TPMPA
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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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGamma-aminobutyric acid receptor subunit rho-1 antagonistHumans UGamma-aminobutyric acid receptor subunit rho-2 antagonistHumans UGamma-aminobutyric acid receptor subunit rho-3 antagonistHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- 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]
- 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]
- 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]
- 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]
- External Links
- ChemSpider
- 5319
- ChEMBL
- CHEMBL397209
- ZINC
- ZINC000025720700
- PDBe Ligand
- VZA
- Wikipedia
- (1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic_acid
- PDB Entries
- 8oq7
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble to 100 mM https://documents.tocris.com/pdfs/tocris_msds/1040_sds.pdf?1644409107 - Predicted Properties
Property Value Source Water Solubility 27.2 mg/mL ALOGPS logP -0.53 ALOGPS logP -2.5 Chemaxon logS -0.77 ALOGPS pKa (Strongest Acidic) 3.53 Chemaxon pKa (Strongest Basic) 9.88 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 49.33 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 42.39 m3·mol-1 Chemaxon Polarizability 15.35 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0900000000-734803c5dad03d946841 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-1900000000-f1910d111c2f9d28da7e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-01oy-1900000000-c9f0071cec3b14a7616e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-9000000000-a684edc47b05d6ffb3a9 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0f89-9000000000-e118efc4d9b5625c6d9d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-9000000000-2fdeae2eced5cebd1a1e Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- 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
- 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
- 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
- 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