Basic information
- CAS
80-49-9- Standard SMILES
C[N+]1(C)C2CCC1CC(OC(=O)C(O)c1ccccc1)C2.[Br-]- InChIKey
FUFVKLQESJNNAN-UHFFFAOYSA-M- Molecular formula
- C17H24BrNO3
- Average molar mass
- 370.3 g/mol
- Monoisotopic mass
- 369.09396
Overview
Homatropine methylbromide is an azabicycloalkane and an organic bromide salt. It has a role as a muscarinic antagonist, an anti-ulcer drug and an antispasmodic drug.
Names & identifiers
- Preferred name
- Homatropine Methylbromide
- IUPAC
- (8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl) 2-hydroxy-2-phenylacetate bromide
- English name
- Homatropine methyl bromide
- Molecular formula
- C17H24NO3.Br
- Molecular weight
- 370.28
Names & synonyms
homatropine methylbromide80-49-9Methylhomatropine bromideOmatropina metilbromuro8-Methylhomatropinium bromideEquipinTropinium methobromide mandelateMethylhomatropinum bromatumHomapin-5Homatropini methylbromidumMethylbromure d'homatropineMetilbromuro de homatropina
Show more names
ESOPINsethylD02070homapinmesopinHOMOLONEnovatrinsed-temsendo-mid
Homapin-103-alpha-Hydroxy-8-methyl-1-alpha-H,5-alpha-H-tropanium bromide mandelateCHEBI:503733-[(2-hydroxy-2-phenylacetyl)oxy]-8,8-dimethyl-8-azabicyclo[3.2.1]octan-8-ium bromideDTXSID4023127HMBromideNSC-34399NSC-757048
Database identifiers
- CAS
80-49-9- PubChem CID
- 6646
- ChEMBL
CHEMBL1200851
Properties
Computed structural properties
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 373
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point191-192 °C
Physicochemical properties
- Melting point
- 192 °C · 192°C
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- 96 per · Freely soluble in water, soluble in ethanol 96 per cent
- form
- Solid
- color
- White to Off-White
- Merck
- 14 · 14,4730
- CAS DataBase Reference
- 80 · 80-49-9(CAS DataBase Reference)
- FDA 21 CFR
- 310.545 · 310.545
- FDA UNII
- 68 JRS2HC1C · 68JRS2HC1C
- ATC code
- 3 BB06 · A03BB06
- EPA Substance Registry System
- Homatropine methylbromide (80-49-9)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.5% (1 of 66) of reports.
Warning
H302 (98.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 66 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Other Safety InformationIMAP assessments - 8-Azoniabicyclo[3.2.1]octane, 3-[(hydroxyphenylacetyl)oxy]-8,8-dimethyl-, bromide, endo-(.+-.)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (98.5%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- MS9000000
- ridadr
- 1544
- hs_code
- 29399990
- Toxicity
- LD50 in mice (mg/kg): 1400 orally, 60 i.p. (Cahen, Tvede)
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-26-36
- hazard_class
- 6.1
- packing_group
- III
- Hazard statements
- H302
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Pharmacodynamics
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.
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.
Uses & manufacturing
General Manufacturing Information8-Azoniabicyclo[3.2.1]octane, 3-[(2-hydroxy-2-phenylacetyl)oxy]-8,8-dimethyl-, bromide (1:1), (3-endo)-: INACTIVE
Applications
UsesHomatropine methylbromide or Methylhomatropine bromide is a quaternary ammonium salt of methylhomatropine. Methylhomatropine is a peripherally acting anticholinergic medication that inhibits muscarinic acetylcholine receptors and thus the parasympathetic nervous system. Methylhomatropine does not cross the blood–brain barrier. Methylhomatropine is used, in addition to papaverine, as component of mild drugs that help "flush" the bile.
Related reactions
0 records
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Compound notes
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