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Diphenmanil (methylsulfate)

CAT: 0804-HY-16171-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-16171-01Size:5 mg
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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.
CAS Number
62-97-5
Product Name Alternative
Diphemanil mesylate
UNSPSC
12352005
Hazard Statement
H301, H318, H334
Target
MAChR
Type
Reference compound
Related Pathways
GPCR/G Protein; Neuronal Signaling
Field of Research
Endocrinology
Assay Protocol
https://www.medchemexpress.com/diphenmanil-methylsulfate.html
Purity
99.74
Solubility
H2O : 16.67 mg/mL (ultrasonic)
Smiles
[O-]S(=O)(OC)=O.C[N+]1(C)CC/C(CC1)=C(C2=CC=CC=C2)\C3=CC=CC=C3
Molecular Formula
C21H27NO4S
Molecular Weight
389.51
Precautions
H301, H318, H334
References & Citations
[1]Küng M, Diamond L. Effect of inhaled diphemanil methylsulfate, a parasympatholytic agent, on histamine induced bronchoconstriction in asymptomatic asthmatics. Ann Allergy. 1984 Jan;52 (1) :22-5.|[2]Vidal AM, Rey E, Pons G et al. Pharmacokinetics of diphemanil methylsulphate in healthy subjects. Eur J Clin Pharmacol. 1992;42 (6) :689-91.|[3]Vidal AM, Chéron G, Rey E et al. Pharmacokinetics of diphemanil methylsulphate in infants. Eur J Clin Pharmacol. 1993;45 (1) :89-91.|[4]Chéron G, Vidal AM, Rey E et al. [Pharmacokinetics of diphemanil methylsulfate in infants]. Arch Pediatr. 1994 Jan;1 (1) :33-7.|[5]Adamantidis M, Dumotier B, Caron J, Dupuis B. [Electrophysiologic effects and arrhythmogenic potential of diphemanil methylsulfate on rabbit purkinje fibers. Correlations with clinical observations of QT prolongation in pediatrics]. Arch Mal Coeur Vaiss. 1998 Dec;91 (12) :1487-94.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Diphemanil methyl sulfate

Diphemanil methylsulfate is the alkene resulting from the formal Wittig olefination of benzophenone and 1,1-dimethyl-4-bromopiperidinium methylsulfate. A quaternary ammonium anticholinergic, it binds muscarinic acetycholine receptors and thereby decreases secretory excretion of stomach acids, saliva and sweat, It is used topically in the treatment of hyperhidorsis (excessive sweating). It has a role as a bronchodilator agent, a muscarinic antagonist and a parasympatholytic. It is a member of piperidines and a quaternary ammonium salt.

CAS Number62-97-5
PubChem CID6126
IUPAC Name4-benzhydrylidene-1,1-dimethylpiperidin-1-ium;methyl sulfate
Molecular FormulaC21H27NO4S
Molecular Weight389.5
Topological Polar Surface Area74.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Heavy Atom Count27
Formal Charge0
Complexity426
SMILES
C[N+]1(CCC(=C(C2=CC=CC=C2)C3=CC=CC=C3)CC1)C.COS(=O)(=O)[O-]
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
InChIKey
BREMLQBSKCSNNH-UHFFFAOYSA-M
Chemical Structure
2D Structure
2D structure of Diphemanil methyl sulfate
CAS: 62-97-5
CID: 6126
Formula: C21H27NO4S
MW: 389.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight389.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass389.16607952
Monoisotopic Mass389.16607952
Topological Polar Surface Area74.8 Ų
Heavy Atom Count27
Formal Charge0
Complexity426
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
T0594-01Diphenmanil methylsulfate
A16513-50Diphenmanil methylsulfate 50mg
A16513-5Diphenmanil methylsulfate 5mg
A16513-500Diphenmanil methylsulfate 500mg
A16513-100Diphenmanil methylsulfate 100mg
A16513-200Diphenmanil methylsulfate 200mg
A16513-25Diphenmanil methylsulfate 25mg
A16513-10Diphenmanil methylsulfate 10mg
A16513-10mM-DDiphenmanil methylsulfate 10mM * 1mL in DMSO
T5327-01Amezinium methylsulfate

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