T200

(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid hydrate

≥97% (HPLC), solid

• Synonym(e): TPMPA hydrate
• Empirische Formel (Hill-System): C₆H₁₂NO₂P · xH₂O
• CAS-Nummer: 182485-36-5
• Molekulargewicht: 161.14 (anhydrous basis)
• UNSPSC Code: 12352106
• PubChem Substance ID: 24278172
• NACRES: NA.77
• Assay: ≥97% (HPLC)
• Form: solid

Eigenschaften

• Quality Segment: 100
• assay: ≥97% (HPLC)
• form: solid
• color: white to off-white
• solubility: H₂O: 16 mg/mL, DMSO: insoluble
• SMILES string: [H]O[H].CP([O-])(=O)C1=CC[NH2+]CC1
• InChI: 1S/C6H12NO2P.H2O/c1-10(8,9)6-2-4-7-5-3-6;/h2,7H,3-5H2,1H3,(H,8,9);1H2
• InChI key: GXVWAQPRAQORGS-UHFFFAOYSA-N

Beschreibung

Application

(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid hydrate has also been used as γ-aminobutyric acid C (GABAc) blocker in retinal ganglion cells.[1]

TPMA has been used as a GABA_C receptor antagonist to study the role of inner retinal inhibition in midget ganglion cells[2]. TPMPA has also been used to study the role of GABA_C receptor antagonists in suppressing orientation selectivity in ganglion cells[3].

Biochem/physiol Actions

TPMPA is a hybrid of isoguvacine and 3-APMPA designed to retain affinity for GABA_C receptors but not to interact with GABA_A or GABA_B receptors. Electrical assays show that TPMPA is a competitive antagonist of cloned human mu 1 GABA_C receptors expressed in Xenopus laevis oocytes (Kb approx. 2 μM). TPMPA is >100-fold weaker as an inhibitor of rat brain GABA_A receptors expressed in oocytes (Kb approx. 320 μM) and has only weak agonist activity on GABA_B receptors assayed in rat hippocampal slices (EC₅₀ approx. 500 μM). TPMP_A may be used to investigate GABA_C receptor function in the outer retina and in any other areas of the nervous system in which these types of receptor are present.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the GABAC Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid (TPMPA) hydrate is soluble in water at 16 mg/ml, but is insoluble in DMSO.

Legal Information

Sold in the USA under exclusive license from the University of California.

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)