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Homatropine Methylbromide
Also known as: Homatropine methylbromide, Homatropine methobromide, Omatropina metilbromuro, Methylhomatropine bromide, 80-49-9, 8-methylhomatropinium bromide
Molecular Formula
C17H24BrNO3
Molecular Weight
370.3  g/mol
InChI Key
FUFVKLQESJNNAN-UHFFFAOYSA-M

Homatropine Methylbromide is the methylbromide salt of homatropine, a synthetic tertiary amine alkaloid with antimuscarinic properties. Homatropine methylbromide, a competitive inhibitor of acetylcholine at the muscarinic receptor, blocks parasympathetic nerve stimulation, thereby inhibiting pepsin and gastrin secretion. When administered in high doses, this drug produces inhibitory effects on acetylcholine activity, specifically on smooth muscle located in the gastrointestinal, biliary, and genitourinary tracts, resulting in an anti-spasmodic effect.
1 2D Structure

Homatropine Methylbromide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl) 2-hydroxy-2-phenylacetate;bromide
2.1.2 InChI
InChI=1S/C17H24NO3.BrH/c1-18(2)13-8-9-14(18)11-15(10-13)21-17(20)16(19)12-6-4-3-5-7-12;/h3-7,13-16,19H,8-11H2,1-2H3;1H/q+1;/p-1
2.1.3 InChI Key
FUFVKLQESJNNAN-UHFFFAOYSA-M
2.1.4 Canonical SMILES
C[N+]1(C2CCC1CC(C2)OC(=O)C(C3=CC=CC=C3)O)C.[Br-]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Hmbromide

2. Homatropine Methylbromide

3. Homatropine Methylbromide Iodide, (3(r)-endo)-isomer

4. Homatropine Methylbromide Iodide, (3(s)-endo)-isomer

5. Homatropine Methylbromide, (3(r)-endo)-isomer

6. Homatropine Methylbromide, (3(s)-endo)-isomer

7. Homatropine Methylbromide, Endo-(+-)-isomer

2.2.2 Depositor-Supplied Synonyms

1. Homatropine Methylbromide

2. Homatropine Methobromide

3. Omatropina Metilbromuro

4. Methylhomatropine Bromide

5. 80-49-9

6. 8-methylhomatropinium Bromide

7. Tropinium Methobromide Mandelate

8. Homatropine Methyl Bromide

9. Methylhomatropinum Bromatum

10. Methylbromure D'homatropine

11. 3-alpha-hydroxy-8-methyl-1-alpha-h,5-alpha-h-tropanium Bromide Mandelate

12. Nsc34399

13. Schembl77827

14. Chebi:50373

15. Akos015896228

16. Db00725

17. 3-[2-hydroxy(phenyl)acetoxy]-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane Bromide

18. Ncgc00094694-01

19. Ncgc00094694-02

20. Db-056442

21. D90875

22. H-2560

2.3 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 370.3 g/mol
Molecular Formula C17H24BrNO3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass369.09396 g/mol
Monoisotopic Mass369.09396 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count22
Formal Charge0
Complexity374
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Indication

Used in conjunction with antacids or histamine H2-receptor antagonists in the treatment of peptic ulcers, gastric ulcers and duodenal ulcers, to reduce further gastric acid secretion and delay gastric emptying.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Homatropine methylbromide belongs to the group of medicines called anti-muscarinics. Homatropine is used to treat duodenal or stomach ulcers or intestine problems. It can be used together with antacids or other medicine in the treatment of peptic ulcer. It may also be used to prevent nausea, vomiting, and motion sickness.


5.2 ATC Code

A - Alimentary tract and metabolism

A03 - Drugs for functional gastrointestinal disorders

A03B - Belladonna and derivatives, plain

A03BB - Belladonna alkaloids, semisynthetic, quaternary ammonium compounds

A03BB06 - Homatropine methylbromide


5.3 Mechanism of Action

Homatropine is a quaternary ammonium muscarinic acetylcholine receptor antagonist. The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Homatropine methylbromide inhibits the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves as well as on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These postganglionic receptor sites are present in the autonomic effector cells of the smooth muscle, cardiac muscle, sinoatrial and atrioventricular nodes, and exocrine glands. Depending on the dose, anticholinergics may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder.


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