(-)-N-Methylscopolamine
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(-)-N-Methylscopolamine
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CAS No:
13265-10-6
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Formula:
C18H24NO4
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Chemical Name:
(-)-N-Methylscopolamine
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Synonyms:
3-Oxa-9-azoniatricyclo[3.3.1.02,4]nonane,7-[(2S)-3-hydroxy-1-oxo-2-phenylpropoxy]-9,9-dimethyl-,(1α,2β,4β,5α,7β)-;3-Oxa-9-azoniatricyclo[3.3.1.02,4]nonane,7-(3-hydroxy-1-oxo-2-phenylpropoxy)-9,9-dimethyl-,[7(S)-(1α,2β,4β,5α,7β)]-;1αH,5αH-Tropanium,6β,7β-epoxy-3α-hydroxy-8-methyl-,(-)-tropate (ester);3-Oxa-9-azatricyclo[3.3.1.02,4]nonane,3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane deriv.;(1α,2β,4β,5α,7β)-7-[(2S)-3-Hydroxy-1-oxo-2-phenylpropoxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane;Tropic acid,(-)-,ester with 6β,7β-epoxy-3α-hydroxy-8-methyl-1αH,5αH-tropanium;Methylscopolamine;N-Methylscopolamine;Methscopolamine;N-Methylhyoscine;(-)-N-Methylscopolamine;18905-44-7;52211-64-0;53832-46-5;56552-70-6
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CAS No:
Description
Methscopolamine is a 3-hydroxy carboxylic acid.|Methscopolamine is a quaternary ammonium derivative of scopolamine and antagonist at muscarininc (mACh) receptors. Methscopolamine bromide is the most common form of the active ingredient in oral pharmaceutical products. The oral tablets are used as an adjunct therapy for the treatment of peptic ulcer and is shown to be effective in decreasing the rate of recurrence of peptic ulcers as well as preventing complications.|Methscopolamine is an Anticholinergic. The mechanism of action of methscopolamine is as a Cholinergic Antagonist.|Scopolamine as a natural plant alkaloid that has potent anticholinergic effects and is used to treat mild to moderate nausea, motion sickness and allergic rhinitis. Scopolamine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.|A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.
(-)-N-Methylscopolamine Basic Attributes
318.4 g/mol
318.17053325 g/mol
VDR09VTQ8U
DTXSID0046931
WHITE CRYSTALS OR WHITE CRYSTALLINE POWDER
A - Alimentary tract and metabolism|S - Sensory organs
Characteristics
59.1 Ų
1.02150
In water, 1X10+6 mg/L at 25 °C (est)|INSOL IN ACETONE & IN CHLOROFORM
Methscopolamine bromide tablets should be stored in tight containers at 15 - 30 °C. /Methscopolamine bromide/
1.04X10-14 mm Hg at 25 °C (est)
ODORLESS
Henry's Law constant = 3.84X10-22 atm-cu m/mol at 25 °C (est)
Crystals from ethanol. MW: 398.29; decomposes at 214-217 °C. Freely soluble in water, in dilute ethanol; slightly soluble in absolute ethanol /Bromide/|MW: 380.39. Crystals. Freely soluble in water, dilute alcohol; slightly soluble in absolute alcohol. /Methylscopolamine nitrate/|Hydroxyl radical reaction rate constant = 5.5X10-12 cu cm/molec-sec at 25 °C (est)
Safety Information
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methscopolamine bromide, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Methscopolamine bromide/
Toxicity
Despite widespread use over many decades, neither scopolamine nor methscopolamine have been linked to episodes of liver enzyme elevations or clinically apparent liver injury. Scopolamine is metabolized by the liver, but is usually given in low doses (
IN ANESTHETIZED, SPONTANEOUSLY BREATHING DOGS, A 0.01% AEROSOL /OF METHSCOPOLAMINE BROMIDE/ INHIBITED ACETYLCHOLINE (IV OR AEROSOL)-INDUCED CHANGES IN PULMONARY MECHANICS. /METHSCOPOLAMINE BROMIDE/|Additive anticholinergic effects may result from concomitant use with antipsychotics, tricyclic antidepressants, and other drugs with anticholinergic effects. Concomitant administration with antacids may interfere with the absorption of methscopolamine bromide. /Methscopolamine bromide/
Drug Information
Scopolamine as a natural plant alkaloid that has potent anticholinergic effects and is used to treat mild to moderate nausea, motion sickness and allergic rhinitis. Scopolamine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.
Gastrointestinal Agents
Parasympatholytics|MEDICATION (VET): PRETREATMENT PROTECTED GUINEA PIGS AGAINST PHARMACOLOGICAL-INDUCED RESP COLLAPSE OR IMMUNOLOGICALLY-INDUCED ANAPHYLAXIS. IT IS LONG-LASTING BRONCHOSPASMOLYTIC WITH POTENTIAL FOR USE IN REVERSIBLE OBSTRUCTIVE LUNG DISORDERS.|Adjunctive therapy for the treatment of peptic ulcer.|Methscopolamine bromide is a quaternary ammonium derivative of scopolamine and therefore lacks the central actions of scopolamine. Its use has been limited chiefly to gastrointestinal diseases. It is less potent than atropine and is poorly absorbed; however, its action is more prolonged, ... . /Methscopolamine bromide/
Methscopolamine bromide is an anticholinergic agent which possesses most of the pharmacologic actions of that drug class. These may include reduction in volume and total acid content of gastric secretion, inhibition of gastrointestinal motility, inhibition of salivary excretion, dilation of the pupil and inhibition of accommodation with resulting blurring of vision. Large doses may result in tachycardia. /Methscopolamine bromide/|Use ... with caution in the elderly and in all patients with: autonomic neuropathy; hepatic or renal disease; or ulcerative colitis - large doses may suppress intestinal motility to the point of producing a paralytic ileus and for this reason precipitate or aggravate "toxic megacolon," a serious complication of the disease. The drug also should be used with caution in patients having hyperthyroidism, coronary heart disease, congestive heart failure, tachyrhythmia, tachycardia, hypertension, or prostatic hypertrophy. /Methscopolamine bromide/|Methscopolamine bromide may produce drowsiness or blurred vision. The patient should be cautioned regarding activities requiring mental alertness such as operating a motor vehicle or other machinery or performing hazardous work while taking this drug. /Methscopolamine bromide/|Diarrhea may be an early symptom of incomplete intestinal obstruction, especially in patients with ileostomy or colostomy. In this instance treatment with this drug would be inappropriate and possibly harmful. /Methscopolamine bromide/|For more Drug Warnings (Complete) data for METHYLSCOPOLAMINE (12 total), please visit the HSDB record page.
Methscopolamine bromide is an anticholinergic agent which possesses most of the pharmacologic actions of that drug class. These include reduction in volume and total acid content of gastric secretion, inhibition of gastrointestinal motility, inhibition of salivary excretion, dilation of the pupil and inhibition of accommodation with resulting blurring of vision. Large doses may result in tachycardia [Dailymed].
Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)
Methscopolamine bromide is a quaternary ammonium derivative of scopolamine. As a class, these agents are poorly and unreliably absorbed. Total absorption of quaternary ammonium derivatives of the alkaloids is 10-25%. Rate of absorption is not available. Quaternary ammonium salts have limited absorption from intact skin, and conjunctival penetration is poor. Little is known of the fate and excretion of most of these agents. Following oral administration, drug effects appear in about one hour and persist for 4 to 6 hours. Methscopolamine bromide has limited ability to cross the blood-brain barrier. The drug is excreted primarily in the urine and bile, or as unabsorbed drug in feces. There is no data on the presence of methscopolamine in breast milk; traces of atropine have been found after administration of atropine. /Methscopolamine bromide/|Methscopolamine bromide, like other quaternary ammonium drugs, is incompletely absorbed from the GI tract since it is completely ionized. Little information is available on the distribution or metabolic fate of methscopolamine bromide in the body. Quaternary ammonium antimuscarinics are completely ionized and possess poor lipid solubility. Accordingly, they do not readily penetrate the CNS or the eye. Methscopolamine bromide, like other quaternary ammonium compounds, is believed to be excreted principally in urine as unchanged drug and metabolites and in the feces as unabsorbed drug. Substantial amounts of orally administered drug are probably eliminated in feces as unabsorbed drug. /Methscopolamine bromide/
... Little information is available on the distribution or metabolic fate of methscopolamine bromide in the body. ... Methscopolamine bromide, like other quaternary ammonium compounds, is believed to be excreted principally in urine as unchanged drug and metabolites and in the feces as unabsorbed drug. ... /Methscopolamine bromide/
tropic acid; scopolamine hydrobromide; methylatropine bromide; apomethscopolamine bromide
Emergency and supportive measures: Maintain an open airway and assist ventilation if needed. Treat hyperthermia, coma, rhabdomyolysis, and seizures if they occur. /Anticholinergics/|Specific drugs and antidotes: A small dose of physostigmine .... can be given to patients with severe toxicity (e.g., hyperthermia, severe delirium, or tachycardia). Caution: Physostigmine can cause AV block, asystole, and seizures, especially in patients with tricyclic antidepressant overdose. Neostigmine, a peripherally acting cholinesterase inhibitor, may be useful in treating anticholinergic-induced ileus. /Anticholinergics/|Decontamination: Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. Because of slowed gastrointestinal motility, gut decontamination procedures may be helpful even in late-presenting patients. /Anticholinergics/|Enhanced elimination: Hemodialysis, hemoperfusion, peritoneal dialysis, and repeat-dose charcoal are not effective in removing anticholinergic agents. /Anticholinergics/|For more Antidote and Emergency Treatment (Complete) data for METHYLSCOPOLAMINE (7 total), please visit the HSDB record page.
/HUMAN EXPOSURE STUDIES/ TWELVE HEALTHY VOLUNTEERS WERE GIVEN IV INJECTIONS OF 100 UG EVERY 3 MIN FOR 5 DOSES ON SUCCESSIVE DAYS. MEAN HEART RATE FROM 2ND & 5TH INJECTIONS SIGNIFICANTLY GREATER THAN AFTER CORRESPONDING INJECTIONS OF 200 UG OF ATROPINE SULFATE.|/SIGNS AND SYMPTOMS/ The symptoms of overdosage ... progress from intensification of the usual side effects to CNS disturbances (from restlessness and excitement to psychotic behavior), circulatory changes (flushing, fall in blood pressure, circulatory failure), respiratory failure, paralysis, and coma.|/SIGNS AND SYMPTOMS/ With overdosage, a curare-like action may occur, i.e., neuromuscular blockade leading to muscular weakness and possible paralysis.
Bromide, N-Methylscopolamine
(-)-N-Methylscopolamine Use and Manufacturing
Prepared by action of methyl bromide on scopolamine base. /Methylscopolamine Bromide/|REACTION OF SCOPOLAMINE HYDROBROMIDE WITH METHYL BROMIDE IN BENZENE
(1979) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.|(1981) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.
ESSENTIALLY 100% AS AN ANTICHOLINERGIC FOR GASTROINTESTINAL DISEASES
Oral: Tablets: 2.5 mg Pamine (Bradley); 5 mg Pamine Forte (Bradley). /Methscopolamine bromide/
LIQUID CHROMATOGRAPHIC DETERMINATION OF METHSCOPOLAMINE BROMIDE IN VARIOUS VETERINARY FORMULATIONS.|Analyte: methscopolamine bromide; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards /methscopolamine bromide/|Analyte: methscopolamine bromide; matrix: chemical purity; procedure: liquid chromatography with ultraviolet detection at 210 nm with comparison to standards /methscopolamine bromide/|Analyte: methscopolamine bromide; matrix: pharmaceutical preparation (tablet); procedure: thin-layer chromatography with comparison to standards (chemical identification) /methscopolamine bromide/|Analyte: methscopolamine bromide; matrix: pharmaceutical preparation (tablet); procedure: liquid chromatography with ultraviolet detection at 254 nm with comparison to standards (chemical purity) /methscopolamine bromide/
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals
Computed Properties
Molecular Weight:318.4
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:318.17053325
Monoisotopic Mass:318.17053325
Topological Polar Surface Area:59.1
Heavy Atom Count:23
Formal Charge:1
Complexity:454
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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