Alpertine Chemical Properties

Melting point:

142.5-144 °C

Boiling point:

616.5±55.0 °C(Predicted)

Density 

1.195±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

Soluble in DMSO

pka

15.23±0.30(Predicted)

Alpertine Usage And Synthesis

Originator

Alpertine ,ZYF Pharm Chemical

Uses

Antipsychotic.

Definition

ChEBI: Alpertine is a member of piperazines.

Manufacturing Process

1-[2-(2-Carbethoxy-5,6-dimethoxy-3-indolyl)ethyl]-4-phenylpiperazine:
To a suspension of 23 g (1.0 mole) of sodium pellets in 800 ml of absolute ether was added 80 ml of a mixture of 86 g (1.0 mole) of γ-butyrolactone and 146 g (1.0 mole) of ethyl oxalate. The reaction mixture began to boil gently and was allowed to reflux spontaneously for two hours, after which time the remainder of the γ-butyrolactone and ethyl oxalate mixture was added cautiously. When addition was complete, the mixture was refluxed for one hour, allowed to stand overnight, and the ether removed in vacuo. The residue was mixed with ice, acidified with cold, dilute sulfuric acid, extracted with ether, and the ether extracts dried over sodium sulfate and taken to dryness. Distillation of the residue in vacuo at 0.05 mm afforded 98 g of α-ethoxalyl-γ- butyrolactone, collected between 110-126°C.
Forty grams (0.215 mole) of the latter were heated under reflux in 100 ml of 2 N sulfuric acid until the evolution of carbon dioxide ceased, giving a solution of α-keto-δ-valerolactone.
3,4-Dimethoxyphenylhydrazine hydrochloride (44 g, 0.22 mole) was dissolved in 300 ml of water, treated with a solution of 12.3 g (0.22 mole) of potassium hydroxide in 50 ml of water, and cooled. To this mixture was added the above described solution of α-keto-δ-valerolactone, and the pH of the mixture was adjusted to about 2 with 10% sodium hydroxide. The mixture was warmed on a hot plate for five minutes, allowed to cool, extracted with chloroform, and the extracts dried over magnesium sulfate and concentrated to dryness giving 66 g of crude hydrazone.
The latter was dissolved in 100 ml of absolute ethanol, the mixture acidified with 400 ml of saturated ethanolic hydrogen chloride, and a stream of hydrogen chloride gas was passed through the mixture causing the temperature to rise to 80°C. The solid which separated from the reaction mixture was collected after standing overnight, and washed with cold absolute ethanol to give 38 g of crude 2-carboxy-5,6 -dimethoxy-3-(2- hydroxyethyl)indole.
The latter was suspended in 300 ml of absolute ethanol and the solution saturated with anhydrous hydrogen chloride for one hour. The mixture was allowed to stand for two hours, and the solid which separated was collected and dried to give 24 g of 2-carbethoxy-5,6-dimethoxy-3-(2-chloroethyl)indole, M.P. 179-181°C.
The latter was added to 15 ml of 1-phenylpiperazine and the mixture heated at 140-160°C for one hour and twenty minutes. The cooled mixture was triturated with 100 ml of ether, filtered, and the ether filtrate concentrated to dryness. The residue was mixed with water and acetic acid, the pH adjusted to about 5.0, and the insoluble material was collected by filtration giving 5 g of crude product which was recrystallized from methanol to give 2.2 g of 1-[2- (2-carbethoxy-5,6-dimethoxy-3-indolyl)ethyl]-4-phenylpiperazine, M.P. 142.5- 144.0°C.

Therapeutic Function

Antipsychotic; Neuroleptic

Alpertine(27076-46-6)Related Product Information

• 5,6-DIMETHOXYINDOLE-2-CARBOXYLIC ACID
• Bufotenine
• Ethyl 5-hydroxyindole-2-carboxylate
• ETHYL 5-METHOXYINDOLE-2-CARBOXYLATE
• ETHYL 5,6-DIMETHOXYINDOLE-2-CARBOXYLATE
• 5-METHOXYINDOLE-2-CARBOXYLIC ACID
• 5-Hydroxyindole-2-carboxylic acid
• 5,6-DIHYDROXYINDOLE
• Alpertine
• 5,6-Dimethoxyindole
• N,N-Dimethyl-5-methoxytryptamine
• oxypertine
• 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
• 6-Hydroxyindole-2-carboxylic acid
• 5-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER
• 6-Methoxy-1H-indole-2-carboxylic acid ethyl ester
• 5-hydroxy-6-methoxyindole
• METHYL 6-METHOXY-1H-INDOLE-2-CARBOXYLATE