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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23NO.C7H7ClN4O2
Molecular Weight 496.001
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPRINHYDRINATE

SMILES

CN1C2=C(NC(Cl)=N2)C(=O)N(C)C1=O.CN3CCC(CC3)OC(C4=CC=CC=C4)C5=CC=CC=C5

InChI

InChIKey=JSNIFGPPGAINSG-UHFFFAOYSA-N
InChI=1S/C19H23NO.C7H7ClN4O2/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17;1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h2-11,18-19H,12-15H2,1H3;1-2H3,(H,9,10)

HIDE SMILES / InChI
Molecular Formula C19H23NO
Molecular Weight 281.392
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C7H7ClN4O2
Molecular Weight 214.609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/14238605 | https://www.ncbi.nlm.nih.gov/pubmed/14238604

Piprinhydrinate is compositon of Diphenylpyraline and 8-chloroteophylline. 8-Chlorotheophylline is a stimulant drug of the xanthine chemical class, with physiological effects similar to caffeine. Diphenylpyraline is an antihistamine that prevents, but does not reverse, responses mediated by histamine alone. Diphenylpyraline antagonizes most of the pharmacological effects of histamine, including urticaria and pruritus. Also, diphenylpyraline may exhibit anticholinergic actions (as do most of the antihistamines) and may thus provide a drying effect on the nasal mucosa. 8-Chlorotheophylline main use is in combination with Diphenylpyraline or diphenhydramine in the antiemetic Piprinhydrinate and dimenhydrinate. Diphenylpyraline (or diphenhydramine) reduces nausea but causes drowsiness, and the stimulant properties of 8-Chlorotheophylline help ward off that side-effect.

CNS Activity

Originator

Neuhoff, E.W.|Auterhoff, H.
1
Sources: Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, Volume 288, Pages 400-7, Journal, 1955

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 4.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[ON THE PRENATAL TOXICITY OF DIPHENYLPYRALINE 8-CHLOROTHEOPHYLLINATE WITH REFERENCE TO EXPERIENCES WITH THALIDOMIDE AND CAFFEINE].
1964-05
Patents

Patents

WO9800168
1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Brain tissue was obtained at autopsy on 18 Japanese patients with chronic schizophrenia. The brain tissues were weighed, homogenized and centrifuged. The specific 3H-mepyramine binding to the brain tissues reached equilibrium values within 20 min after incubation at 25°C. Inhibition of the specific component of the 3H-mepyramine binding by Diphenylpyraline was then studied. The H1 antagonist diphenylpyraline (Ki=4.1nM) was potent competitors for the specific binding of 3H-mepyramine.
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:52:18 GMT 2025
Edited
by admin
on Wed Apr 02 08:52:18 GMT 2025
Record UNII
SI78RFJ7XI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPRINHYDRINATE
INN   MART.   WHO-DD  
INN  
Official Name English
DIPHENYLPYRALINE 8-CHLOROTHEOPHYLLINATE
MI  
Preferred Name English
DIPHENYLPYRALINE TEOCLATE [JAN]
Common Name English
Piprinhydrinate [WHO-DD]
Common Name English
PIPRINHYDRINATE [MART.]
Common Name English
DIPHENYLPYRALINE 8-CHLOROTHEOPHYLLINATE [MI]
Common Name English
piprinhydrinate [INN]
Common Name English
DIPHENYLPYRALINE-8-CHLOROTHEOPHYLLINATE
Common Name English
DIPHENYLPYRALINE TEOCLATE
JAN  
Common Name English
4-DIPHENYLMETHOXY-1-METHYLPIPERIDINE COMPOUND OF 8-CHLOROTHEOPHYLLINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
Code System Code Type Description
SMS_ID
100000082219
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
MERCK INDEX
m4640
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY Merck Index
INN
830
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
EVMPD
SUB09886MIG
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
NCI_THESAURUS
C66408
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
FDA UNII
SI78RFJ7XI
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
EPA CompTox
DTXSID80209413
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
CAS
606-90-6
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
ChEMBL
CHEMBL1492
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
ECHA (EC/EINECS)
210-128-0
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
PUBCHEM
71640
Created by admin on Wed Apr 02 08:52:18 GMT 2025 , Edited by admin on Wed Apr 02 08:52:18 GMT 2025
PRIMARY
Related Record Type Details
Structure of 8-Chlorotheophylline
PARENT -> SALT/SOLVATE
Structure of DIPHENYLPYRALINE
PARENT -> SALT/SOLVATE
NIH
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