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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

Molecular Formula C18H23NO4
Molecular Weight 317.3795
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

-5.27990391E11
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
Subtype-selective positive cooperative interactions between brucine analogues and acetylcholine at muscarinic receptors: radioligand binding studies.
1998 Mar
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
Analogs of WIN 62,577 define a second allosteric site on muscarinic receptors.
2002 Dec
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
Interaction studies of multiple binding sites on m4 muscarinic acetylcholine receptors.
2006 Aug
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:18 UTC 2023
Edited
by admin
on Fri Dec 15 15:02:18 UTC 2023
Record UNII
RTN51LK7WL
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
Code System Code Type Description
EVMPD
SUB14157MIG
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
WIKIPEDIA
Methylscopolamine bromide
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
RS_ITEM_NUM
1421009
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
FDA UNII
RTN51LK7WL
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
SMS_ID
100000077627
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
CAS
155-41-9
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
RXCUI
56092
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C47612
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
IUPHAR
316
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-844-5
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
DRUG BANK
DB00462
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
MERCK INDEX
m7347
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY Merck Index
DAILYMED
RTN51LK7WL
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
NSC
120606
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
CHEBI
61276
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
MERCK INDEX
m9813
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201268
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
EPA CompTox
DTXSID2040608
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
LACTMED
Methscopolamine Bromide
Created by admin on Fri Dec 15 15:02:18 UTC 2023 , Edited by admin on Fri Dec 15 15:02:18 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY