U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H12NO2P
Molecular Weight 161.1387
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TPMPA

SMILES

CP(O)(=O)C1=CCNCC1

InChI

InChIKey=MFUKVPOVVKKLRQ-UHFFFAOYSA-N
InChI=1S/C6H12NO2P/c1-10(8,9)6-2-4-7-5-3-6/h2,7H,3-5H2,1H3,(H,8,9)

HIDE SMILES / InChI
Molecular Formula C6H12NO2P
Molecular Weight 161.1387
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

(1,2,5,6-tetrahydropyridine-4-yl)methylphosphinic acid (TPMPA) is a competitive antagonist of gamma-aminobutyric acid (GABA)C receptors.

CNS Activity

CNS Active
3913
Curator's Comment: Centrally administered TPMPA is CNS active in animals. However, TPMPA does not cross the blood-brain barrier because no central effects upon systemic administration have been reported to date. No human data available.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Design and in vitro pharmacology of a selective gamma-aminobutyric acidC receptor antagonist.
1996 Oct
Patents

Patents

US5627169A
1

Sample Use Guides

In Vivo Use Guide
TPMPA (100 μmol/rat) was administered intracerebroventricularly (ICV)
Route of Administration: Other
In Vitro Use Guide
Muscimol (100 μM) caused a transient increase of the [Ca(2+)]i in RPE cells regardless of whether Ca(2+) was added to the buffer. Muscimol-induced increases in the [Ca(2+)]i were inhibited by pretreatment with picrotoxin (300 μM) or TPMPA (500 μM).
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:47:01 UTC 2023
Edited
by admin
on Sat Dec 16 10:47:01 UTC 2023
Record UNII
TR7I0800L2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TPMPA
MI  
Common Name English
TPMPA [MI]
Common Name English
P-METHYL-P-(1,2,3,6-TETRAHYDRO-4-PYRIDINYL)PHOSPHINIC ACID
Systematic Name English
PHOSPHINIC ACID, P-METHYL-P-(1,2,3,6-TETRAHYDRO-4-PYRIDINYL)-
Systematic Name English
Code System Code Type Description
WIKIPEDIA
TPMPA
Created by admin on Sat Dec 16 10:47:01 UTC 2023 , Edited by admin on Sat Dec 16 10:47:01 UTC 2023
PRIMARY
CAS
182485-36-5
Created by admin on Sat Dec 16 10:47:01 UTC 2023 , Edited by admin on Sat Dec 16 10:47:01 UTC 2023
PRIMARY
MERCK INDEX
m10992
Created by admin on Sat Dec 16 10:47:01 UTC 2023 , Edited by admin on Sat Dec 16 10:47:01 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID801017153
Created by admin on Sat Dec 16 10:47:01 UTC 2023 , Edited by admin on Sat Dec 16 10:47:01 UTC 2023
PRIMARY
FDA UNII
TR7I0800L2
Created by admin on Sat Dec 16 10:47:01 UTC 2023 , Edited by admin on Sat Dec 16 10:47:01 UTC 2023
PRIMARY
PUBCHEM
5520
Created by admin on Sat Dec 16 10:47:01 UTC 2023 , Edited by admin on Sat Dec 16 10:47:01 UTC 2023
PRIMARY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966