methyl bromide
3-(2-cyclopentyl-2-hydroxy-2-phenylacetyloxy)-1-methylpyrrolidine
glycopyrronium bromide
Conditions | Yield |
---|---|
In butanone at 20℃; Cooling with ice; | 22% |
In acetonitrile at -10 - 20℃; for 12h; | 144 g |
In chloroform; acetonitrile at 20℃; for 72h; |
1-methyl-3-pyrrolidinol
2-cyclopentyl-2-hydroxy-2-phenylacetic acid
glycopyrronium bromide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / toluene / 0.5 h / 20 °C 1.2: 20 °C 2.1: butanone / 20 °C / Cooling with ice View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 60 °C 1.2: 3 h / 110 °C 2.1: sulfuric acid / tetrahydrofuran / 70 °C 3.1: palladium on activated charcoal; hydrogen / methanol / 3 h / 25 °C 4.1: acetonitrile / 12 h / -10 - 20 °C View Scheme |
glycopyrronium bromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid / tetrahydrofuran / 70 °C 2: palladium on activated charcoal; hydrogen / methanol / 3 h / 25 °C 3: acetonitrile / 12 h / -10 - 20 °C View Scheme |
phenylglyoxylyl chloride
glycopyrronium bromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 12.25 h / 0 - 25 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / 0 °C 3.1: acetonitrile; chloroform / 72 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 25 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / 0 °C 3.1: acetonitrile; chloroform / 72 h / 20 °C View Scheme |
1-methyl-3-pyrrolidinol
glycopyrronium bromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 25 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / 0 °C 3.1: acetonitrile; chloroform / 72 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 25 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / 0 °C 3.1: acetonitrile; chloroform / 72 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 10.33 h / 0 - 20 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / 0 °C 3.1: acetonitrile; chloroform / 72 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 12.25 h / 0 - 25 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / 0 °C 3.1: acetonitrile; chloroform / 72 h / 20 °C View Scheme |
glycopyrronium bromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 10.33 h / 0 - 20 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / 0 °C 3.1: acetonitrile; chloroform / 72 h / 20 °C View Scheme |
glycopyrronium bromide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 0.5 h / 0 °C 1.2: 0.5 h / 0 °C 2.1: acetonitrile; chloroform / 72 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 25 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 0.5 h / 0 °C 3.1: acetonitrile; chloroform / 72 h / 20 °C View Scheme |
glycopyrronium bromide
[(cyclopentyl-hydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium chloride
Conditions | Yield |
---|---|
With Amberlite IRA900 Cl In ethanol; water Product distribution / selectivity; | 94% |
Stage #1: glycopyrronium bromide With silver(I) acetate In methanol at 15 - 25℃; for 2h; Stage #2: With hydrogenchloride In ethyl acetate at 5 - 10℃; for 1h; | 72% |
glycopyrronium bromide
[(cyclopentyl-hydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium chloride
Conditions | Yield |
---|---|
With resin Amberlite IRA900 CI In ethanol; water | 94% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; | A 3.87 g B 92% |
glycopyrronium bromide
(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate mono(4-methylbenzenesulfonate)
Conditions | Yield |
---|---|
With dihydrogen peroxide; toluene-4-sulfonic acid In cyclohexane; cyclohexene at 25 - 30℃; for 12h; Reagent/catalyst; | 69.2% |
glycopyrronium bromide
Conditions | Yield |
---|---|
With sodium iodide In dichloromethane; water for 16h; |
silver benzoate
glycopyrronium bromide
3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-pyrrolidinium benzoate
Conditions | Yield |
---|---|
In water at 92℃; |
silver(I) 4-methylbenzenesulfonate
glycopyrronium bromide
(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate mono(4-methylbenzenesulfonate)
Conditions | Yield |
---|---|
In water at 40℃; Darkness; | |
In isopropyl alcohol at 20℃; Darkness; |
glycopyrronium bromide
Conditions | Yield |
---|---|
In 2-methyltetrahydrofuran |
Conditions | Yield |
---|---|
In water at 20℃; for 96h; Solvent; |
Conditions | Yield |
---|---|
With potassium hydroxide In 2-methyltetrahydrofuran; water for 0.5h; |
glycopyrronium bromide
toluene-4-sulfonic acid
(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate mono(4-methylbenzenesulfonate)
Conditions | Yield |
---|---|
With Aliquat 336; sodium hydroxide In dichloromethane; cyclohexane; water at 25 - 30℃; for 24h; Reagent/catalyst; Solvent; Concentration; |
sodium tosylate
glycopyrronium bromide
(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate mono(4-methylbenzenesulfonate)
Conditions | Yield |
---|---|
In water at 40 - 45℃; Green chemistry; Industrial scale; | 390 g |
Molecular Structure of Glycopyrrolate (CAS NO.596-51-0):
IUPAC Name: (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate bromide
Molecular Formula: C19H28BrNO3
Molecular Weight: 398.334520 g/mol
ACD/LogP: 0.38
of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 0.38
ACD/LogD (pH 7.4): 0.38
ACD/BCF (pH 5.5): 1.15
ACD/BCF (pH 7.4): 1.15
ACD/KOC (pH 5.5): 38.39
ACD/KOC (pH 7.4): 38.39
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 6
Polar Surface Area: 35.53Å2
EINECS: 209-887-0
Classification Code: Adjuvants, anesthesia; Anticholinergic; Central Nervous System Agents; Cholinergic Agents; Cholinergic Antagonists; Drug / Therapeutic Agent; Muscarinic antagonists; Neurotransmitter Agents; Reproductive Effect
InChI
InChI=1/C19H28NO3.BrH/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15;/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3;1H/q+1;/p-1
Smiles
C1([C@@](c2ccccc2)(C(O[C@@H]2C[N+](C)(C)CC2)=O)O)CCCC1.[BrH-]
1. | ipr-rat LD50:196 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 17 (1970),361. | ||
2. | scu-rat LD50:833 mg/kg | NIIRDN “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),349. | ||
3. | orl-mus LD50:570 mg/kg | JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. 2 (1960),523. | ||
4. | ipr-mus LD50:90 mg/kg | JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. 2 (1960),523. | ||
5. | scu-mus LD50:122 mg/kg | YKYUA6 Yakkyoku. Pharmacy. 26 (1975),741. | ||
6. | ivn-mus LD50:15 mg/kg | 29ZVAB Handbook of Analytical Toxicology ,Sunshine, I., ed.,Cleveland, OH.: Chemical Rubber Co.,1969,55. | ||
7. | orl-rbt LD50:2360 mg/kg | OYYAA2 Oyo Yakuri. Pharmacometrics. 7 (1973),627. | ||
8. | ivn-rbt LD50:29,100 µg/kg | OYYAA2 Oyo Yakuri. Pharmacometrics. 7 (1973),627. |
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NOx and Br−. See also BROMIDES.
Glycopyrrolate , with CAS number of 596-51-0, can be called 1,1-dimethyl-3-hydroxypyrrolidiniumbromidealpha-cyclopentylmandelate ; 1-methyl-3-pyrrolidylalpha-phenylcyclopentaneglycolatemethobromide ; ahr504;asecryl;gastrodyn ; glycopyrrolatebromide ; nodapton ; pyrrolidinium,1,1-dimethyl-3-hydroxy-, bromide, alpha-cyclopentylmandelate . Glycopyrrolate (CAS NO.596-51-0) has some side effects as a medicine such as fever, heat stroke in hot environments, dry mouth, difficulty urinating, headaches, diarrhea and constipation. Glycopyrrolate (CAS NO.596-51-0) is a medicine used for treating stomach ulcers, asthma, COPD and hyperhidrosis. It is also used to reduce excessive saliva. In anesthesia, glycopyrrolate injection can be used as a preoperative medication to reduce salivary, tracheobronchial, and pharyngeal secretions, as well as decreasing the acidity of gastric secretion. It is also used to prevent neostigmine's muscarinic effects in combination with neostigmine.
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