72150-17-5

Basic information

• Product Name: Eptazocine
• Synonyms: (-)-NIH 9614;(-)-ST 2121;1,6-Methano-1H-4-benzazonin-10-ol, 2,3,4,5,6,7-hexahydro-1,4-dimethyl-, hydrobromide, (1S)-;1,6-Methano-1H-4-benzazonin-10-ol, 2,3,4,5,6,7-hexahydro-1,4-dimethyl-, hydrobromide, (1S,6S)-;l-ST-2121;MCV 4169;ST 2121, (-)-;ST-2121
• CAS NO: 72150-17-5
• Molecular Formula: C15H22BrNO
• Molecular Weight: 312.25
• Mol File: 72150-17-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 353.6°C at 760 mmHg
• Flash Point: 166.3°C
• Appearance: /
• Vapor Pressure: 1.74E-05mmHg at 25°C
• CAS DataBase Reference: Eptazocine(CAS DataBase Reference)
• NIST Chemistry Reference: Eptazocine(72150-17-5)
• EPA Substance Registry System: Eptazocine(72150-17-5)

Safety Data

• Hazardous Substances Data: 72150-17-5(Hazardous Substances Data)

Usage

Description

Eptazocine hydrobromide, also known by the brand name Sedapain, is a centrally-acting analgesic that is primarily used in the management of post-operative and cancer pain. It exhibits a mixed agonist/antagonist profile in animal studies, with its analgesic activity being mediated through opiate receptors and catecholaminergic neurons.

Uses

Used in Pharmaceutical Industry:
Eptazocine is used as an analgesic agent for the management of post-operative and cancer pain. Its efficacy is attributed to its interaction with opiate receptors and catecholaminergic neurons, providing relief from severe pain.
Additionally, Eptazocine Hydrobromide (CAS# 72150-17-5) is used as a component in various pharmaceutical compounds to enhance skin penetration for opioid antagonists. This is due to the presence of fatty acid esters and glycerin fatty acid esters, which improve the drug's absorption through the skin.

Originator

Nichiiko (Japan)

InChI:InChI=1/C15H21NO.BrH/c1-15-5-6-16(2)10-11(9-15)7-12-3-4-13(17)8-14(12)15;/h3-4,8,11,17H,5-7,9-10H2,1-2H3;1H/t11-,15-;/m1./s1

Upstream product

• 74958-17-1 (-)-(1S,6S)-2,3,4,5,6,7-hexahydro-1,4-dimethyl-10-methoxy-1,6-methano-1H-4-benzoazonine 
• 151950-91-3 tert-Butyl-[2-(3-iodo-propyl)-5-methoxy-phenoxy]-dimethyl-silane 
• 122818-71-7 N-[2-((S)-7-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl]-N-methyl-acetamide 
• 151950-97-9 2-(tert-Butyl-dimethyl-silanyloxy)-1-[(Z)-6-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hex-4-enyl]-4-methoxy-benzene 
• 151950-92-4 Trifluoro-methanesulfonic acid 2-[(Z)-6-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hex-4-enyl]-5-methoxy-phenyl ester 
• 151951-05-2 ((S)-7-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetaldehyde 
• 63559-26-2 2-(p-methoxybenzyl)propane-1,3-diol 
• 824-94-2 p-methoxybenzyl chloride 
• 174417-66-4 (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate 
• 174417-68-6 Acetic acid (R)-3-cyano-2-(4-methoxy-benzyl)-propyl ester 
• 174417-67-5 Acetic acid (S)-2-methanesulfonyloxymethyl-3-(4-methoxy-phenyl)-propyl ester 
• 174417-69-7 (R)-dihydro-4-[(4-methoxyphenyl)methyl]-2(3H)-furanone 
• 174417-72-2 (R)-1-methyl-3-(p-methoxybenzyl)-5-oxo-2,3,4,5,6,7-hexahydro-1H-azepine 
• 174417-70-0 ethyl (R)-4-chloro-3-(p-methoxybenzyl)butylate 

Relevant articles and documents

A novel and practical asymmetric synthesis of eptazocine hydrobromide

In order to prepare eptazocine hydrobromide effectively, a novel, mild and practical asymmetric process was developed starting from 1-methyl-7-methoxy-2-tetralone under the catalysis of N-(p-trifluoromethylbenzyl)cinchonidinium bromide. The reaction conditions were optimized to obtain the product in excellent overall yield and purity.

Chiral resolution techinical method of etexastine hydrobromide

The invention discloses a chiral resolution techinical method of etexastine hydrobromide. The techinical method comprises the following steps: taking racemic eptazocine as an initial raw material to carry out esterification with phthalic anhydride to obtain an etexastine carboxylic acid derivative, then carrying out salifying with a chiral phenylethylamine derivative for resolution to obtain a chiral intermediate, carrying out dissociating to remove chirality, carrying out degreasing to remove phthalic acid to obtain chiral eptazocine, adding hydrobromic acid for saltifying, and carrying out precipitating in an ethanol system to obtain the target product etexastine hydrobromide. According to the invention, the final compound is adopted for resolution, and resolution of an intermediate is avoided, so that the use of a highly toxic product ethyl chloroformate is greatly reduced, high-temperature high-pressure distillation operation is reduced, and the method is beneficial for productionpersonnel and the environment. The addition amount of the hydrobromic acid is 1.5 times of equivalent weight of the substrate, ethanol is used as a solvent system, and concentration is not needed after the acid is added, so that damage to the product by high temperature is avoided, impurities generated due to the fact that the target object is degraded at the high temperature is reduced, and colorof the product can be improved.

A hydrobromidum eptazocine preparation method

The invention provides a method for preparing eptazocine hydrobromide. The method comprises the following steps: enabling a compound II, namely (1S,6S)-(-)-1,4-dimethyl-10-methoxy group-2,3,4,5,6,7-hexahydrogen-1,6-methylene-1H-4-benzo nonylbenzene to react in a hydrogen bromide solution, after reaction, drying reaction liquid by distillation at reduced pressure, drying by distillation at reduced pressure by adding water for multiple times and performing recrystallization refining for multiple times, and adding a certain amount of HBr solution during refining at the last time. The product color is qualified, the product is colorless and transparent after being dissolved in water, and the purity achieves more than 99.8 percent.