Methscopolamine bromide
Basic information
- CAS
13265-10-6- Standard SMILES
C[N+]1(C)[C@@H]2CC(OC(=O)[C@H](CO)c3ccccc3)C[C@H]1[C@@H]1O[C@@H]12.[Br-]- InChIKey
CXYRUNPLKGGUJF-OZVSTBQFSA-M- Molecular formula
- C18H24BrNO4
- Average molar mass
- 398.3 g/mol
- Monoisotopic mass
- 397.08887
Overview
Scopolamine methobromide is a quaternary ammonium salt resulting from the reaction of the amino group of scopolamine with methyl bromide. It has a role as a muscarinic antagonist, a parasympatholytic, an antiemetic and an antispasmodic drug. It is a bromide salt and a quaternary ammonium salt. It is functionally related to a scopolamine.
Names & identifiers
- Preferred name
- Methscopolamine bromide
- IUPAC
- [(1R,2R,4S,5S)-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate bromide
- English name
- Methscopolamine bromide
- Molecular formula
- C18H24BrNO4
- Molecular weight
- 398.29
Names & synonyms
METHSCOPOLAMINE BROMIDE155-41-9scopolamine methyl bromideHoloponHyoscine Methobromidemethscopolamine(-)-scopolamine methobromide(-)-Scopolamine methyl bromideMethscopolamine (bromide)ProscomideHyoscine methyl bromideScopolamine methobromide
Show more names
blocandiopalnutroppamineampyroxholopan
N-Methylhyoscinium bromideMethylscopolamine bromideN-Methylscopolamine BromideMFCD00078560DTXSID2040608N-Methylhyoscine bromideRTN51LK7WLMLS000069754
Database identifiers
- CAS
13265-10-6、155-41-9- PubChem CID
- 5459110
- DTXSID
DTXSID2040608- ChEMBL
CHEMBL1354199、CHEMBL3091667- ChEBI
CHEBI:61276
Properties
Computed structural properties
- Topological polar surface area
- 59.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 454
Experimental & physicochemical properties
SolubilityFreely soluble
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section172.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 214 · 214-217 °C (decomp)
- refractive index
- -24 ° · -24 ° (C=1, H2O)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 2 O: · H2O: 50 mg/mL
- form
- powder
- color
- white
- optical activity
- 25 · [α]25/D 25°, c = 5 in H2O(lit.)
- Water Solubility
- 2 O: · H2O: 50mg/mL
- Merck
- 14 · 14,6003
- Stability
- Hygroscopic
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H312 (92.7%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P261, P271, P273, P280, P302+P352, P304+P340, P317, P321, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
REACH registered substance: N-methylhyoscinium bromide (EC: 205-844-5)
Methscopolamine bromide: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (92.7%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Methscopolamine bromide
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YM3675000
- ridadr
- UN 1544 6.1/PG 3
- hs_code
Chemistry & industry
Pharmacology
Pharmacodynamics
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.
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].
Mechanism of ActionMethscopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center). It does so by acting as a muscarinic antagonist.
Metabolism/MetabolitesLittle is known about the fate and excretion of methscopolamine.
FDA Pharmacological Classification
VDR09VTQ8U
METHSCOPOLAMINE
Established Pharmacologic Class [EPC] - Anticholinergic
Mechanisms of Action [MoA] - Cholinergic Antagonists
Methscopolamine is an Anticholinergic. The mechanism of action of methscopolamine is as a Cholinergic Antagonist.
METHSCOPOLAMINE BROMIDE
Absorption, Distribution and Excretion
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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