ZAPA sulfateAgonist at 'low affinity' GABAA receptor. More potent than GABA/muscimol CAS# 371962-01-5 |
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Chemical structure
3D structure
| Cas No. | 371962-01-5 | SDF | Download SDF |
| PubChem ID | 90479730 | Appearance | Powder |
| Formula | C4H8N2O6S2 | M.Wt | 244.24 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 10 mM in water | ||
| Chemical Name | (Z)-3-carbamimidoylsulfanylprop-2-enoic acid;sulfuric acid | ||
| SMILES | C(=CSC(=N)N)C(=O)O.OS(=O)(=O)O | ||
| Standard InChIKey | UWVNHPNVOMFDHW-ODZAUARKSA-N | ||
| Standard InChI | InChI=1S/C4H6N2O2S.H2O4S/c5-4(6)9-2-1-3(7)8;1-5(2,3)4/h1-2H,(H3,5,6)(H,7,8);(H2,1,2,3,4)/b2-1-; | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | More potent than either GABA or muscimol as an agonist at low affinity GABAA receptors and is thus a useful ligand to investigate GABA receptors linked to benzodiazepine receptors. Also a GABAA-ρ receptor antagonist. |
ZAPA sulfate Dilution Calculator
ZAPA sulfate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.0943 mL | 20.4717 mL | 40.9433 mL | 81.8867 mL | 102.3583 mL |
| 5 mM | 0.8189 mL | 4.0943 mL | 8.1887 mL | 16.3773 mL | 20.4717 mL |
| 10 mM | 0.4094 mL | 2.0472 mL | 4.0943 mL | 8.1887 mL | 10.2358 mL |
| 50 mM | 0.0819 mL | 0.4094 mL | 0.8189 mL | 1.6377 mL | 2.0472 mL |
| 100 mM | 0.0409 mL | 0.2047 mL | 0.4094 mL | 0.8189 mL | 1.0236 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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GABAc receptors: relatively simple transmitter -gated ion channels?[Pubmed:8885697]
Trends Pharmacol Sci. 1996 Sep;17(9):319-23.
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 forming a pentameric structure, and (2) GABAB receptors couple to Ca2+ and K+ channels via G proteins and second messengers. Here, Graham Johnston discusses evidence for a third major subclass of GABA receptors. GABAC receptors appear to be relatively simple ligand-gated Cl- channels with a distinctive pharmacology, in that they are not blocked by bicuculline and not modulated by barbiturates, benzodiazepines or neuroactive steroids. Compared with GABAA receptors, GABAC receptors are activated at lower concentrations of GABA and are less liable to desensitization. In addition, their channels open for a longer time. The pharmacology of these novel subtypes of GABA receptors may yield important therapeutic agents.
ZAPA, (Z)-3-[(aminoiminomethyl)thio]-2-propenoic acid hydrochloride, a potent agonist at GABA-receptors on the Ascaris muscle cell.[Pubmed:2851353]
Br J Pharmacol. 1988 Sep;95(1):3-5.
This study is the first report of a compound which is equal in efficacy to gamma-aminobutyric acid (GABA) at the nematode Ascaris muscle GABA-receptor. The GABA-receptor at the Ascaris muscle cell which mediates a membrane hyperpolarization and muscle relaxation has eluded classification. The structure-activity profile of this receptor is not typical of GABAA or GABAB-receptors. Here we report that the isothiouronium compound ZAPA is as potent as GABA at this receptor. This finding has important implications for the characterization of the Ascaris GABA-receptor and the design of novel anthelmintics.
Isothiouronium compounds as gamma-aminobutyric acid agonists.[Pubmed:3015310]
Br J Pharmacol. 1986 Jun;88(2):379-87.
Analogues of gamma-aminobutyric acid (GABA) incorporating an isothiouronium salt as a replacement for a protonated amino functional group have been investigated for activity on: GABA receptors in the guinea-pig ileum; [3H]-GABA and [3H]-diazepam binding to rat brain membranes; and GABA uptake and transamination. For the homologous series of omega-isothiouronium alkanoic acids, maximum GABA-mimetic activity was found at 3-[(aminoiminomethyl)thio]propanoic acid. Introduction of unsaturation into this compound gave two isomeric conformationally restricted analogues. The trans isomer was inactive at GABA receptors while the cis compound ((Z)-3-[(aminoiminomethyl)thio]prop-2-enoic acid (ZAPA)) was more potent than muscimol and GABA as a GABA agonist with respect to low affinity GABA receptor sites. Both isomers were moderately potent at inhibiting the uptake of [3H]-GABA into rat brain slices. Comparison of possible conformations of the two unsaturated isomers by interactive computer graphics modelling and comparison with muscimol has led to a plausible active conformation of ZAPA, which may be a selective and potent agonist for low affinity GABA binding sites.
