CAS Number102-02-3
SynonymsN-Phenyliminodicarbonimidic Diamide; Phenylbiguanide; MFCD00179077; 1-(diaminomethylidene)-2-phenylguanidine; EINECS 202-998-5
Molecular FormulaC6H5NHC(=NH)NHC(=NH)NH2
Molecular Weight177.21
Purity98%
Density1.33g/cm3
Boiling Point388.4ºC at 760mmHg
Melting Point135-142 °C (lit.)
Appearancesolid
EINECS202-998-5
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 102-02-3 |
| Catalog No. | 2A-9008668 |
| Chinese Name | 苯基双胍 |
| Synonyms | N-Phenyliminodicarbonimidic Diamide; Phenylbiguanide; MFCD00179077; 1-(diaminomethylidene)-2-phenylguanidine; EINECS 202-998-5 |
| Molecular Formula | C6H5NHC(=NH)NHC(=NH)NH2 |
| Molecular Weight | 177.21 |
| Purity | 98 |
| Density | 1.33g/cm3 |
| Boiling Point | 388.4ºC at 760mmHg |
| Melting Point | 135-142 °C (lit.) |
| Appearance | solid |
| Storage Condition | Room Temperature |
| Application | Phenylbiguanide is a selective 5-HT3 receptor agonist with an EC50 of 3.0±0.1 μM. |
| EINECS | 202-998-5 |
| HTC | 2925.29.6000 |
| PubChem ID | 24850064 |
| MDL Number | MFCD00179077 |
| SMILES | NC(=N)\N=C(/N)Nc1ccccc1 |
| InChI | 1S/C8H11N5/c9-7(10)13-8(11)12-6-4-2-1-3-5-6/h1-5H,(H6,9,10,11,12,13) |
| InChI Key | CUQCMXFWIMOWRP-UHFFFAOYSA-N |
| NACRES Code | NA.22 |
| UNSPSC | 12352100 |
| MSDS | msds/8668_1_102_02_3.pdf |
| Bioactivity | Phenylbiguanide is a 5-HT3 receptor selective agonist with an EC50 of 3.0±0.1 μM. Related Catalog Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor Research Areas >> Neurological Disease Target 5-HT3 Receptor:3 μM (EC50) In Vitro Phenylbiguanide (1-Phenylbiguanide) is a 5-HT3 receptor selective agonist with pEC50s of 5.57, 4.07, and 4.47 for r5-HT3A(b), h5-HT3A, m5-HT3A(b) , respectively[1]. The effect of Phenylbiguanide (1-Phenylbiguanide hydrochloride) in promoting the growth of the HT29 cell line is investigated. Phenylbiguanide causes a dose dependent proliferation of HT29 cells after 48 hours incubation. The maximum proliferation is at a 5HT concentration of 12.5 μM (P≤0.01). Phenylbiguanide significantly stimulates the growth of cells at concentrations of 3.125 μM (P≤0.05) and 6.25 μM (P≤0.01)[2]. In Vivo In anaesthetised mice, Phenylbiguanide (PBG), a drug that is known to stimulate cardiopulmonary afferent C-fibres,is injected into the right atrium of the heart and mapped c-Fos expression within specific regions of the central nervous system. Intraatrial injection of PBG produces a reflex cardiorespiratory response including a pronounced bradycardia and a respiratory depression[3]. Cell Assay HT29 cells are washed with Phosphate buffer saline (PBS) and harvested with a 0.5% trypsin solution at 50-60% confluency. Cells are then added to wells at a density of 104 cells/well in a 96-well plate to a final volume of 100 μL/well. After 24 hours of incubation at 37°C in a 5% CO2 atmosphere, the culture medium is replaced with 200 μL fresh culture medium containing 5HT hydrochloride, Phenylbiguanide hydrochloride at concentrations of: 3.125, 6.25, 12.5, 25, 50, and 100 µM . Cells cultured solely in media served as negative controls. After 48 hours of incubation at 37°C in a 5% CO2 atmosphere, the culture medium is removed and 8 µL MTT reagent (diluted in PBS at a concentration of 4 mg/mL) is added to 50 μL of fresh culture medium at a final concentration of 0.55 mg/mL. The optimum incubation period time is determined in a pilot study[2]. Animal Admin Mice[3] Adult male specified pathogen free (SPF) BALB/c mice (28-33 g; n=10) are used throughout this study. All mice have free access to water and food in a light (12: 12 h light/ dark cycle, lights on at 0700 h) and temperature-controlled (21-23°C) environment. Mice are randomly assigned to two treatment groups, 1) intra-atrial injection of 0.9% saline (controls, n=5) or 2) intra-atrial injection of vehicle containing Phenylbiguanide (n=5). For the PBGinjected group, mice are injected with an effective dose of Phenylbiguanide (1-1.5 μg in 10-15 μL saline) . This is repeated five times in total with each injection separated by 8-10 min. For control mice, each mouse receives five saline injections (10-15 μL each), also at 8-10 min intervals[3]. References [1]. Mair ID, et al. Pharmacological characterization of a rat 5-hydroxytryptamine type3 receptor subunit (r5-HT3A(b)) expressed in Xenopus laevis oocytes. Br J Pharmacol. 1998 Aug;124(8):1667-74. [2]. Ataee R, et al. Study of 5HT3 and HT4 receptor expression in HT29 cell line and human colon adenocarcinoma tissues. Arch Iran Med. 2010 Mar;13(2):120-5. [3]. de Vries A, et al. Characterisation of c-Fos expression in the central nervous system of mice following right atrialinjections of the 5-HT3 receptor agonist Phenylbiguanide. Auton Neurosci. 2005 Dec 30;123(1-2):62-75. Chemical & Physical Properties Density 1.33g/cm3 Boiling Point 388.4ºC at 760mmHg Melting Point 135-142 °C(lit.) Molecular Formula C8H11N5 Molecular Weight 177.20600 Flash Point 188.7ºC Exact Mass 177.10100 PSA 100.28000 LogP 1.88000 Vapour Pressure 3.08E-06mmHg at 25°C Index of Refraction 1.656 InChIKey CUQCMXFWIMOWRP-UHFFFAOYSA-N SMILES NC(N)=NC(N)=Nc1ccccc1 |
| Use of | Properties Articles31 Name phenyl biguanide Synonym More Synonyms Phenylbiguanide Biological Activity Related Catalog Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor Research Areas >> Neurological Disease 5-HT3 Receptor:3 μM (EC50) In Vivo In anaesthetised mice, Phenylbiguanide (PBG), a drug that is known to stimulate cardiopulmonary afferent C-fibres,is injected into the right atrium of the heart and mapped c-Fos expression within specific regions of the central nervous system. Intraatrial injection of PBG produces a reflex cardiorespiratory response including a pronounced bradycardia and a respiratory depression[3]. References [1]. Mair ID, et al. Pharmacological characterization of a rat 5-hydroxytryptamine type3 receptor subunit (r5-HT3A(b)) expressed in Xenopus laevis oocytes. Br J Pharmacol. 1998 Aug;124(8):1667-74. [3]. de Vries A, et al. Characterisation of c-Fos expression in the central nervous system of mice following right atrialinjections of the 5-HT3 receptor agonist Phenylbiguanide. Auton Neurosci. 2005 Dec 30;123(1-2):62-75. Chemical & Physical Properties Molecular Formula C8H11N5 Exact Mass 177.10100 PSA 100.28000 LogP 1.88000 Index of Refraction 1.656 InChIKey CUQCMXFWIMOWRP-UHFFFAOYSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified |
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