METHSCOPOLAMINE BROMIDE

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 Search

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

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 169 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2778	0.53 nM [Kd]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2778	0.55 nM [Kd]
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2778	1.38 nM [Kd]
Muscarinic acetylcholine receptor M4 86 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2778	0.44 nM [Kd]
Muscarinic acetylcholine receptor M5 62 Target ID: CHEMBL2035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616422	Antagonist 2778	0.59 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Peptic ulcer 72 Sources: https://www.drugs.com/pro/methscopolamine.html	Primary	Approved 8429	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 8429	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 8429	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
AK Scientific	8949AL
AbovChem LLC	HY-B0344
Alfa Chemistry	192392
Alfa Chemistry	ACM155419
Alfa Chemistry	ACM6106463
ApexBio Technology	B1611
AstaTech	C14926
AstaTech	T72700
BLD Pharm	BD137758
BOC Sciences	155-41-9
BioSynth	W-108020	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-108020.html
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
Frontier Scientific Services	500055859
Hairui	HR126304
Hairui	HR144027
KeyOrganics	DS-3286
Kingston Chemistry	KST-1A6213
Lab Network	LN00244382
Lab Network	LN01746362
MolPort	MolPort-016-633-266
MolPort	MolPort-035-395-028
MolPort	MolPort-039-337-899
Molnova	M12209
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
THE BioTek	bt-275692	https://www.thebiotek.com/product/inhibitors/bt-275692
THE BioTek	bt-367401	https://www.thebiotek.com/product/others/bt-367401
TargetMol	T0253
Tetrahedron	TS67187
Tetrahedron	TS80976
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
eMolecules	222575775
eMolecules	252380746
eMolecules	33497932
eMolecules	72976213
eMolecules	72980671
eNovation Chemicals	D674505	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674505
mcule	MCULE-2387598119
mcule	MCULE-4003028645
mcule	MCULE-7324716873
mcule	MCULE-9148232132

PubMed

Title	Date	PubMed
Effect of cholingeric drugs on methadone-induced catalepsy and stereotypies in rats treated chronically with methadone.	1976 Oct	987911
Central cholinergic mechanisms in L-DOPA induced hyperactive urinary bladder of the rat.	1982	7164219
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.	1997 Jul	9224827
Subtype-selective positive cooperative interactions between brucine analogues and acetylcholine at muscarinic receptors: radioligand binding studies.	1998 Mar	9495826
Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells.	1998 Nov	9846649
Allosteric effects of four stereoisomers of a fused indole ring system with 3H-N-methylscopolamine and acetylcholine at M1-M4 muscarinic receptors.	1999	10069518
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	10860942
A snake venom inhibitor to muscarinic acetylcholine receptor (mAChR): isolation and interaction with cloned human mAChR.	2000 May 15	10845706
Analogs of WIN 62,577 define a second allosteric site on muscarinic receptors.	2002 Dec	12435818
Zebrafish M2 muscarinic acetylcholine receptor: cloning, pharmacological characterization, expression patterns and roles in embryonic bradycardia.	2002 Nov	12411408
Bisquaternary dimers of strychnine and brucine. A new class of potent enhancers of antagonist binding to muscarinic M2 receptors.	2003 Jun 12	12757728
Pilocarpine-induced seizures in adult rats: monoamine content and muscarinic and dopaminergic receptor changes in the striatum.	2003 Oct	14559291
Modifications in muscarinic, dopaminergic and serotonergic receptors concentrations in the hippocampus and striatum of epileptic rats.	2005 Dec 5	16137708
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	15647330
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	15937215
Interaction studies of multiple binding sites on m4 muscarinic acetylcholine receptors.	2006 Aug	16709648
Allosteric site in M2 acetylcholine receptors: evidence for a major conformational change upon binding of an orthosteric agonist instead of an antagonist.	2006 Jan	16362429
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	16641315
Identification of various allosteric interaction sites on M1 muscarinic receptor using 125I-Met35-oxidized muscarinic toxin 7.	2006 May	16439611
Attenuation of cocaine's reinforcing and discriminative stimulus effects via muscarinic M1 acetylcholine receptor stimulation.	2010 Mar	19996296
Zinc oxide nanoparticle disruption of store-operated calcium entry in a muscarinic receptor signaling pathway.	2010 Oct	20708676

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.

Name

Type

Language

METHSCOPOLAMINE BROMIDE

Common Name

English

NSC-120606

Code

English

HYOSCINE METHOBROMIDE

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