6191-56-6

Basic information

• Product Name: 5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol diacetate
• Synonyms: 5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol diacetate;Diacetate (ester)
• CAS NO: 6191-56-6
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.4
• Mol File: 6191-56-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 127-128°
• Boiling Point: 501.9°C at 760 mmHg
• Flash Point: 257.3°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 3.34E-10mmHg at 25°C
• Refractive Index: 1.597
• PKA: 7.71±0.20(Predicted)
• CAS DataBase Reference: 5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol diacetate(6191-56-6)
• EPA Substance Registry System: 5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol diacetate(6191-56-6)

Safety Data

• Hazardous Substances Data: 6191-56-6(Hazardous Substances Data)

Usage

General Description

5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol diacetate is a chemical compound that belongs to the class of dibenzoquinolines. 5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol diacetate is a diacetate, meaning it contains two acetate groups. It is a derivative of tetrahydrodibenzoquinoline, which is a bicyclic compound with a quinoline backbone. The presence of the acetate groups suggests that it is often used as a prodrug, meaning that it can be metabolized in the body into an active form. 5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol diacetate may have biological activity and is often utilized in research and drug development due to its potential pharmacological properties.

InChI:InChI=1/C21H21NO4/c1-12(23)25-18-8-7-15-11-17-19-14(9-10-22(17)3)5-4-6-16(19)20(15)21(18)26-13(2)24/h4-8,17H,9-11H2,1-3H3/t17-/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 314-19-2 apomorphine hydrochloride 
• 58-00-4 apomorphin 
• 314-19-2 (±)-apomorphine hydrochloride 
• 110-86-1 pyridine 
• 58-00-4 5,6,6a,7-tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol 

Relevant articles and documents

Structure-Functional-Selectivity Relationship Studies of Novel Apomorphine Analogs to Develop D1R/D2R Biased Ligands

Loss of dopamine neurons is central to the manifestation of Parkinson's disease motor symptoms. The dopamine precursor L-DOPA, the most commonly used therapeutic agent for Parkinson's disease, can restore normal movement yet cause side-effects such as dyskinesias upon prolonged administration. Dopamine D1 and D2 receptors activate G-protein- A nd arrestin-dependent signaling pathways that regulate various dopamine-dependent functions including locomotion. Studies have shown that shifting the balance of dopamine receptor signaling toward the arrestin pathway can be beneficial for inducing normal movement, while reducing dyskinesias. However, simultaneous activation of both D1 and D2Rs is required for robust locomotor activity. Thus, it is desirable to develop ligands targeting both D1 and D2Rs and their functional selectivity. Here, we report structure-functional-selectivity relationship (SFSR) studies of novel apomorphine analogs to identify structural motifs responsible for biased activity at both D1 and D2Rs.

Racemization of (S)-(+)-10,11-dimethoxyaporphine and (S)-(+)-aporphine: efficient preparations of (R)-(-)-apomorphine and (R)-(-)-aporphine via a recycle process of resolution

Efficient preparations of (R)-(-)-apomorphine (R)-1 and (R)-(-)-aporphine (R)-2 based on a recycle process of resolution are described. In this recycle process of resolution, (RS)-(±)-10,11-dimethoxyaporphine 3 as the precursor of 1, and (RS)-(±)-aporphine 2 were successfully resolved into both enantiomers with (+)-dibenzoyltartaric acid (DBTA). The desired (R)-3 and (R)-2 were obtained and then, respectively, transformed to compound (R)-1, the hydrochloride salt of (R)-1, diacetate compound 4 and the hydrochloride salt of (R)-2; while the undesired (S)-3 and (S)-2 were racemized to obtain a racemate, which was suitable for further resolution. A method for the racemization of the undesired (S)-3 and (S)-2 was extensively studied, in order to obtain high-yielding racemization conditions. A plausible mechanism for the racemization of (S)-3 and (S)-2 was also proposed.

The acetylation of apomorphine. An improved method for the selective preparation of diacetylapomorphine utilizing trifluoroacetic acid/acetyl bromide

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