2565-01-7

Basic information

• Product Name: (6aS)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline
• Synonyms: (S)-5,6,6a,7-Tetrahydro-1,2-dimethoxy-6-methyl-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinolin; 4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-6-methyl-, (6aS)-; 4H-Benzo[de][1,3]benzodioxolo[5,6-g]quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-6-methyl-, (S)-; 6a.alpha.-Aporphine, 1,2-dimethoxy-9,10-(methylenedioxy)-
• CAS NO: 2565-01-7
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.385
• Mol File: 2565-01-7.mol

Chemical Properties

• Boiling Point: 487.5°C at 760 mmHg
• Flash Point: 145.2°C
• Density: 1.266g/cm³
• Vapor Pressure: 1.18E-09mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: (6aS)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (6aS)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline(2565-01-7)
• EPA Substance Registry System: (6aS)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline(2565-01-7)

Safety Data

• Hazardous Substances Data: 2565-01-7(Hazardous Substances Data)

Usage

Uses

Due to the provided materials, there are no specific applications mentioned for (6aS)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline. However, given its complex structure and potential pharmacological and biological activities, it may be used in various industries upon further research and development. Possible applications could include:
Used in Pharmaceutical Industry:
(6aS)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline could be used as a pharmaceutical agent for [specific medical condition or treatment] due to its potential pharmacological properties.
Used in Chemical Research:
In the field of chemical research, (6aS)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline may serve as a subject for studying the effects of its functional groups and ring systems on its chemical behavior and potential interactions with other compounds.

Upstream product

• 42971-15-3 (+/-)-nantenine 

Relevant articles and documents

Synthetic studies and pharmacological evaluations on the MDMA ('Ecstasy') antagonist nantenine

The naturally occurring aporphine alkaloid nantenine, has been shown to antagonize behavioral and physiological effects of MDMA in mice. We have synthesized (±)-nantenine via an oxidative cyclization reaction with PIFA and evaluated its binding profile against a panel of CNS targets. To begin to understand the importance of the chiral center of nantenine with regards to its capacity to antagonize the effects of MDMA in vivo, (R)- and (S)-nantenine were prepared and evaluated in a food-reinforced operant task in rats. Pretreatment with either nantenine enantiomer (0.3 mg/kg ip) completely blocked the behavioral suppression induced upon administration of 3.0 mg/kg MDMA. (±)-Nantenine displayed high affinity and selectivity for the α1A adrenergic receptor among several other receptors suggesting that this α1 subtype may be significantly involved in the anti-MDMA effects of the enantiomers.

Evaluation of structural effects on 5-HT2A receptor antagonism by aporphines: Identification of a new aporphine with 5-HT2A antagonist activity

A set of aporphine analogs related to nantenine was evaluated for antagonist activity at 5-HT2A and α1A adrenergic receptors. With regards to 5-HT2A receptor antagonism, a C2 allyl group is detrimental to activity. The chiral center of nantenine is not important for 5-HT2A antagonist activity, however the N6 nitrogen atom is a critical feature for 5-HT2A antagonism. Compound 12b was the most potent 5-HT2A aporphine antagonist identified in this study and has similar potency to previously identified aporphine antagonists 2 and 3. The ring A and N6 modifications examined were detrimental to α1A antagonism. A slight eutomeric preference for the R enantiomer of nantenine was observed in relation to α1A antagonism.