6487-33-8

Basic information

• Product Name: (-)-isocorypalmine
• CAS NO: 6487-33-8
• Molecular Weight: 341.407
• Mol File: 6487-33-8.mol

Chemical Properties

• CAS DataBase Reference: (-)-isocorypalmine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-isocorypalmine(6487-33-8)
• EPA Substance Registry System: (-)-isocorypalmine(6487-33-8)

Safety Data

• Hazardous Substances Data: 6487-33-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(-)-Isocorypalmine is used as a potential therapeutic agent for the treatment of various medical conditions, including schizophrenia, addiction, and neurological disorders. Its interactions with serotonin and dopamine receptors make it a promising candidate for the development of novel drug compounds.
Used in Pain Management:
(-)-Isocorypalmine is used as a potential analgesic agent, with research suggesting that it may have pain-relieving effects. This makes it a candidate for the development of new pain management therapies.
Used in Anti-Inflammatory Applications:
(-)-Isocorypalmine has also been studied for its potential anti-inflammatory effects, which could lead to its use in the development of treatments for inflammatory conditions.
Further research is needed to fully understand the pharmacological properties and potential therapeutic uses of (-)-isocorypalmine, as well as to explore its potential applications in various industries.

Upstream product

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• 2934-97-6 (+/-)-tetrahydropalmatine 
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• 1198596-70-1 4-bromo-1-(ethoxymethoxy)-2-methoxybenzene 
• 1198596-71-2 methyl 3-(ethoxymethoxy)-2-methoxy-6-(2'-methoxy-2'-oxoethyl)benzoate 
• 27313-90-2 2-benzyloxy-3,9,10-trimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline 
• 605-34-5 (S)-scoulerine 
• 483-14-7 tetrahydropalmatine 
• 121-33-5 vanillin 
• 1422431-47-7 (S)-6-((7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2,3-dimethoxybenzyl acetate 
• 63909-38-6 3-methoxy-4-benzyloxy-ω-nitrostyrolene 
• 1422431-12-6 6-(2-(3,4-dimethoxyphenethylamino)-2-oxoethyl)-2,3-dimethoxyphenyl acetate 
• 1422431-15-9 (S)-6-((6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2,3-dimethoxylbenzyl acetate 
• 485-19-8 (+)-(S)-reticuline 

Downstream Products

• 518-90-1 3,4-dimethoxy-phthalic acid 
• 99866-19-0 4-ethoxy-5-methoxy-phthalic acid 
• 3621-36-1 columbamine 
• 483-14-7 tetrahydropalmatine 
• 522-97-4 canadine 

Relevant articles and documents

TETRAHYDROPROTOBERBERINE COMPOUND, PREPARATION METHOD THEREFOR AND USES THEREOF, AND PHARMACEUTICAL COMPOSITION

The present invention provides a tetrahydroprotoberberine compound represented by the formula (I), enantiomers, diastereomers, racemates and mixtures thereof, and pharmaceutically acceptable salts, crystalline hydrates and solvates thereof. The invention also provides a method for preparing the compound and the use thereof in the preparation of a medicament for preventing and/or treating central nervous system diseases.

Asymmetric total synthesis of tetrahydroprotoberberine derivatives and evaluation of their binding affinities at dopamine receptors

Cocaine addiction remains a serious challenge for clinical and medical research because there is no effective pharmacological treatment. L-THP, a natural product isolated from Corydalis yanhusuo W.T. Wang, is one of the most frequently used traditional herbs to treat drug addiction in China. Our laboratory first reported that its demethylated metabolites L-ICP, L-CD, and L-CP had high affinity at dopamine D1, D2, and D5 receptors. Here we report the chemical synthesis of these metabolites and other derivatives and their binding affinities at dopamine receptors. The synthesis of these bioactive metabolites will allow further in vivo study of their potential in treating cocaine addiction.

Tetrahydroprotoberberine alkaloids with dopamine and σ receptor affinity

Two series of analogues of the tetrahydroprotoberberine (THPB) alkaloid (±)-stepholidine that (a) contain various alkoxy substituents at the C10 position and, (b) were de-rigidified with respect to (±)-stepholidine, were synthesized and evaluated for affinity at dopamine and σ receptors in order to evaluate effects on D3 and σ2 receptor affinity and selectivity. Small n-alkoxy groups are best tolerated by D3 and σ2 receptors. Among all compounds tested, C10 methoxy and ethoxy analogues (10 and 11 respectively) displayed the highest affinity for σ2 receptors as well as σ2 versus σ1 selectivity and also showed the highest D3 receptor affinity. De-rigidification of stepholidine resulted in decreased affinity at all receptors evaluated; thus the tetracyclic THPB framework is advantageous for affinity at dopamine and σ receptors. Docking of the C10 analogues at the D3 receptor, suggest that an ionic interaction between the protonated nitrogen atom and Asp110, a H-bond interaction between the C2 phenol and Ser192, a H-bond interaction between the C10 phenol and Cys181 as well as hydrophobic interactions of the aryl rings to Phe106 and Phe345, are critical for high affinity of the compounds.

Tetrahydropalmatine derivative and preparation method and application thereof

The invention discloses a compound and a preparation method and application thereof. The compound is a compound shown in the formula I or stereisomer, geometric isomer, tautomer, nitrogen oxide, hydrate solvate, metabolite and pharmaceutically-acceptable salt or prodrug of the compound shown in the formula I. The compound is a tetrahydropalmatine derivative. The compound has the application in preparing medicine. The medicine can remarkably restrain proliferation of eucaryon tumor cells and/or treat or prevent tumors. The formula I is shown in the specification.

A divergent route to 9,10-oxygenated tetrahydroprotoberberine and 8-oxoprotoberberine alkaloids: Synthesis of (±)-isocorypalmine and oxypalmatine

A new route, which is germane to the synthesis of 9,10-oxygenated tetrahydroprotoberberines and 8-oxoprotoberberines is described. The route features the use of a diester (14) generated from reaction of dimethylmalonate with an aryl halide in the presence of n-butyllithium. The amide 17 prepared in subsequent steps is a versatile precursor for the synthesis of tetrahydroprotoberberine and 8-oxoprotoberberine scaffolds using standard high-yielding reactions. In this manner, (±)-isocorypalmine and oxypalmatine have been synthesized in 23% and 22% yields, respectively.

Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D1, D2 and serotonin 5-HT1A multi-action profile

An effective and rapid method for the microwave-assisted preparation of the key intermediate for the total synthesis of tetrahydroprotoberberines (THPBs) including l-stepholidine (l-SPD) was developed. Thirty-one THPB derivatives with diverse substituents on A and D ring were synthesized, and their binding affinity to dopamine D1, D2 and serotonin 5-HT 1A and 5-HT2A receptors were determined. Compounds 18k and 18m were identified as partial agonists at the D1 receptor with Ki values of 50 and 6.3 nM, while both compounds act as D2 receptor antagonists (Ki = 305 and 145 nM, respectively) and 5-HT1A receptor full agonists (Ki = 149 and 908 nM, respectively). These two THPBs compounds exerted antipsychotic actions in animal models. Further electrophysiological studies employing single-unit recording in intact animals demonstrated that 18k-excited dopaminergic (DA) neurons are associated with its 5-HT1A receptor agonistic activity. These results suggest that these two compounds targeted to multiple neurotransmitter receptors may present novel lead drugs with new pharmacological profiles for the treatment of schizophrenia.

Isoquinoline alkaloids isolated from Corydalis yanhusuo and their binding affinities at the dopamine D1 receptor

Bioactivity-guided fractionation of Corydalis yanhusuo has resulted in the isolation of eight known isoquinoline alkaloids - tetrahydropalmatine, isocorypalmine, stylopine, corydaline, columbamine, coptisin, 13-methylpalmatine, and dehydrocorybulbine. The

UNUSUAL METHYL TRANSFER IN THE BIOSYNTHESIS OF APORPHINE AND PROTOBERBERINE ALKALOIDS

(S)-Reticuline was triply-labelled with 13C and administrered to cell cultures of Peumus boldus and Berberis stolonifera, which are sources of aporphines and protoberberines, respectively.During incorporation of the labelled precursor into alkaloids of both groups, unexpected transmethylations of the methyl groups were observed by 13C NMR spectroscopy which seem to proceed via demethylation, flux of 13C through the C-1 pool, and remethylation. Key Word Index: Peumus boldus; Berberis stolonifera; Berberidaceae; cell suspension cultures; 13C NMR; reticuline; aporphines; protoberberines; alkaloids; biosynthesis

BERBERINE SYNTHASE, THE METHYLENEDIOXY GROUP FORMING ENZYME IN BERBERINE SYNTHESIS

An Fe(2+) containing enzyme responsible for the formation of the methylenedioxy group in berberine was discovered, purified to homogeneity and characterized; it acts on columbamine as a substrate rather than on (S)-tetrahydrocolumbamine as previously assumed.

ALKALOIDS OF Glaucium fimbrilligerum. II

The alkaloids of the epigeal part and roots of the plant Glaucium fimbrilligerum have been studied.A total of 18 alkaloids has been isolated, of which epiglaufidine proved to be new, and its structure has been established.Columbamine has been isolated from the genus Glaucium for the first time, and magnoflorine and stilopine α-hydroxymethylate from this species of plant for the first time.