2934-97-6

Basic information

• Product Name: ROTUNDINUM
• Synonyms: TETRAHYDROPALMATINE, L-;(S)-2,3,9,10-TETRAMETHOXY-5,8,13,13A-TETRAHYDRO-6H-ISOQUINO[3,2-A]ISOQUINOLINE;ROTUNDINUM;ROTUNDIN HYDRATE;AKOS 208-04;L-TETRAHYDROPALMATINE;DL-TETRAHYDROPALMATINE;Rotundine CP2000
• CAS NO: 2934-97-6
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.43
• Product Categories: Inhibitors
• Mol File: 2934-97-6.mol
• Article Data: 34

Chemical Properties

• Melting Point: 155℃
• Boiling Point: 482.9 °C at 760 mmHg
• Flash Point: 138.7 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 1.76E-09mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
• PKA: 6.53±0.20(Predicted)
• CAS DataBase Reference: ROTUNDINUM(CAS DataBase Reference)
• NIST Chemistry Reference: ROTUNDINUM(2934-97-6)
• EPA Substance Registry System: ROTUNDINUM(2934-97-6)

Safety Data

• Hazardous Substances Data: 2934-97-6(Hazardous Substances Data)

Usage

Description

Tetrahydropalmatine can be prepared from the total bases of tetrahydroxy berberine. Tetrahydropalmatine can be used to prepare palmatine. Palmatine has a broad-spectrum antibacterial effect, especially against Candida albicans. It can be used clinically to treat gynecological inflammation, bacillary dysentery, enteritis, respiratory and urinary tract infections, surgical infections, and conjunctivitis. Palmatine can also enhance the relaxation of the body's norepinephrine smooth muscle. Tetrahydropalmatine, an active component isolated from corydalis, acts through inhibition of amygdaloid release of dopamine to inhibit an epileptic attack in rats.

Uses

Different sources of media describe the Uses of 2934-97-6 differently. You can refer to the following data:
1. DL-Tetrahydropalmatine is the main active substance of the Chinese herb corydalis which induces hypotension and bradycardia in rats through the antagonism of striatal dopamine D2 receptor.
2. analgesic, hypnotic, papaverine-like

In vivo research

Tetrahydropalmatine (THP), an active component isolated from corydalis (a Chinese herbal medicine), possesses analgesic effects. Picrotoxin treatment alone has a significant effect on the following activity measure: there is an increase in horizontal motion time (HMT), vertical motion time (VMT), clockwise turnings (CT), anticlockwise turning (ACT) and a decrease in freezing time (FT). Tetrahydropalmatine treatment alone causes a decrease in HMT, VMT and total distance traveled (TDT), but an increase in FT. Pretreatment of rats with an i.p. dose of 10 mg/kg or 15 mg/kg of Tetrahydropalmatine significantly attenuates the Picrotoxin-induced enhancement in HMT, VMT, CT, ACT and TDT, as well as reduction in FT. Another 48 rats under urethane anesthesia are randomly divided into six groups, each of eight rats. The s.c. injection of Picrotoxin causes an increase in amygdaloid release of dopamine (DA), while i.p. injection of Tetrahydropalmatine at 10 mg/kg has an insignificant effect on amygdaloid release of DA. Again, the Picrotoxin-induced increase in amygdaloid release of DA is significantly attenuated by pretreatment with Tetrahydropalmatine. The Picrotoxin-induced augmented amygdaloid release of DA is almost completely abolished by pretreatment with Tetrahydropalmatine 30 min before s.c. injection of Picrotoxin.

Preparation

A. Berberine hydrochloride is ring-opened under the conditions of p-toluenesulfonic acid, xylene, and HCl at 70°C to obtain desmethylene berberine hydrochloride.B. Demethylene berberine hydrochloride is methyl etherified with potassium carbonate, methanol, and dimethyl sulfate at 40°C to obtain palmatine hydrochloride.C. Palmatine hydrochloride is racemized under the conditions of methanol and sodium borohydride to obtain tetrahydropalmatine.

InChI:InChI=1/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1

Upstream product

• 26067-60-7 2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline 
• 86639-32-9 (+/-)-1-bromotetrahydropalmatine 
• 75875-47-7 2-(2,3-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium bromide 
• 1699-51-0 laudanosine 
• 186581-53-3 diazomethane 
• 6487-33-8 (-)-isocorypalmine 
• 6018-39-9 corypalmine 
• 75875-52-4 2-(2,3-Dimethoxy-benzyl)-1-(methanesulfinyl-methylsulfanyl-methyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline 
• 75875-56-8 2-(2,3-Dimethoxy-benzyl)-1-(methanesulfinyl-methylsulfanyl-methyl)-6,7-dimethoxy-1,2-dihydro-isoquinoline 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 79809-15-7 N-<2-(3,4-dimethoxyphenyl)ethyl>(3,4-dimethoxy-2-hydroxymethyl)-phenylacetamide 
• 4697-59-0 7,8-dimethoxyisochroman-3-one 

Downstream Products

• 4880-79-9 palmatine iodide 
• 3520-14-7 (R)-(+)-tetrahydropalmatine 
• 483-14-7 tetrahydropalmatine 
• 77519-57-4 (S)-(-)-8-oxoxylopinine 
• 6487-33-8 (-)-isocorypalmine 
• 2506-20-9 2,3,9,10-tetramethoxy-13aα-berbine; hydrochloride 
• 605-34-5 (S)-scoulerine 
• 483-34-1 isocorypalmine 
• 84-38-8 L-tetrahydropalmatine 
• 84-38-8 D-tetrahydropalmatine 

Relevant articles and documents

SYNTHESIS AND SEDATIVE PROPERTIES OF dl-TETRAHYDROPALMATINE

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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.

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.

Asymmetric synthesis of (S)-(-)-tetrahydropalmatine and (S)-(-)-canadine via a sulfinyl-directed Pictet-Spengler cyclization

(S)-(-)-Tetrahydropalmatine 2 and (S)-(-)-canadine 4 were synthesized in three steps from (S)-6, in 33% and 34% overall yield, respectively. Thus, condensation of the (S)-(E)-sulfinylimines 10 and 11 with the carbanion derived from (S)-6 gave the tetrahydroisoquinolines 12 and 13, respectively, which upon TFA induced N-desulfinylation, and subsequent microwave assisted Pictet-Spengler cyclization effected both cyclization and C-desulfinylation producing (S)-(-)-tetrahydropalmatine 2 and (S)-(-)-canadine 4 in optically pure form.