16562-13-3

Basic information

• Product Name: L-SPD
• Synonyms: 3,9-dimethoxy-13a-alpha-berbine-2,10-diol;g)quinolizine-2,10-diol,5,8,13,13a-tetrahydro-3,9-dimethoxy-6h-dibenzo((;l-2,10-dihydroxy-3,9-dimethyloxytetrahydropseudoberberine;stepholidine;L-STEPHOLIDINE;L-STEPHOLIDINE, STEPHANIA INTERMEDICA;L-SPD;L-STEPHOLIDINE95%
• CAS NO: 16562-13-3
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.37
• Product Categories: Heterocyclic Compounds;Heterocycles;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 16562-13-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 120-1220C
• Boiling Point: 524 °C at 760 mmHg
• Flash Point: 270.7 °C
• Appearance: /
• Density: 1.37 g/cm³
• Vapor Pressure: 1.34E-11mmHg at 25°C
• Refractive Index: 1.679
• PKA: 9.97±0.20(Predicted)
• CAS DataBase Reference: L-SPD(CAS DataBase Reference)
• NIST Chemistry Reference: L-SPD(16562-13-3)
• EPA Substance Registry System: L-SPD(16562-13-3)

Safety Data

• Hazardous Substances Data: 16562-13-3(Hazardous Substances Data)

Usage

Description

A new alkaloid of the protoberberine group, this base occurs in Stephania giabra. The structure has been assigned on the basis of chemical and spectroscopic evidence.

Chemical Properties

Pink Solid

Uses

Different sources of media describe the Uses of 16562-13-3 differently. You can refer to the following data:
1. Agonist; antagonist
2. A tetrahydroprotoberberine agonist at dopamine D1 and antagonist at D2 receptors. dyskinesia which is produced by L-DOPA or medicine to treat schizophrenia. Antipsychotics.
3. A tetrahydroprotoberberine agonist at dopamine D1 and antagonist at D2 receptors. It is used for preventing or treating neural diseases. The neural diseases comprise parkinsonism, schizophrenia and dyskinesia which is produced by L-DOPA or medicine to treat schizophrenia. Antipsychotics.

References

Cava et ai., f. Org. Chern., 33,2785 (1968)

InChI:InChI=1/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1

Upstream product

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Related news

Design, synthesis and evaluation of benzo[a]thieno[3,2-g]quinolizines as novel L-SPD (cas 16562-13-3) derivatives possessing dopamine D1, D2 and serotonin 5-HT1A multiple action profiles08/11/2019

A novel scaffold derived from l-SPD with a substituted thiophene group in the D ring were designed, synthesized, and evaluated for their binding affinities at dopamine (D1, D2 and D3) and serotonin (5-HT1A and 5-HT2A) receptors. Most of the tetracyclic compounds exhibited higher affinities for D...detailed

Relevant articles and documents

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.

Optical isomerism levorotatory Japanese Stephania root pyridine alkali and its derivatives of the process for the preparation of

Provided is a compound as shown in general formula (I), wherein the definitions for the various substituents are as stated in the specification. Also provided are a method for preparing the compound, use of the compound in the preparation of L-stepholidine (L-SPD) compound, and intermediates in the preparation method.

Total synthesis of (S)-(-)-stepholidine using (S)-tert-butanesulfinylimine

A new synthetic strategy of (S)-(-)-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (S)-tert-butanesulfinylimine was used as the key step, which was complished in 94 % de and the main isomer was isolated in 52% yield. (S)-(-)-Stepholidine was prepared after another 5 steps, with an overall yield of 18.3% and > 98% ee. The Japan Institute of Heterocyclic Chemistry.