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Diphemanil methylsulfate structure

Diphemanil methylsulfate

  • CAS:62-97-5
  • MW:389.51
  • MF:C20H24N.CH3O4S
 
1. Names and Identifiers
1.1 Name
Diphemanil methylsulfate
1.2 Synonyms
DIPHEMANIL METHYLSULFATE (500 MG) DISCON-TINUED; nivelona; p-(alpha-phenylbenzylidene)-1,1-dimethylpiperidiniummethylsulfate; prantal; prantalmethylsulfate; vagophemanil; vagophemanilmethylsulfate; variton;
1.3 CAS No.
62-97-5
1.5 EINECS
200-552-4
1.6 Molecular Formula
C20H24N.CH3O4S
1.7 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
1.8 InChkey
BREMLQBSKCSNNH-UHFFFAOYSA-M
1.9 Canonical Smiles
COS([O-])(=O)=O.C[N+]1(C)CCC(CC1)=C(C1=CC=CC=C1)C1=CC=CC=C1
1.10 Isomers Smiles
C[N+]1(CCC(=C(C2=CC=CC=C2)C3=CC=CC=C3)CC1)C.COS(=O)(=O)[O-]
2. Properties
2.1 StorageTemp
Inert atmosphere,Store in freezer, under -20°C
3. Use and Manufacturing
3.1 Description
Diphemanil methylsulfate (CAS 62-97-5) is a chemical compound that is commonly used in various applications. It appears as a white crystalline powder. The basic structure of diphemanil methylsulfate consists of a methylsulfate group attached to a diphemanil molecule. This compound is soluble in water and has physical properties such as a melting point of 190-195°C and a boiling point of 350-360°C. It also has a molecular weight of 428.56 g/mol.

Applicable Fields
Diphemanil methylsulfate has several applications in different fields:

Pharmaceutical Industry: In the pharmaceutical industry, diphemanil methylsulfate is used as an anticholinergic agent. It acts by blocking the effects of acetylcholine, a neurotransmitter, and helps in the treatment of various conditions such as peptic ulcers and gastrointestinal disorders.

Research and Laboratory: Diphemanil methylsulfate is also used in research and laboratory settings. It can be used as a reference standard or as a reagent in chemical reactions.

Storage Conditions
The storage conditions for diphemanil methylsulfate are to store it in a cool and dry place, away from direct sunlight.
4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Serious eye damage, Category 1

Acute toxicity - Inhalation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

H318 Causes serious eye damage

H330 Fatal if inhaled

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

P284 [In case of inadequate ventilation] wear respiratory protection.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P310 Immediately call a POISON CENTER/doctor/\u2026

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P320 Specific treatment is urgent (see ... on this label).

Storage

P405 Store locked up.

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

5.Other Information
Target
Value
Description
Diphemanil is a quaternary ammonium anticholinergic agent. It induces relaxation of isolated guinea pig trachea strips precontracted with methacholine (EC50 = 0.12 nM). Diphemanil reverses increases in lung resistance and decreases in dynamic lung compliance induced by the non-selective acetylcholine receptor agonist carbachol (carbamoylcholine; ) in vagotomized cats (ED50s = 17.5 and 19.3 μg/kg, respectively). It reduces salivation induced by the muscarinic acetylcholine receptor agonist pilocarpine in mice when administered subcutaneously at doses ranging from 1.25 to 10 mg/kg.
Originator
Pranta,Schering,US,1952
Uses
Diphemanil Methosulfate is an anticholinergic agent; a synthetic quaternary ammonium compound with anitmuscarinic properties used in the treatment of Frey''s syndrome and is used as a parasympatholytic bronchodilator agent.
Uses
Bronchodilatator;Anticholinergic
Definition
ChEBI: 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 stoma h acids, saliva and sweat, It is used topically in the treatment of hyperhidorsis (excessive sweating).
Manufacturing Process
(A) Preparation of diphenyl-(N-Methyl-4-Piperidyl)carbinol: to a Grignard solution prepared from 4.9 grams of magnesium, 100 cc of ether and 31.4 grams of dry
omobenzene is added 18.5 grams of 4-benzoyl-Nmethylpiperidine in 200 cc of dry ether. The reaction mixture is heated with stirring for 4 hours on the steam bath and then decomposed. The organic layer is separated and the aqueous layer extracted with benzene. The combined organic extracts are concentrated and the residue, diphenyl-(Nmethyl-4-piperidyl)carbinol, recrystallized from benzene-petroleum ether, MP 130-131°C. The Grignard complex may also be decomposed with ice and hydrochloric acid and the insoluble hydrochloride of the carbinol isolated directly.
(B) Preparation of diphenyl-(N-Methyl-4-Piperidylidene)methane: the carbinol can be dehydrated with 60% sulfuric acid. In general, to one part of the carbinol there is added 10 parts of 60% sulfuric acid. The mixture after heating for 6 hours is poured onto cracked ice, the solution made alkaline with dilute sodium hydroxide and the oily basic layer extracted with ether. The ether extracts after washing with water are dried over sodium sulfate, and after removing the ether, the residue is distilled in vacuo, MP 52°-53°C.
(C) Preparation of Final Product: The product from (B) is reacted with dimethyl sulfate in benzene to give the final product, MP 196°-197°C.
Brand name
Prantal (Schering).
Therapeutic Function
Spasmolytic
General Description
Diphemanil methylsulfate,4-(diphenylmethylene)-1,1-dimethylpiperidiniummethylsulfate (Prantal), or diphemanil methylsulfate is apotent cholinergic blocking agent. In the usual dosagerange, it acts as an effective parasympatholytic by blockingnerve impulses at the parasympathetic ganglia, but it doesnot invoke a sympathetic ganglionic blockade. It is claimedto be highly specific in its action on those innervations thatactivate gastric secretion and GI motility. Although thisdrug can produce atropine-like side effects, they rarelyoccur at recommended doses. The highly specific nature ofits action on gastric functions makes the drug useful inthe treatment of peptic ulcer, and its lack of atropine-likeeffects makes its use much less distressing than other antispasmodicdrugs. In addition to its action in decreasinggastric hypermotility, diphemanil methylsulfate is valuablein hyperhidrosis in low doses (50 mg twice daily) or topically.The drug is not well absorbed from the GI tract,particularly in the presence of food, and should be administeredbetween meals. The methylsulfate salt was chosen asthe best, because the chloride is hygroscopic and the bromideand iodide ions have exhibited toxic manifestations inclinical use.
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