26067-60-7

Basic information

• Product Name: Dihydropalmatine
• Synonyms: Dihydropalmatine
• CAS NO: 26067-60-7
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.41
• Mol File: 26067-60-7.mol

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 555.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.25±0.1 g/cm3(Predicted)
• PKA: 3.08±0.20(Predicted)
• CAS DataBase Reference: Dihydropalmatine(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydropalmatine(26067-60-7)
• EPA Substance Registry System: Dihydropalmatine(26067-60-7)

Safety Data

• Hazardous Substances Data: 26067-60-7(Hazardous Substances Data)

Usage

Uses

Used in Traditional Chinese Medicine:
Dihydropalmatine is used as a traditional medicine for treating various health conditions such as pain, inflammation, and anxiety due to its sedative and analgesic properties.
Used in Opioid Addiction Treatment:
Dihydropalmatine is used as a potential treatment for opioid addiction and withdrawal symptoms, as it can modulate dopamine and serotonin levels in the brain, helping to alleviate cravings and withdrawal symptoms.
Used in Neurological Disorder Treatment:
Dihydropalmatine is used as a potential therapeutic agent for neurological disorders such as Parkinson's disease and epilepsy, as it has shown promise in treating these conditions.
Used in Pharmaceutical Industry:
Dihydropalmatine is used as a pharmaceutical compound for the development of new drugs and therapies targeting pain, inflammation, anxiety, opioid addiction, and neurological disorders, due to its diverse pharmacological properties and potential therapeutic applications.

Upstream product

• 91106-61-5 3,4-dihydro-6,7-dimethoxy-1-(3,4-dimethoxybenzocyclobutenyl)isoquinoline hydrochloride 
• 113557-41-8 7,8-dimethoxy-2-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroisoquinolin-3-one 
• 47355-66-8 N-(2,3-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)ethan-1-amine 
• 109806-78-2 N-(2,3-dimethoxybenzylidene)-2-(3,4-dimethoxyphenyl)ethanamine 
• 113557-33-8 2-bromo-4,5-dimethoxy-N-(2,3-dimethoxybenzyl)phenethylamine 
• 113575-52-3 7,8-dimethoxy-2-(3,4-dimethoxybenzyl)-4-methylthio-1,2,3,4-tetrahydroisoquinolin-3-one 
• 113557-30-5 N-(3,4-dimethoxybenzyl)-N-(2,3-dimethoxyphenethyl)-α-(methylthio)acetamide 
• 113557-31-6 N-(3,4-dimethoxybenzyl)-N-(2,3-dimethoxyphenethyl)-α-(methylsulfinyl)acetamide 
• 113557-37-2 2-(2-bromo-4,5-dimethoxyphenethyl)-7,8-dimethoxy-4-methylthio-1,2,3,4-tetrahydroisoquinolin-3-one 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 75875-56-8 2-(2,3-Dimethoxy-benzyl)-1-(methanesulfinyl-methylsulfanyl-methyl)-6,7-dimethoxy-1,2-dihydro-isoquinoline 
• 3893-01-4 2,3-dimethoxybenzyl chloride 
• 54636-77-0 2,3-dimethoxybenzyl bromide 

Downstream Products

• 2934-97-6 (+/-)-tetrahydropalmatine 
• 4880-79-9 palmatine iodide 
• 483-14-7 tetrahydropalmatine 
• 19716-66-6 pseudopalmatine 
• 3486-67-7 palmatine 

Relevant articles and documents

Syntheses and structure-activity relationships on antibacterial and anti-ulcerative colitis properties of quaternary 13-substituted palmatines and 8-oxo-13-substituted dihydropalmatines

In this study, quaternary palmatine is used as a lead compound to design and synthesize derivatives to evaluate bioactivities, with twenty-seven compounds of four series being obtained. Antibacterial activity was examined by determining the minimal inhibi

Total Synthesis of (-)-Canadine, (-)-Rotundine, (-)-Sinactine, and (-)-Xylopinine Using a Last-Step Enantioselective Ir-Catalyzed Hydrogenation

A concise asymmetric total synthesis of a group of tetrahydroprotoberberine alkaloids, (-)-canadine, (-)-rotundine, (-)-sinactine, and (-)-xylopinine, has been accomplished in three steps from the commercially available corresponding disubstituted phenylethylamine and disubstituted benzaldehyde. Our synthesis toward these four alkaloids took advantage of the following strategy: In the first step, we achieved an efficient and sustainable synthesis of secondary amine hydrochlorides via a fully continuous flow; in the second step, we developed a Pictet-Spengler reaction/Friedel-Crafts hydroxyalkylation/dehydration cascade for the construction of the dihydroprotoberberine core structure (ABCD-ring); and in the last step, Ir-catalyzed enantioselective hydrogenation was employed for the introduction of the desired stereochemistry at the C-14 position in the tetrahydroprotoberberine alkaloids. This work significantly expedites the asymmetric synthesis of the entire tetrahydroprotoberberine alkaloid family as well as a more diverse set of structurally related non-natural analogues.

Method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on micro-reaction system

The invention provides a method for preparing 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline based on a micro-reaction system. A first solution and a second solution are introduced into a first micro-mixer through a feeding pump to be mixed; a mixture of an arylethylamine solution and an aryl aldehyde solution is pumped into a first fixed bed reactor through the first micro-mixer to be subjected to a dehydration condensation reaction; the mixture subjected to the dehydration condensation reaction is introduced into a second fixed bed reactor through a second micro-mixer for catalytic hydrogenation; the mixed material subjected to catalytic hydrogenation and a methanol solution of saturated hydrochloric acid are introduced into a micro-channel reactor through a third micro-mixer for a salt forming reaction, and vacuum concentration, pulping and purification are carried out to obtain secondary amine hydrochloride; and in the presence of acid, a dehydrating agent and an additive, the secondary amine hydrochloride and a glyoxal solution are subjected to Pictet-Spengler reaction and Friedel-Crafts hydroxyalkylation and dehydration cascade reaction, so as to obtain the 5, 8-dihydro-6H-isoquinoline [3, 2-alpha] isoquinoline compound.

Fibrauretine hydrazone derivative and its preparation and use

The invention relates to an acylhydrazone derivative of palmatine. The acylhydrazone derivative of palmatine is characterized by having a structural formula show in the specification. The invention also provides a preparation method and application of the acylhydrazone derivative. The preparation method is simple and has strong operability. Palmatine is used as raw material and subjected to structural modification, an acylhydrazone structure is introduced, and the target product, namely benzaldehyde tetrahydropalmatine acetylhydrazone which is an acylhydrazone derivative of palmatine can be finally synthesized by virtue of superposition of function groups. The acylhydrazone derivative of palmatine has the advantages of good activity, less side effects and good anti-bacterial effect.

A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps

A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.

Derivatives Of Protoberberine Biological Alkaloids And Use Of Same Inhibiting Ulcerative Colitis

Disclosed are derivatives of protoberberine biological alkaloids or physiologically acceptable salts thereof produced by means of a derivative reaction of a source material of biological alkaline quaternary ammonium salts of protoberberine alkaloids, a preparation method for same and pharmaceutical uses thereof. The derivatives of protoberberine biological alkaloids or the physiologically acceptable salts thereof show activity inhibiting ulcerative colitis and can be used in the preparation of drugs for same.

DERIVATIVES OF PROTOBERBERINE BIOLOGICAL ALKALOIDS AND USE OF SAME INHIBITING ULCERATIVE COLITIS

Disclosed are derivatives of protoberberine biological alkaloids or physiologically acceptable salts thereof produced by means of a derivative reaction of a source material of biological alkaline quaternary ammonium salts of protoberberine alkaloids, a preparation method for same and pharmaceutical uses thereof. The derivatives of protoberberine biological alkaloids or the physiologically acceptable salts thereof show activity inhibiting ulcerative colitis and can be used in the preparation of drugs for same.

13,13a-DIHYDROBERBERINE DERIVATIVES, THEIR PHARMACEUTICAL COMPOSITION AND USE

The present invention provides 13,13a-dihydroberberine derivatives or their physiologically acceptable salts represented by the following formula, pharmaceutical compositions comprising the same, and uses thereof. The 13,13a-dihydroberberine derivatives have an activity of promoting glucose absorption in muscle cells, and the whole animal tests show that the present compounds have effects on improving glucose-tolerance and insulin-resistance, facilitating weight loss, relieving fatty liver and the like. Thus, the present compounds can be used in treating diabetes mellitus, adiposity, fatty liver and complications thereof induced by insulin resistance.

Convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids

New and convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids through the same intermediates was developed. Acylation of the brominated benzylphenethylamine (13) with α- chloro-α-(methylthio)acetyl chloride, followed by cyclization with stannic chloride, furnished the key intermediates 4-methylthio-3- phenethylisoquinolin-3-ones (14), which were methylated to provide their methyl derivatives (17). Both isoquinolin-3-ones (14, 17) were easily transformed into protoberberine alkaloids (16) and their 13-methyl alkaloids (21) in good yield.

Syntheses of (+/-)-Tetrahydropalmatine and Spirobenzylisoquinolines by Thermolysis of Benzocyclobutene Derivatives

The tetrahydroprotoberberine alkaloid, (+/-)-tetrahydropalmatine (1) was synthesized by heating the 1-benzocyclobutenyl-3,4-dihydroisoquinoline (16), followed by reduction of the dehydro compound (20) with sodium borohydride.Ochotensine type spirobenzylis