CAS 102-02-3|Phenylbiguanide
| Common Name | Phenylbiguanide | ||
|---|---|---|---|
| CAS Number | 102-02-3 | Molecular Weight | 177.20600 |
| Density | 1.33g/cm3 | Boiling Point | 388.4ºC at 760mmHg |
| Molecular Formula | C8H11N5 | Melting Point | 135-142 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 188.7ºC |
Names
| Name | phenyl biguanide |
|---|---|
| Synonym | More Synonyms |
Phenylbiguanide BiologicalActivity
| Description | 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 ReceptorSignaling Pathways >>Neuronal Signaling >>5-HT ReceptorResearch 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 500 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- MPHEAE Medicina et Pharmacologia Experimentalis. (Basel, Switzerland) V.12-17, 1965-67. For publisher information, see PHMGBN. Volume(issue)/page/year: 16,267,1967
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | DU2450000 |
Articles31
More Articles| Cardiovascular afferents cause the release of 5-HT in the nucleus tractus solitarii; this release is regulated by the low- (PMAT) not the high-affinity transporter (SERT). J. Physiol. 593(7) , 1715-29, (2015) The nucleus tractus solitarii (NTS) integrates inputs from cardiovascular afferents and thus is crucial for cardiovascular homeostasis. These afferents primarily release glutamate, although 5-HT has a... | |
| Microvascular dilation evoked by chemical stimulation of C-fibers in rats. J. Appl. Physiol. 118(1) , 55-60, (2015) Activation of pulmonary C-fibers can reflexively decrease heart rate, blood pressure, and peripheral vascular resistance. However, the effects of these afferents on microvascular tone remain incomplet... | |
| 5-HT1D receptor inhibits renal sympathetic neurotransmission by nitric oxide pathway in anesthetized rats. Vascul. Pharmacol. 72 , 172-80, (2015) Although serotonin has been shown to inhibit peripheral sympathetic outflow, serotonin regulation on renal sympathetic outflow has not yet been elucidated. This study investigated which 5-HT receptor ... |
Synonyms
| N-Phenyliminodicarbonimidic Diamide |
| Phenylbiguanide |
| MFCD00179077 |
| 1-(diaminomethylidene)-2-phenylguanidine |
| EINECS 202-998-5 |
