T200
(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid hydrate
≥97% (HPLC), solid
Synonyme(s) :
TPMPA hydrate
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About This Item
Formule empirique (notation de Hill):
C6H12NO2P · xH2O
Numéro CAS:
Poids moléculaire :
161.14 (anhydrous basis)
Code UNSPSC :
12352106
ID de substance PubChem :
Nomenclature NACRES :
NA.77
Produits recommandés
Niveau de qualité
Pureté
≥97% (HPLC)
Forme
solid
Couleur
white to off-white
Solubilité
H2O: 16 mg/mL
DMSO: insoluble
Chaîne SMILES
[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
Clé InChI
GXVWAQPRAQORGS-UHFFFAOYSA-N
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.
TPMA has been used as a GABAC receptor antagonist to study the role of inner retinal inhibition in midget ganglion cells. TPMPA has also been used to study the role of GABAC receptor antagonists in suppressing orientation selectivity in ganglion cells.
Actions biochimiques/physiologiques
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.
Caractéristiques et avantages
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.
Notes préparatoires
(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid (TPMPA) hydrate is soluble in water at 16 mg/ml, but is insoluble in DMSO.
Informations légales
Sold in the USA under exclusive license from the University of California.
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Équipement de protection individuelle
Eyeshields, Gloves, type N95 (US)
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Les clients ont également consulté
G A Johnston
Trends in pharmacological sciences, 17(9), 319-323 (1996-09-01)
The inhibitory neurotransmitter, GABA, activates a variety of receptors in all areas of the CNS. Two major subtypes of GABA receptors are well known: (1) GABAA receptors are ligand-gated Cl- channels that consist of a heteromeric mixture of protein subunits
Montserrat Samsó
European journal of translational myology, 25(1), 4840-4840 (2016-02-26)
Excitation contraction coupling, the rapid and massive Ca(2+) release under control of an action potential that triggers muscle contraction, takes places at specialized regions of the cell called triad junctions. There, a highly ordered supramolecular complex between the dihydropyridine receptor
Sowmya Venkataramani et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(46), 15664-15676 (2010-11-19)
Cells sensitive to the orientation of edges are ubiquitous in visual systems, and have been described in the vertebrate retina, yet the synaptic mechanisms that generate orientation selectivity in the retina are largely unknown. Here, we analyze the synaptic mechanisms
M Chebib et al.
British journal of pharmacology, 122(8), 1551-1560 (1998-01-10)
1. gamma-Aminobutyric acid (GABA) and trans-4-aminocrotonic acid (TACA) have been shown to activate GABAC receptors. In this study, a range of C2, C3, C4 and N-substituted GABA and TACA analogues were examined for activity at GABAC receptors. 2. The effects
The first selective antagonist for a GABAC receptor.
Murata, Y., et al.
Bioorganic & Medicinal Chemistry Letters, 6, 2073-2076 (1996)
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