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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24NO4.Br
Molecular Weight 398.291
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHSCOPOLAMINE BROMIDE

SMILES

[Br-].[H][C@@]12O[C@]1([H])[C@H]3C[C@H](C[C@@H]2[N+]3(C)C)OC(=O)[C@H](CO)C4=CC=CC=C4

InChI

InChIKey=CXYRUNPLKGGUJF-RAFJPFSSSA-M
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

HIDE SMILES / InChI
Methscopolamine bromide is an anticholinergic agent used along with other medications to treat peptic ulcers by reducing stomach acid secretion. Methscopolamine is also commonly used as a drying agent, to dry up post-nasal drip, in cold, irritable bowel syndrome and allergy medications. Methscopolamine binds to M1-M5 isoforms of muscarinic receptors.

CNS Activity

Curator's Comment: Methscopolamine bromide has limited ability to cross the blood-brain-barrier

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PAMINE

Approved Use

Methscopolamine bromide is an anticholinergic agent which possesses most of the pharmacological 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.

Launch Date

1953
Palliative
DALLERGY

Approved Use

This product provides relief of the symptoms resulting from irritation of sinus, nasal, and upper respiratory tract tissue. Phenylephrine exerts a vasoconstrictive and decongestive action while chlorpheniramine maleate decreases the symptoms of watering eyes, post nasal drip, and sneezing. Methscopolamine nitrate further augments the antisecretory activity of this product.
Palliative
DALLERGY

Approved Use

This product provides relief of the symptoms resulting from irritation of sinus, nasal, and upper respiratory tract tissue. Phenylephrine exerts a vasoconstrictive and decongestive action while chlorpheniramine maleate decreases the symptoms of watering eyes, post nasal drip, and sneezing. Methscopolamine nitrate further augments the antisecretory activity of this product.
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Effect of cholingeric drugs on methadone-induced catalepsy and stereotypies in rats treated chronically with methadone.
1976 Oct
Central cholinergic mechanisms in L-DOPA induced hyperactive urinary bladder of the rat.
1982
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
1997 Jul
Subtype-selective positive cooperative interactions between brucine analogues and acetylcholine at muscarinic receptors: radioligand binding studies.
1998 Mar
Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells.
1998 Nov
Allosteric effects of four stereoisomers of a fused indole ring system with 3H-N-methylscopolamine and acetylcholine at M1-M4 muscarinic receptors.
1999
Allosteric interactions of staurosporine and other indolocarbazoles with N-[methyl-(3)H]scopolamine and acetylcholine at muscarinic receptor subtypes: identification of a second allosteric site.
2000 Jul
A snake venom inhibitor to muscarinic acetylcholine receptor (mAChR): isolation and interaction with cloned human mAChR.
2000 May 15
Analogs of WIN 62,577 define a second allosteric site on muscarinic receptors.
2002 Dec
Zebrafish M2 muscarinic acetylcholine receptor: cloning, pharmacological characterization, expression patterns and roles in embryonic bradycardia.
2002 Nov
Bisquaternary dimers of strychnine and brucine. A new class of potent enhancers of antagonist binding to muscarinic M2 receptors.
2003 Jun 12
Pilocarpine-induced seizures in adult rats: monoamine content and muscarinic and dopaminergic receptor changes in the striatum.
2003 Oct
Modifications in muscarinic, dopaminergic and serotonergic receptors concentrations in the hippocampus and striatum of epileptic rats.
2005 Dec 5
Asparagine, valine, and threonine in the third extracellular loop of muscarinic receptor have essential roles in the positive cooperativity of strychnine-like allosteric modulators.
2005 May
Critical amino acid residues of the common allosteric site on the M2 muscarinic acetylcholine receptor: more similarities than differences between the structurally divergent agents gallamine and bis(ammonio)alkane-type hexamethylene-bis-[dimethyl-(3-phthalimidopropyl)ammonium]dibromide.
2005 Sep
Interaction studies of multiple binding sites on m4 muscarinic acetylcholine receptors.
2006 Aug
Allosteric site in M2 acetylcholine receptors: evidence for a major conformational change upon binding of an orthosteric agonist instead of an antagonist.
2006 Jan
Allosteric interactions with muscarinic acetylcholine receptors: complex role of the conserved tryptophan M2422Trp in a critical cluster of amino acids for baseline affinity, subtype selectivity, and cooperativity.
2006 Jul
Identification of various allosteric interaction sites on M1 muscarinic receptor using 125I-Met35-oxidized muscarinic toxin 7.
2006 May
Attenuation of cocaine's reinforcing and discriminative stimulus effects via muscarinic M1 acetylcholine receptor stimulation.
2010 Mar
Zinc oxide nanoparticle disruption of store-operated calcium entry in a muscarinic receptor signaling pathway.
2010 Oct
Patents

Patents

Sample Use Guides

The average dosage of Methscopolamine Bromide Tablets USP is 2.5 mg one-half hour before meals and 2.5 to 5 mg at bedtime. A starting dose of 12.5 mg daily will be clinically effective in most patients without the production of appreciable side effects.
Route of Administration: Oral
In Vitro Use Guide
In the standard assay, mAChR subtypes (20-30 fmol/tube) in particulate fractions of Sf9 cells were incubated with 4 to 4.2 nM [3H]NMS (methscopolamine) and different concentrations of muscarinic ligands in 20 mM K-phosphate buffer (pH 7). Bound [3H]NMS trapped on the filter was counted with a liquid scintillation counter.
Name Type Language
METHSCOPOLAMINE BROMIDE
MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
NSC-120606
Code English
HYOSCINE METHOBROMIDE
MART.   WHO-DD  
Common Name English
3-OXA-9-AZONIATRICYCLO(3.3.1.0(SUP 2,4))NONANE, 7-(3-HYDROXY-1-OXO-2-PHENYLPROPOXY)-9,9-DIMETHYL-, BROMIDE, (7(S)-(1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.))-
Common Name English
METHSCOPOLAMINE BROMIDE [ORANGE BOOK]
Common Name English
PAMINE
Brand Name English
METHSCOPOLAMINE BROMIDE [USP-RS]
Common Name English
Hyoscine methobromide [WHO-DD]
Common Name English
HOLOPON
Brand Name English
6.BETA.,7.BETA.-EPOXY-3.ALPHA.-HYDROXY-8-METHYL-1.ALPHA.H,5.ALPHA.H-TROPANIUM BROMIDE (-)-TROPATE
Common Name English
HYOSCINE METHOBROMIDE [MART.]
Common Name English
METHSCOPOLAMINE BROMIDE [USP MONOGRAPH]
Common Name English
METHSCOPOLAMINE BROMIDE [VANDF]
Common Name English
SCOPOLAMINE METHYL BROMIDE [MI]
Common Name English
N-METHYLSCOPOLAMINE BROMIDE
Common Name English
METHSCOPOLAMINE BROMIDE [MI]
Common Name English
(1R,2R,4S,5S,7s)-7-[[(2S)-3-hydroxy-2-phenylpropanoyl]oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide
Common Name English
BROMIDE SALT OF OXITROPIUM BROMIDE IMPURITY B [EP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:02:18 GMT 2023 , Edited by admin on Fri Dec 15 15:02:18 GMT 2023
Code System Code Type Description
EVMPD
SUB14157MIG
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WIKIPEDIA
Methylscopolamine bromide
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RS_ITEM_NUM
1421009
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FDA UNII
RTN51LK7WL
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SMS_ID
100000077627
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CAS
155-41-9
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RXCUI
56092
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PRIMARY RxNorm
NCI_THESAURUS
C47612
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IUPHAR
316
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ECHA (EC/EINECS)
205-844-5
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DRUG BANK
DB00462
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MERCK INDEX
m7347
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PRIMARY Merck Index
DAILYMED
RTN51LK7WL
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NSC
120606
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CHEBI
61276
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MERCK INDEX
m9813
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ChEMBL
CHEMBL1201268
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EPA CompTox
DTXSID2040608
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LACTMED
Methscopolamine Bromide
Created by admin on Fri Dec 15 15:02:18 GMT 2023 , Edited by admin on Fri Dec 15 15:02:18 GMT 2023
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