METHSCOPOLAMINE BROMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H24NO4.Br
Molecular Weight	398.291
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].C[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]3O[C@@H]23)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	BrH
Molecular Weight	80.912
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H23NO4
Molecular Weight	317.3795
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	6 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/pro/methscopolamine.html

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M1 168 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2849	0.53 nM [Kd]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2849	0.55 nM [Kd]
Muscarinic acetylcholine receptor M3 160 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2849	1.38 nM [Kd]
Muscarinic acetylcholine receptor M4 87 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2849	0.44 nM [Kd]
Muscarinic acetylcholine receptor M5 63 Target ID: CHEMBL2035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2849	0.59 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Peptic ulcer 72 Sources: https://www.drugs.com/pro/methscopolamine.html	Primary	Approved 8583	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
Allergy 44 Sources: https://www.drugs.com/pro/dallergy-chewable-tablets.html	Palliative	Approved 8583	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.
Common cold 58 Sources: https://www.drugs.com/pro/dallergy-chewable-tablets.html	Palliative	Approved 8583	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

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003RYY
AAA Chemistry	AR-1A1120
ABI Chem	AC1Q60OB
AbovChem LLC	HY-B0344
AK Scientific	8949AL
Alfa Chemistry	192392
Alfa Chemistry	ACM155419
Alfa Chemistry	ACM6106463
ApexBio Technology	B1611
AstaTech	C14926
AstaTech	T72700
BioSynth	W-108020	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-108020.html
BLD Pharm	BD137758
BOC Sciences	155-41-9
Chem-Impex International	32523
Chem-Impex International	32524
ChemShuttle	151550
ChemTik	CTK5A5327
Combi-Blocks	QH-1625
Compound Cloud	23724781
Compound Cloud	23724782
Compound Cloud	23724825
eMolecules	222575775
eMolecules	252380746
eMolecules	33497932
eMolecules	72976213
eMolecules	72980671
eNovation Chemicals	D674505	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674505
Frontier Scientific Services	500055859
Hairui	HR126304
Hairui	HR144027
KeyOrganics	DS-3286
Kingston Chemistry	KST-1A6213
Lab Network	LN00244382
Lab Network	LN01746362
mcule	MCULE-2387598119
mcule	MCULE-4003028645
mcule	MCULE-7324716873
mcule	MCULE-9148232132
Molnova	M12209
MolPort	MolPort-016-633-266
MolPort	MolPort-035-395-028
MolPort	MolPort-039-337-899
MuseChem	A000818
MuseChem	M066232
NCI Plated 2007	120606
NCI Plated 2007	61809
NovoSeek	71183
Ryan Scientific	Nisoldipine
Selleck Chemicals	S1978
Sigma Aldrich	1421009\|USP
Sigma Aldrich	S2250
Sigma Aldrich	S2250\|SIGMA
Sigma Aldrich	S8502\|SIGMA
Sigma Aldrich	Y0000715
Smolecule	S535235	http://www.smolecule.com/products/s535235
Smolecule	S571141	https://www.smolecule.com/products/s571141
StruChem	SC-20636
TargetMol	T0253
Tetrahedron	TS67187
Tetrahedron	TS80976
THE BioTek	bt-275692	https://www.thebiotek.com/product/inhibitors/bt-275692
THE BioTek	bt-367401	https://www.thebiotek.com/product/others/bt-367401
TimTec	ST102880
Toronto Research Chemicals	C255030
Toronto Research Chemicals	S200050
Toronto Research Chemicals	S200068
Wonderchem	WD06FT9
ZINC	ZINC000100027531	http://zinc15.docking.org/substances/ZINC000100027531
ZINC	ZINC000100036751	http://zinc15.docking.org/substances/ZINC000100036751
ZINC	ZINC000100036760	http://zinc15.docking.org/substances/ZINC000100036760
ZINC	ZINC000100069023	http://zinc15.docking.org/substances/ZINC000100069023
ZINC	ZINC000100743529	http://zinc15.docking.org/substances/ZINC000100743529

PubMed

Title	Date	PubMed
Zinc oxide nanoparticle disruption of store-operated calcium entry in a muscarinic receptor signaling pathway.	2010-10	20708676
Attenuation of cocaine's reinforcing and discriminative stimulus effects via muscarinic M1 acetylcholine receptor stimulation.	2010-03	19996296
Interaction studies of multiple binding sites on m4 muscarinic acetylcholine receptors.	2006-08	16709648
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.	2006-07	16641315
Identification of various allosteric interaction sites on M1 muscarinic receptor using 125I-Met35-oxidized muscarinic toxin 7.	2006-05	16439611
Allosteric site in M2 acetylcholine receptors: evidence for a major conformational change upon binding of an orthosteric agonist instead of an antagonist.	2006-01	16362429
Modifications in muscarinic, dopaminergic and serotonergic receptors concentrations in the hippocampus and striatum of epileptic rats.	2005-12-05	16137708
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.	2005-09	15937215
Asparagine, valine, and threonine in the third extracellular loop of muscarinic receptor have essential roles in the positive cooperativity of strychnine-like allosteric modulators.	2005-05	15647330
Pilocarpine-induced seizures in adult rats: monoamine content and muscarinic and dopaminergic receptor changes in the striatum.	2003-10	14559291
Bisquaternary dimers of strychnine and brucine. A new class of potent enhancers of antagonist binding to muscarinic M2 receptors.	2003-06-12	12757728
Analogs of WIN 62,577 define a second allosteric site on muscarinic receptors.	2002-12	12435818
Zebrafish M2 muscarinic acetylcholine receptor: cloning, pharmacological characterization, expression patterns and roles in embryonic bradycardia.	2002-11	12411408
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.	2000-07	10860942
A snake venom inhibitor to muscarinic acetylcholine receptor (mAChR): isolation and interaction with cloned human mAChR.	2000-05-15	10845706
Allosteric effects of four stereoisomers of a fused indole ring system with 3H-N-methylscopolamine and acetylcholine at M1-M4 muscarinic receptors.	1999	10069518
Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells.	1998-11	9846649
Subtype-selective positive cooperative interactions between brucine analogues and acetylcholine at muscarinic receptors: radioligand binding studies.	1998-03	9495826
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.	1997-07	9224827
Central cholinergic mechanisms in L-DOPA induced hyperactive urinary bladder of the rat.	1982	7164219
Effect of cholingeric drugs on methadone-induced catalepsy and stereotypies in rats treated chronically with methadone.	1976-10	987911

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 17:36:14 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:14 GMT 2025`
Record UNII	RTN51LK7WL
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

HYOSCINE METHOBROMIDE

Preferred Name

English

METHSCOPOLAMINE BROMIDE

Common Name

English

NSC-120606

Code

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

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