| Identification | Back Directory | [Name]
Diphemanil Methylsulfate | [CAS]
62-97-5 | [Synonyms]
prantal
variton
Talpran
demotil
nivelona
diphemanil
diphenatil
vagophemanil
diphenmethanil
Diphemanil mesylate
prantalmethylsulfate
diphemanil metilsulfate
diphemanilmethylsulfate
DIPHEMANIL METHYLSULFAT
diphenmanilmethylsulfate
Diphenmanil methosulfate
vagophemanilmethylsulfate
diphenmethanilmethylsulfate
Diphemanil Methylsulfate USP/EP/BP
4-benzhydrylidene-1,1-dimethylpiperidin-1-ium
4-benzhydrylidene-1,1-dimethyl-piperidin-1-ium
DIPHEMANIL METHYLSULFATE (500 MG) DISCON-TINUED
4-(diphenylmethylene)-1,1-dimethyl-piperidiniumethylsulfate
4-(diphenylmethylene)-1,1-dimethylpiperidiniummethylsulfate
n,n-dimethyl-4-piperidylidene-1,1-diphenylmethanemethylsulfate
4-(Diphenylmethylene)-1,1-dimethylpiperidin-1-ium Methyl Sulfate
p-(alpha-phenylbenzylidene)-1,1-dimethylpiperidiniummethylsulfate
Piperidinium, 4-(diphenylmethylene)-1,1-dimethyl-, methyl sulfate
Piperidinium, 4-(diphenylmethylene)-1,1-dimethyl-, methyl sulfate (1:1) | [EINECS(EC#)]
200-552-4 | [Molecular Formula]
C20H24N.CH3O4S | [MDL Number]
MFCD00865157 | [MOL File]
62-97-5.mol | [Molecular Weight]
389.51 |
| Chemical Properties | Back Directory | [Melting point ]
194-195℃ | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [solubility ]
: 16.67 mg/mL (42.80 mM; Need ultrasonic) | [Water Solubility ]
Soluble in water | [form ]
powder to crystal | [color ]
White to Almost white | [Stability:]
Hygroscopic |
| Safety Data | Back Directory | [HS Code ]
2933.39.4100 | [Toxicity]
LD50 in rats, mice, guinea pigs (mg/kg): 1107, 64, 404 orally (Margolin) |
| Hazard Information | Back Directory | [Description]
Diphemanil is a quaternary ammonium anticholinergic agent.1 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; Item No. 14486) 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.2 | [Originator]
Pranta,Schering,US,1952 | [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. | [References]
[1] L DIAMOND M O. A comparative study of two parasympatholytic bronchodilator agents: ipratropium bromide and diphemanil methylsulfate.[J]. Journal of Pharmacology and Experimental Therapeutics, 1981, 216 1: 1-5.
[2] RICHTER W. Estimation of Anticholinergic Drug Effects in Mice by Antagonism against Pilocarpine-Induced Salivation1[J]. Basic & Clinical Pharmacology & Toxicology, 1966, 24 2-3: 243-254. DOI: 10.1111/j.1600-0773.1966.tb00387.x |
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