4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE

Product Name: 4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE
CAS No.: 90182-92-6
Chemical Name: 4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE
Synonyms: AHR-4965;AHR-4964;Zacopride;Zacoprida;Zacopridum;ZacoprideHCl;(S)-Zacopride;(R)-Zacopride;Zacopride [inn];Racemic zacopride
CBNumber: CB5279698
Molecular Formula: C15H20ClN3O2
Formula Weight: 309.79
MOL File: 90182-92-6.mol

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4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE Property

storage temp.: Desiccate at RT

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Tocris

Product number: 1795
Product name: Zacopridehydrochloride
Purity: ≥99%(HPLC)
Packaging: 10
Price: $154
Updated: 2021/12/16

Tocris

Product number: 1795
Product name: Zacopridehydrochloride
Purity: ≥99%(HPLC)
Packaging: 50
Price: $638
Updated: 2021/12/16

TRC

Product number: Z150703
Product name: Zacopride
Packaging: 25mg
Price: $220
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: BRS0000339
Product name: ZACOPRIDE
Purity: 95.00%
Packaging: 10MG
Price: $665.81
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: BRS0000339
Product name: ZACOPRIDE
Purity: 95.00%
Packaging: 50MG
Price: $1073.29
Updated: 2021/12/16

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4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE Chemical Properties,Usage,Production

Originator

Zacopride hydrochloride,ZYF Pharm Chemical

Uses

Anti-emetic; stimulant (peristaltic).

Uses

Zacopride is a highly potent SR-3 antagonist and SR-4 agonist. 5-HT3 receptor antagonist. Activates IK1 channel.

Definition

ChEBI: 4-amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2-methoxybenzamide is a member of benzamides.

Manufacturing Process

4-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide, fumarate [1:1]:
In a closed system equipped with an oil bubbler, 30 ml of tetrahydrofuran were added to a mixture of 4-amino-5-chloro-2-methoxybenzoic acid, 2.02 g (0.010 mole) and 1,1'-carbonyldiimidazole, 1.62 g (0.010 mole) with stirring. When evolution of carbon dioxide ceased, nitrogen was bubbled through the reaction mixture for 1 hr. A solution of 3-aminoquinuclidine, 1.26 g (0.010 mole) in 10 ml tetrahydrofuran was added dropwise to the stirred reaction mixture and stirring at room temperature continued for 3 hrs. TLC analysis (3% conc. ammonium hydroxide solution in methanol) showed some product formation. The mixture was heated at reflux temperature for 18 hours and then concentraded to an oil. TLC analysis showed the presence of the product, imidazole and 3-aminoquinuclidine. The oil was dissolved in methylene chloride (75 ml) and washed twice with 50 ml portions of aqueous sodium bicarbonate solution. The methylene chloride layer was dried over anhydrous magnesium sulfate and concentrated to yield 2.0 g (67%) of a glassy amorphous solid, the free base of the title compound.
In another reaction on a 0.020 mole scale, 5.18 g (83.8%) of the product as the free base was obtained.
The products were combined, dissolved in methanol (20 ml) and the solution and treated with a solution of fumaric acid (2.73 g) in methanol (50 ml). Absolute ether was added to precipitate the salt which was collected by filtration and recrystallized from methanol-water (200:20) with isopropyl ether added to the point of incipient cloudiness. The recrystallized salt (5.38 g) melted at 223°-225°C.
4-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide, hydrochloride, hydrate (1:1:1):
To an isopropyl alcohol solution of the above free base of the title compound is added in equal molar amount of 37% (conc.) hydrochloric acid. A salt is separated by addition of acetone followed by filtration which is recrystallized from acetone-water to give the title compound, MP: 158°-160°C.

Therapeutic Function

Antiemetic, Peristaltic stimulant

Biological Activity

Highly potent 5-HT 3 receptor antagonist (K i = 0.38 nM) and 5-HT 4 receptor agonist (K i = 373 nM). Antiemetic and anxiolytic following systemic administration in vivo .

4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE Suppliers

China 21 Germany 2 India 1 United Kingdom 1 United States 4 Global 29

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90182-92-6, 4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDERelated Search:

Mosapride QUINUCLIDINE Zacopride hydrochloride [USAN:INN] pancopride Mezacopride 4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE

4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE

ZACOPRIDE HYDROCHLORIDE

Zacopride

4-Amino-5-chloro-2-methoxy-N-(quinuclidin-3-yl)benzamide

4-Amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2-methoxybenzamide

(-)-4-Amino-5-chloro-2-methoxy-N-[(S)-quinuclidine-3β-yl]benzamide

(S)-Zacopride

4-Amino-5-chloro-2-methoxy-N-(quinuclidine-3β-yl)benzamide

4-Amino-N-[(3S)-1-azabicyclo[2.2.2]octa-3-yl]-5-chloro-2-methoxybenzamide

AHR-4965

(+)-4-Amino-5-chloro-2-methoxy-N-[(R)-quinuclidine-3α-yl]benzamide

(R)-Zacopride

4-Amino-N-[(3R)-1-azabicyclo[2.2.2]octa-3-yl]-5-chloro-2-methoxybenzamide

AHR-4964

4-Amino-N-1-azabicyclo(2.2.2)oct-3-yl-5-chloro-2-methoxybenzamide

Benzamide, 4-amino-N-1-azabicyclo(2.2.2)oct-3-yl-5-chloro-2-methoxy-

Zacoprida

Zacoprida [spanish]

Zacopride [inn]

Zacopridum

Zacopridum [latin]

ZacoprideHCl

4-aMino-5-chloro-2-Methoxy-N-(quinuclidin-3-yl)benzaMide hydrochloride

Racemic zacopride

90182-92-6

C15H20ClN3O2HCl

Serotonin receptor