Diphemanil MethylsulfateCAS# 62-97-5 |
- A-867744
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 62-97-5 | SDF | Download SDF |
| PubChem ID | 6126 | Appearance | Powder |
| Formula | C21H27NO4S | M.Wt | 389.51 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Diphemanil mesylate | ||
| Solubility | : 16.67 mg/mL (42.80 mM; Need ultrasonic) | ||
| Chemical Name | 4-benzhydrylidene-1,1-dimethylpiperidin-1-ium;methyl sulfate | ||
| SMILES | C[N+]1(CCC(=C(C2=CC=CC=C2)C3=CC=CC=C3)CC1)C.COS(=O)(=O)[O-] | ||
| Standard InChIKey | BREMLQBSKCSNNH-UHFFFAOYSA-M | ||
| Standard InChI | InChI=1S/C20H24N.CH4O4S/c1-21(2)15-13-19(14-16-21)20(17-9-5-3-6-10-17)18-11-7-4-8-12-18;1-5-6(2,3)4/h3-12H,13-16H2,1-2H3;1H3,(H,2,3,4)/q+1;/p-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 | Diphemanil methylsulfate is a quaternary ammonium anticholinergic. It binds muscarinic acetycholine receptors and thereby decreases secretory excretion of stomach acids as well as saliva and sweat.
IC50 value:
Target: mAChR
Diphemanil Methylsulfate exerts its action by primarily binding the muscarinic M3 receptor. M3 receptors are located in the smooth muscles of the blood vessels, as well as in the lungs. This means they cause vasodilation and bronchoconstriction. They are also in the smooth muscles of the gastrointestinal tract (GIT), which help in increasing intestinal motility and dilating sphincters. The M3 receptors are also located in many glands which help to stimulate secretion in salivary glands and other glands of the body. References: | |||||
Diphemanil Methylsulfate Dilution Calculator
Diphemanil Methylsulfate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.5673 mL | 12.8366 mL | 25.6733 mL | 51.3466 mL | 64.1832 mL |
| 5 mM | 0.5135 mL | 2.5673 mL | 5.1347 mL | 10.2693 mL | 12.8366 mL |
| 10 mM | 0.2567 mL | 1.2837 mL | 2.5673 mL | 5.1347 mL | 6.4183 mL |
| 50 mM | 0.0513 mL | 0.2567 mL | 0.5135 mL | 1.0269 mL | 1.2837 mL |
| 100 mM | 0.0257 mL | 0.1284 mL | 0.2567 mL | 0.5135 mL | 0.6418 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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Diphemanil Methylsulfate is a quaternary ammonium anticholinergic.
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[Electrophysiologic effects and arrhythmogenic potential of diphemanil methylsulfate on rabbit purkinje fibers. Correlations with clinical observations of QT prolongation in pediatrics].[Pubmed:9891832]
Arch Mal Coeur Vaiss. 1998 Dec;91(12):1487-94.
Serious undesirable cardiac side effects have been reported with treatment with Diphemanil Methylsulfate (Prantal) in premature babies or neonates. To understand the origin of this problem, the authors undertook an electrophysiological study of the effects of this product in vitro on rabbit Purkinje fibres. In three separate series (N = 5 to N = 8), the effects of increasing concentrations (0.1 microM-30 microM) of Diphemanil Methylsulfate, different frequencies of stimulation (0.2 Hz, 1 Hz, 2 Hz) and duration of exposition (60 min followed by 120 min washout) were observed on the properties of the action potential. The results show a clearcut antiarrhythmic Class III type action characterised by a concentration-dependent prolongation of the action potential duration with an inverse frequency dependency without significant changes of the other parameters. During stimulation at 0.2 Hz, early post-depolarizations and induced activity were observed in 3/8 of the fibres exposed to 10 microM and 8/8 fibres exposed to 30 microM. The effect did not attain a steady state after 60 min of exposition. It was not reversed by 120 min of washout of the preparation. These results were compatible with the reported cardiac arrhythmic effects of prolongation of the QT interval and torsades de pointe.
LC determination of diphemanil methylsulfate: application to stability study of stored pharmaceutical formulations.[Pubmed:12039622]
J Pharm Biomed Anal. 2002 Jun 1;28(5):811-8.
Diphemanil Methylsulfate (DMS) is a synthetic antimuscarinic agent classically used in infants for vagal hypertonia-related symptoms. A normal-phase, isocratic liquid chromatographic method was developed for the quantitative determination of DMS in bulk drugs and in pharmaceutical forms. The method has been completely validated and robustness of this method has been studied. The limit of detection (LOD) for DMS impurities namely, impurity 1 and 2 were found to be 11 and 46 ng/ml. The limit of quantitation (LOQ) was found to be 49 and 139 ng/ml for impurity 1 and 2, respectively. The stability studies have been performed for 2 and 10 mg DMS tablets subjected at various temperatures: 25 degrees C (long term storage condition) and 40 degrees C (accelerated storage condition) for 18 and 6 months, respectively. At 25 degrees C, the samples were found to be stable for the study period. At 40 degrees C, 2 and 10 mg DMS tablets showed degradation up to 5 and 10% over a 6-month period.
[Determinants of diphemanil methylsulfate (Prantal) utilization: a survey of practice in the French neonatal and intensive care units].[Pubmed:17175143]
Arch Pediatr. 2007 Mar;14(3):254-8.
UNLABELLED: Diphemanil Methylsulfate (Prantal) is a quaternary ammonium with parasympathicolytic properties. It is used in premature and term neonates with bradycardias related to vagal hyper reflectivity (HRV). OBJECTIVES: To assess the use of Prantal in the French neonatal and intensive care units: its indications, its modalities of use, its side effects and the number of patients treated during 1 year (2004) in France. METHODS: A questionnaire was electronically sent to all neonatology units and all neonatal intensive care units in France. RESULTS: Among 202 units, 121 (60%) answered the questionnaire. Prantal was reported to be used in 51 (42.1%) units. Among them, 38 (31.4%) actually treated 169 patients in 2004 with a mean number of patients treated by unit of 4. The diagnostic of HRV was supported by: a history of malaise (84.3%), bradycardia (94.1%), oculocardiac reflex (74.5%), cardiac Holter (76.4%), cardiorespirographic recording (19.6%), esophageal pHmetry (35.2%) and esophageal fibroscopy (21.5%). The mean starting dosing was 4.7 mg/kg/d, the mean maximal dosing was 9 mg/kg/d and the mean daily intakes were initially 2.3 and secondary 2.9. Prantal dosing was adjusted to weight in 54.9%, every month in 85.7%. Treatment was stopped at the mean post-natal age of 6 months, mostly in a progressive manner and without monitoring help. CONCLUSION: Prantal was seldom used in 2004 in France for different reasons: HRV is an uncertain entity, the efficacy of Prantal has not been validated and atropinic side effects can be encountered.
Cyclic guanosylmonophosphate urinary excretion in parasympathicomimetic or parasympatholytic syndromes induced by reserpine or diphemanil-methylsulfate.[Pubmed:10069489]
Life Sci. 1999;64(2):113-23.
Parasympathetic hyperactivity is found in some infants presenting faint episodes and could be responsible of certain Sudden Infant Death Syndrome cases. Therefore it was interesting to look for a noninvasive biochemical indicator of parasympathetic activity. A parasympaticomimetic syndrome associated with muscarinic receptor stimulation, which has been followed during 48 h, was obtained in the awake rat by reserpine injection (6.25 mg/kg at T0 and T24h), and a model of prolonged parasympatholytic syndrome, by administration of diphemanil-methylsulfate (DPMS), a muscarinic receptor inhibitor, in drinking water (mean daily dosis: 150 mg/kg). Significant bradycardia and tachycardia were respectively observed. In the reserpine-treated rats we found significantly increased cyclic guanosylmonophosphate (cGMP) urinary excretion between T24h and T48h, when compared with vehicle-treated controls (+87% in one experiment, +135% in the other, when expressed in pmol/microg creatinine); norepinephrine urinary excretion between T24h and T48h was decreased (-44%); the increase in cGMP urinary excretion was not significantly modified by the NO-synthase inhibitor, L-nitroarginine-methyl-ester. In the DPMS-treated rats, we observed a significantly decreased cGMP (-20%) and increased norepinephrine urinary excretion (+61%). Thus cGMP excretion varied in opposite directions in the reserpine- and DPMS-treated rats. The link between these modifications in cGMP excretion and muscarinic receptor stimulation or blockade has still to be fully demonstrated. Urinary cGMP excretion could be tested as screening parameter in infants at risk of faint episodes associated with bradycardia.
