Physicochemical Properties
| Molecular Formula | C25H27CL2N3O2S |
| Molecular Weight | 504.471782922745 |
| Exact Mass | 503.12 |
| CAS # | 1781934-44-8 |
| Related CAS # | NPS ALX Compound 4a;299433-10-6 |
| PubChem CID | 56972226 |
| Appearance | Typically exists as solid at room temperature |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 33 |
| Complexity | 752 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | XQQYORJJFZQWNA-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C25H25N3O2S.2ClH/c29-31(30,25-9-3-6-19-5-1-2-8-23(19)25)28-14-12-20-10-11-21(17-24(20)28)27-16-15-26-13-4-7-22(26)18-27;;/h1-3,5-6,8-12,14,17,22H,4,7,13,15-16,18H2;2*1H |
| Chemical Name | 2-(1-naphthalen-1-ylsulfonylindol-6-yl)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine;dihydrochloride |
| Synonyms | NPS ALX Compound 4a diHCl; 299433-10-6; NPS ALX COMPOUND 4A DIHYDROCHLORIDE; 1781934-44-8; NPS ALX Compound 4a; 6-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1-(1-naphthalenylsulfonyl)-1H-indole dihydrochloride; NPS ALX Compound 4a 2HCl; NPSALXCompound4adihydrochloride; 2-(1-naphthalen-1-ylsulfonylindol-6-yl)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine;dihydrochloride; NPS ALX Compound 4a diHCl |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | 5-hydroxytryptamine6 (5-HT6) receptor; 5-HT6 Receptor (IC50 = 7.2 nM); 5-HT6 Receptor (Ki = 0.2 nM) |
| ln Vitro |
A novel series of 6-bicyclopiperazinyl-1-arylsulfonylindoles and 6-bicyclopiperidinyl-1-arylsulfonylindoles derivatives was synthesized and found to be potent and selective 5-HT6 receptor antagonists[1].
In the functional adenylyl cyclase assay, the most potent compound 4a/NPS ALX Compound 4a was found to be a competitive antagonist (IC50=7.2 nM) with good binding selectivity over a number of other key receptors [1]. In conclusion, a novel series of potent and selective 5-HT6 receptor antagonist has been developed. The compound 4a was the most potent compound from the series and has demonstrated good in vitro receptor selectivity thus making it a promising candidate for the possible treatment of schizophrenia, depression and memory dysfunction. Compound 4a is currently being further evaluated for its therapeutic potential. [1] |
| References |
[1]. 6-Bicyclopiperazinyl-1-arylsulfonylindoles and 6-bicyclopiperidinyl-1-arylsulfonylindolesderivatives as novel, potent, and selective 5-HT6 receptor antagonists. Bioorg Med Chem Lett. 2000 Aug 7;10(15):1719-21. |
| Additional Infomation |
The human 5-hydroxytryptamine6 (5-HT6) receptor, one of the most recently cloned serotonergic receptors, is a 440-amino acid polypeptide with seven transmembrane spanning domains typical of the G-protein-coupled receptors. It is one of the 14 receptors that mediate the effects of the neurotransmitter 5-hydroxytryptamine (5-HT, serotonin).1 Within the transmembrane region, the human 5-HT6 receptor shows about 30–40% homology to other human 5-HT receptors and is found to be positively coupled to adenylyl cyclase. The prominent localization of 5-HT6 receptor mRNA in the nucleus accumbens, striatum, olfactory tubercle, substantia nigra, and hippocampus of the brain,2 together with its high affinity for several therapeutically important antipsychotics and antidepressants suggest a possible role for this receptor in the treatment of schizophrenia and depression. In fact, the prototypic atypical antipsychotic agent clozapine exhibits greater affinity for the 5-HT6 receptor than for any other receptor subtype.[1] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9823 mL | 9.9114 mL | 19.8228 mL | |
| 5 mM | 0.3965 mL | 1.9823 mL | 3.9646 mL | |
| 10 mM | 0.1982 mL | 0.9911 mL | 1.9823 mL |