This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
TPMPA
DrugBank Accession Number
DB16754
Background

TPMPA ((1,2,5,6-tetrahydropyridine-4-yl)methylphosphinic acid) is a selective antagonist of GABAC receptors (also known as GABA-ρ or GABAA-ρ receptors).2 GABAC receptors are found primarily in the retina, although they may be present in other tissues, including the hippocampus, spinal cord, superior colliculus, pituitary and the gut.3,4 TPMPA is used as a pharmacological probe for the investigation of GABAC receptor function.4

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 161.141
Monoisotopic: 161.060565628
Chemical Formula
C6H12NO2P
Synonyms
  • (1,2,5,6-tetrahydropyridine-4-yl)methylphosphinic acid
  • P-Methyl-P-(1,2,3,6-tetrahydro-4-pyridinyl)phosphinic acid
  • Phosphinic acid, P-methyl-P-(1,2,3,6-tetrahydro-4-pyridinyl)-

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGamma-aminobutyric acid receptor subunit rho-1
antagonist
Humans
UGamma-aminobutyric acid receptor subunit rho-2
antagonist
Humans
UGamma-aminobutyric acid receptor subunit rho-3
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
TR7I0800L2
CAS number
182485-36-5
InChI Key
MFUKVPOVVKKLRQ-UHFFFAOYSA-N
InChI
InChI=1S/C6H12NO2P/c1-10(8,9)6-2-4-7-5-3-6/h2,7H,3-5H2,1H3,(H,8,9)
IUPAC Name
methyl(1,2,3,6-tetrahydropyridin-4-yl)phosphinic acid
SMILES
CP(O)(=O)C1=CCNCC1

References

Synthesis Reference

Ragozzino D, Woodward RM, Murata Y, Eusebi F, Overman LE, Miledi R: Design and in vitro pharmacology of a selective gamma-aminobutyric acidC receptor antagonist. Mol Pharmacol. 1996 Oct;50(4):1024-30.

General References
  1. Osolodkin DI, Chupakhin VI, Palyulin VA, Zefirov NS: Molecular modeling of ligand-receptor interactions in GABA C receptor. J Mol Graph Model. 2009 Apr;27(7):813-21. doi: 10.1016/j.jmgm.2008.12.004. Epub 2008 Dec 24. [Article]
  2. Ragozzino D, Woodward RM, Murata Y, Eusebi F, Overman LE, Miledi R: Design and in vitro pharmacology of a selective gamma-aminobutyric acidC receptor antagonist. Mol Pharmacol. 1996 Oct;50(4):1024-30. [Article]
  3. Naffaa MM, Hung S, Chebib M, Johnston GAR, Hanrahan JR: GABA-rho receptors: distinctive functions and molecular pharmacology. Br J Pharmacol. 2017 Jul;174(13):1881-1894. doi: 10.1111/bph.13768. Epub 2017 Apr 12. [Article]
  4. Johnston GA, Chebib M, Hanrahan JR, Mewett KN: Neurochemicals for the investigation of GABA(C) receptors. Neurochem Res. 2010 Dec;35(12):1970-7. doi: 10.1007/s11064-010-0271-7. Epub 2010 Oct 21. [Article]
ChemSpider
5319
ChEMBL
CHEMBL397209
ZINC
ZINC000025720700
Wikipedia
(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic_acid

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySoluble to 100 mMhttps://documents.tocris.com/pdfs/tocris_msds/1040_sds.pdf?1644409107
Predicted Properties
PropertyValueSource
Water Solubility27.2 mg/mLALOGPS
logP-0.53ALOGPS
logP-2.5Chemaxon
logS-0.77ALOGPS
pKa (Strongest Acidic)3.53Chemaxon
pKa (Strongest Basic)9.88Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area49.33 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity42.39 m3·mol-1Chemaxon
Polarizability15.35 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Gaba-a receptor activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-1 GABA...
Gene Name
GABRR1
Uniprot ID
P24046
Uniprot Name
Gamma-aminobutyric acid receptor subunit rho-1
Molecular Weight
55882.91 Da
References
  1. Osolodkin DI, Chupakhin VI, Palyulin VA, Zefirov NS: Molecular modeling of ligand-receptor interactions in GABA C receptor. J Mol Graph Model. 2009 Apr;27(7):813-21. doi: 10.1016/j.jmgm.2008.12.004. Epub 2008 Dec 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Gaba-a receptor activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA...
Gene Name
GABRR2
Uniprot ID
P28476
Uniprot Name
Gamma-aminobutyric acid receptor subunit rho-2
Molecular Weight
54150.41 Da
References
  1. Osolodkin DI, Chupakhin VI, Palyulin VA, Zefirov NS: Molecular modeling of ligand-receptor interactions in GABA C receptor. J Mol Graph Model. 2009 Apr;27(7):813-21. doi: 10.1016/j.jmgm.2008.12.004. Epub 2008 Dec 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Gaba-a receptor activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRR3
Uniprot ID
A8MPY1
Uniprot Name
Gamma-aminobutyric acid receptor subunit rho-3
Molecular Weight
54271.1 Da
References
  1. Osolodkin DI, Chupakhin VI, Palyulin VA, Zefirov NS: Molecular modeling of ligand-receptor interactions in GABA C receptor. J Mol Graph Model. 2009 Apr;27(7):813-21. doi: 10.1016/j.jmgm.2008.12.004. Epub 2008 Dec 24. [Article]

Drug created at February 08, 2022 21:17 / Updated at February 10, 2022 08:54