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155-41-9 molecular structure
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(1S,5S,7R)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium bromide

ChemBase ID: 345
Molecular Formular: C18H24BrNO4
Molecular Mass: 398.29146
Monoisotopic Mass: 397.08887025
SMILES and InChIs

SMILES:
[Br-].C12C(O2)[C@H]2[N+]([C@H]1CC(C2)OC(=O)[C@@H](c1ccccc1)CO)(C)C
Canonical SMILES:
OC[C@H](c1ccccc1)C(=O)OC1C[C@H]2C3C([C@H](C1)[N+]2(C)C)O3.[Br-]
InChI:
InChI=1S/C18H24NO4.BrH/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11;/h3-7,12-17,20H,8-10H2,1-2H3;1H/q+1;/p-1/t12?,13-,14+,15+,16?,17?;/m1./s1
InChIKey:
CXYRUNPLKGGUJF-JIRGPDKYSA-M

Cite this record

CBID:345 http://www.chembase.cn/molecule-345.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,5S,7R)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium bromide
IUPAC Traditional name
(1S,5S,7R)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium bromide
Brand Name
Ampyrox
Blocan
Diopal
Holopon
Mescopil
Neo-Avagal
Nutrop
Pamine
Paraspan
Proscomide
Restropin
Transderm Scop
Daipin
Synonyms
Epoxymethamine Bromide
Epoxytropine Tropate Methylbromide
Hyoscine Methobromide
Hyoscine Methylbromide
Lescopine Bromide
N-Methylscopolammonium Bromide
N-Methylscopolamine Methylsulfate
N-Methylhyoscine Bromide
Methylscopolamine Hydrobromide
Methylscopolamine Bromide
Methscopolamine Methylbromide
Methscopolamine
Methoscopylamine Bromide
Scopolamine Methobromide
Scopolamine Methylbromide
Scopolamin Methylbromide
Methylscopolamine
CAS Number
155-41-9
PubChem SID
46506260
160963808
PubChem CID
23724781

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 15.14574  H Acceptors
H Donor LogD (pH = 5.5) -3.2673843 
LogD (pH = 7.4) -3.2673843  Log P -3.2673843 
Molar Refractivity 95.6349 cm3 Polarizability 33.79425 Å3
Polar Surface Area 55.76 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.96  LOG S -4.48 
Solubility (Water) 1.32e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Freely soluble expand Show data source
Hydrophobicity(logP)
-2.58 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00462 external link
Item Information
Drug Groups approved
Description A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors. [PubChem]
Indication Used as adjunctive therapy for the treatment of peptic ulcer. Also used to treat nausea and vomiting due to motion sickness.
Pharmacology Methscopolamine is a muscarinic antagonist structurally similar to the neurotransmitter acetylcholine and acts by blocking the muscarinic acetylcholine receptors and is thus classified as an anticholinergic. Methscopolamine has many uses including the prevention of motion sickness. It is not clear how Methscopolamine prevents nausea and vomiting due to motion sickness. The vestibular part of the ear is very important for balance. When a person becomes disoriented due to motion, the vestibule sends a signal through nerves to the vomiting center in the brain, and vomiting occurs. Acetylcholine is a chemical that nerves use to transmit messages to each other. It is believe that Methscopolamine prevents communication between the nerves of the vestibule and the vomiting center in the brain by blocking the action of acetylcholine. Methscopolamine also may work directly on the vomiting center. Methscopolamine must be taken before the onset of motion sickness to be effective.
Toxicity Symptoms of a methscopolamine overdose include headache, nausea, vomiting, dry mouth, difficulty swallowing, blurred vision, dilated pupils, hot, dry skin, dizziness; drowsiness, confusion, anxiety, seizures, weak pulse, and an irregular heartbeat. In addition, a curare-like action may occur, i.e., neuromuscular blockade leading to muscular weakness and possible paralysis.
Affected Organisms
Humans and other mammals
Biotransformation Little is known about the fate and excretion of methscopolamine.
Absorption Poorly and unreliably absorbed, total absorption is 10-25%.
External Links
Wikipedia

REFERENCES

REFERENCES

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