P-methyl-1,2,3,6-tetrahydropyridin-1-ium-4-phosphinate hydrate

• ChemBase ID: 132738
• Molecular Formular: C6H14NO3P
• Molecular Mass: 179.154021
• Monoisotopic Mass: 179.07112994
• SMILES: CP(=O)(C1=CC[NH2+]CC1)[O-].O
• Canonical SMILES: [O-]P(=O)(C1=CC[NH2+]CC1)C.O
• InChI: InChI=1S/C6H12NO2P.H2O/c1-10(8,9)6-2-4-7-5-3-6;/h2,7H,3-5H2,1H3,(H,8,9);1H2
• InChIKey: GXVWAQPRAQORGS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: P-methyl-1,2,3,6-tetrahydropyridin-1-ium-4-phosphinate hydrate
• IUPAC Traditional name: P-methyl-1,2,3,6-tetrahydropyridin-1-ium-4-phosphinate hydrate
• Synonyms: TPMPA hydrate; (1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid hydrate

Database IDs

• CAS Number: 182485-36-5(anhydrous)
• PubChem SID: 162227015; 24278172
• PubChem CID: 16220005

CALCULATED PROPERTIES

• Acid pKa: 3.5317206
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -3.3191957
• LogD (pH = 7.4): -3.3158388
• Log P: -3.3151975
• Molar Refractivity: 52.6825 cm^3
• Polarizability: 15.928932 Å^3
• Polar Surface Area: 56.74 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: insoluble; H2O: soluble16 mg/mL
• Apperance: white to off-white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97% (NMR)

DETAILS

Sigma Aldrich - T200

Legal Information
Sold in the USA under exclusive license from the University of California.
Biochem/physiol Actions
TPMPA is a hybrid of isoguvacine and 3-APMPA designed to retain affinity for GABAC receptors but not to interact with GABAA or GABAB receptors. Electrical assays show that TPMPA is a competitive antagonist of cloned human mu 1 GABAC receptors expressed in Xenopus laevis oocytes (Kb approx. 2 μM). TPMPA is >100-fold weaker as an inhibitor of rat brain GABAA receptors expressed in oocytes (Kb approx. 320 μM) and has only weak agonist activity on GABAB receptors assayed in rat hippocampal slices (EC50 approx. 500 μM). TPMPA may be used to investigate GABAC receptor function in the outer retina and in any other areas of the nervous system in which these types of receptor are present.