih.gov/2190054
unhealthy, 27-66 years
Health Status: unhealthy
Age Group: 27-66 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/2190054
Dry mouth 1 patient
250 mg single, oral
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1623915
healthy, 30.8 years (range: 26 -42 years)
Health Status: healthy
Age Group: 30.8 years (range: 26 -42 years)
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/1623915
Headache 1 patient
250 mg single, oral
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1623915
healthy, 30.8 years (range: 26 -42 years)
Health Status: healthy
Age Group: 30.8 years (range: 26 -42 years)
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/1623915
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00ECU3
ABI Chem
AC1L1LUR
AbovChem LLC
HY-16171
AK Scientific
2381AH
ApexBio Technology
A8414
AstaTech
C75961
BLD Pharm
BD125810
BOC Sciences
62-97-5
Chem Scene
CS-0906
Chemieliva Pharmaceutical Co., Ltd
PBCM1197720
ChemShuttle
141690
ChemTik
CTK5J1974
Compound Cloud
6126
Compound Cloud
6127
eMolecules
33507697
eNovation Chemicals
D389129
KeyOrganics
AS-67309
Lab Network
LN01285312
mcule
MCULE-3561653202
mcule
MCULE-8923880467
MedChem Express
HY-16171
MolPort
MolPort-003-666-719
MuseChem
A000461
Ryan Scientific
Melatonine
Selleck Chemicals
S4034
TargetMol
T0594
ZINC
ZINC000001482039
http://zinc15.docking.org/substances/ZINC000001482039
PubMed

PubMed

TitleDatePubMed
Treatment of Frey's syndrome with topical 2% diphemanil methylsulfate (Prantal): a double-blind evaluation of 15 patients.
1990-06
Effect of inhaled diphemanil methylsulfate, a parasympatholytic agent, on histamine induced bronchoconstriction in asymptomatic asthmatics.
1984-01
Prantal in dermatology.
1952-05
Prantal in the treatment of hyperhidrosis.
1951-10
Patents

Patents

20050002865
228
US2739968
2

Sample Use Guides

In Vivo Use Guide
Diphenylmethane methylsulfate was prescribed for the treatment of hyperhidrosis in a divided daily dosage of 200—400 mg. Fifteen patients with severe gustatory sweating after total parotidectomy and facial nerve preservation were alternatively treated with topically applied placebo and topically applied 2% diphemanil methylsulfate. 2 mg dose of diphemanil, administered by oral inhalation 20 minutes before histamine challenge, is ineffective in protecting against induced bronchospasm in asymptomatic adult asthmatics.
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:15:59 GMT 2025
Edited
by admin
on Mon Mar 31 18:15:59 GMT 2025
Record UNII
W2ZG23MGYI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPHEMANIL METILSULFATE
INN   MART.   WHO-DD  
INN  
Preferred Name English
DIPHEMANIL METHYLSULFATE
GREEN BOOK   MI   ORANGE BOOK  
Common Name English
NSC-41725
Code English
PIPERIDINIUM, 4-(DIPHENYLMETHYLENE)-1,1-DIMETHYL-, METHYL SULFATE
Common Name English
DIPHEMANIL METHYLSULFATE [GREEN BOOK]
Common Name English
4-(DIPHENYLMETHYLENE)-1,1-DIMETHYLPIPERIDINIUM METHYL SULPHATE
Systematic Name English
DIPHEMANIL METHYLSULPHATE
Common Name English
DIPHEMANIL METHYLSULFATE [ORANGE BOOK]
Common Name English
Diphemanil metilsulfate [WHO-DD]
Common Name English
4-DIPHENYLMETHYLENE-1,1-DIMETHYL-PIPERIDINIUM METHYLSULFATE
Systematic Name English
PIPERIDINIUM, 4-(DIPHENYLMETHYLENE)-1,1-DIMETHYL-, METHYL SULPHATE
Common Name English
PRANTAL
Code English
DIPHEMANIL METHYLSULFATE [MI]
Common Name English
4-(Diphenylmethylene)-1,1-dimethylpiperidinium methyl sulfate
Systematic Name English
DIPHEMANIL METILSULFATE [MART.]
Common Name English
diphemanil metilsulfate [INN]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 310.201
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
NCI_THESAURUS C29704
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
Code System Code Type Description
CAS
62-97-5
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
WIKIPEDIA
DIPHEMANIL METILSULFATE
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
NSC
41725
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
EVMPD
SUB07208MIG
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
FDA UNII
W2ZG23MGYI
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
EPA CompTox
DTXSID9022948
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
PUBCHEM
6126
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
CHEBI
59782
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
NCI_THESAURUS
C65419
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
SMS_ID
100000082877
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201340
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
DRUG BANK
DB00729
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
MESH
C028209
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
INN
342
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
MERCK INDEX
m4606
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY Merck Index
RXCUI
23364
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
200-552-4
Created by admin on Mon Mar 31 18:15:59 GMT 2025 , Edited by admin on Mon Mar 31 18:15:59 GMT 2025
PRIMARY
Related Record Type Details
Structure of Methyl sulfate
PARENT -> SALT/SOLVATE
Structure of DIPHEMANIL
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DIPHEMANIL
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