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ANISOTROPINE METHYLBROMIDE

CAS：80-50-2
MW:362.35
MF：C17H32BrNO2

Anisotropine Methylbromide is a antichloindergic agent and has been used for relief of gastrointestinal spasm and for the suppression of gastric acid secretion. Anisotropine Methylbromide was found to be potentially useful in the treatment of duodenal ulcer disease. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: ANISOTROPINE METHYLBROMIDE

1.2 Synonyms: 1,3,5-trideuterio-2-methoxy-benzene; 1-alpha-h,5-alpha-h-tropanium,3-alpha-hydroxy-8-methyl-,bromide,2-propylvale; 1alphah,5alphah-tropanium,3alpha-hydroxy-8-methyl-,bromide,2-propylvalerate; 2,4,6-Trideuterio-anisol; 2,4,6-trideuterioanisole; 2,4,6-Trideutero-anisol; 2-propylpentanoyltropiniummethylbromide; 3-alpha-hydroxy-8-methyl-1-alpha-h,5-alpha-h-tropaniumbromide2-propylvalera; 3alpha-hydroxy-8-methyl-1alphah,5alphah-tropaniumbromide2-propylvalerate; 8-METHYL-3-[2-PROPYLPENTANOYLOXY]TROPINIUM BROMIDE; Anisole-2,4,6-d3; anisotropine methobromide; anisotropine methyl bromide; CHOLINE IODIDE 1-HYDROXY-α-PHENYLCYCLOPENTANEACETATE; Methoxy(benzene-2,4,6-d3); OCTATROPINE METHYLBROMIDE;

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1.3 CAS No.: 80-50-2

1.4 CID: 657201

1.5 EINECS: 201-285-6

1.6 Molecular Formula: C17H32BrNO2

1.7 Inchi: InChI=1/C17H32NO2.BrH/c1-5-7-13(8-6-2)17(19)20-16-11-14-9-10-15(12-16)18(14,3)4;/h13-16H,5-12H2,1-4H3;1H/q+1;/p-1

1.8 InChkey: QSFKGMJOKUZAJM-UHFFFAOYNA-M

1.9 Canonical Smiles: [Br-].CCCC(CCC)C(=O)OC1CC2CCC(C1)[N+]2(C)C

1.10 Isomers Smiles: CCCC(CCC)C(=O)OC1C[C@H]2CC[C@@H](C1)[N+]2(C)C.[Br-]

2. Properties

2.1 Storage: 2-8°C

2.2 Color/Form: CRYSTALS FROM ACETONE
WHITE, GLISTENING POWDER OR PLATES

2.3 Odor: PROBABLY ODORLESS

2.4 Water Solubility: SOL IN WATER, CHLOROFORM; SPARINGLY SOL IN ALCOHOL; SLIGHTLY SOL IN ACETONE; INSOL IN ETHER
SOL IN ETHANOL; INSOL IN DIETHYL ETHER

2.5 Stability: STABLE IN LIGHT, HEAT, & AIR.

2.6 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A quaternary ammonium salt resulting from the reaction of the amino group of anisotropine with methyl bromide.

3.2 Description: ChEBI: A quaternary ammonium salt resulting from the reaction of the amino group of anisotropine with methyl bromide.

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 25 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (96%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (96%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H400 (92%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P391, and P501

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3.4 Methods of Manufacturing: ESTERIFICATION OF TROPINE; WITH 2-PROPYLVALERYL CHLORIDE;, THEN QUATERNIZATION OF THE RESULTING ESTER WITH METHYL BROMIDE;.

3.5 Usage: Anisotropine Methylbromide is a antichloindergic agent and has been used for relief of gastrointestinal spasm and for the suppression of gastric acid secretion. Anisotropine Methylbromide was found to be potentially useful in the treatment of duodenal ulcer disease.

4. Safety and Handling

4.1 Exposure Standards and Regulations: Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

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4.2 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

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4.3 Formulations/Preparations: TABLETS: 10 MG; ELIXIR: 2 MG/ML, 10 MG.
VALPIN (TRADEMARK) 50-PB (ANISOTROPINE METHYLBROMIDE 50 MG WITH PHENOBARBITAL 15 MG).

4.4 Safety

Poison by subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of Br⁻ and NO_x

Hazard Codes : Harmful Xn, Dangerous N
Risk Statements :20/21/22-50/53
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements :36-61-60
S36:Wear suitable protective clothing.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S60:This material and its container must be disposed of as hazardous waste.

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4.5 Specification: Safety Statements:36-61-60
36:Wear suitable protective clothing
61:Avoid release to the environment. Refer to special instructions safety data sheet
60:This material and/or its container must be disposed of as hazardous waste

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4.6 Toxicity

1.	orl-rat LD50:705 mg/kg	NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),24.
2.	orl-mus LD50:850 mg/kg	NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),24.
3.	ipr-mus LD50:129 mg/kg	NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),24.
4.	scu-mus LD50:133 mg/kg	NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),24.
5.	ivn-mus LD50:6300 µg/kg	OYYAA2 Oyo Yakuri. Pharmacometrics. 2 (1968),70.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Acute toxicity - Inhalation, Category 4

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H312 Harmful in contact with skin H332 Harmful if inhaled H400 Very toxic to aquatic life
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/…if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/…if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Computed Properties

Molecular Weight：362.35g/mol
Molecular Formula：C₁₇H₃₂BrNO₂
Compound Is Canonicalized：True
XLogP3-AA：361.16164
Monoisotopic Mass：361.16164
Complexity：318
Rotatable Bond Count：7
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：3
Topological Polar Surface Area：26.3
Heavy Atom Count：：21
Defined Atom Stereocenter Count：2
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：2
CACTVS Substructure Key Fingerprint：AAADcfB6MAAAEAAAAAAAAAAAAAAAAWAAAAAsAAAABgAAAAAAAAAAHgAAAAAADTzhgAYCCAMABAAIAACQCAAAAAAAAAAAAAEIAAAAABIAgAAGAAAGAACAAAGYwCAOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

8.Other Information

Uses: Anisotropine Methylbromide is a antichloindergic agent and has been used for relief of gastrointestinal spasm and for the suppression of gastric acid secretion. Anisotropine Methylbromide was found to be potentially useful in the treatment of duodenal ulcer disease.

Definition: ChEBI: A quaternary ammonium salt resulting from the reaction of the amino group of anisotropine with methyl bromide.

Brand name: Valpin (Endo).

Originator: Valpin,Endo (Du Pont),US,1963

Manufacturing Process: Preparation of Di-n-propyl acetyl tropine hydrochloride: Tropine (11.12 grams) was dissolved in 100 ml of anhydrous pyridine and to this solution was added 15.64 grams of di-n-propyl acetyl chloride. The mixture was refluxed for 6 hours. This solution was then cooled and the pyridine removed in vacuum. The residue was dissolved in chloroform. The chloroform solution was washed with 10% hydrochloric acid to remove the residual trace of pyridine. The hydrochloride of the product ester is soluble in chloroform and is not extracted from chloroform by hydrochloric acid. This is an unexpected property.
The chloroform solution of the hydrochloride was dried over anhydrous calcium sulfate, and evaporated to dryness, leaving a semisolid residue of product ester hydrochloride. This was recrystallized from chloroform-hexane mixture, MP 186°C.
Preparation of the Anisotropine Methyl Bromide: To the acetone solution of the free base was added an acetone solution, containing an excess of methyl bromide. Within a few minutes the methobromide started to crystallize. The mixture was allowed to stand for several hours. The crystallized solid was filtered, and additional product was obtained by evaporation of the filtrate. The yield was nearly quantitative. After recrystallization from acetone, the product melted at 329°C.

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Therapeutic Function: Anticholinergic

用途: Octatropine methylbromide (INN) or anisotropine methylbromide (USAN), trade names Valpin, Endovalpin, Lytispasm and others, is a muscarinic antagonist and antispasmodic. It was introduced to the U.S. market in 1963 as an adjunct in the treatment of peptic ulcer, and promoted as being more specific to the gastrointestinal tract than other anticholinergics. Anisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide 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. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion.

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