Tetrahydropalmatine

Base Information

• Chemical Name: Tetrahydropalmatine
• CAS No.: 10097-84-4
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.434
• Hs Code.: 29339900
• Mol file: 10097-84-4.mol

Synonyms:Rotundine;5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo[a,g] quinolizine;

Chemical Property of Tetrahydropalmatine

Chemical Property:

• Appearance/Colour: light yellow powder crystal
• Vapor Pressure: 1.76E-09mmHg at 25°C
• Refractive Index: 1.608
• Boiling Point: 482.9 °C at 760 mmHg
• Flash Point: 138.7 °C
• PSA: 40.16000
• Density: 1.23 g/cm³
• LogP: 3.31440
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Tetrahydropalmatine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Tetrahydropalmatine (THP) is an isoquinoline alkaloid found in in several different plant species, mainly in the Corydalis genus (Yan Hu Suo), but also in other plants such as Stephania rotunda (Qian Jin Teng). These plants exhibits analgesic, antinociceptive, anxiolytic, antidepressant, and anti-parasitic activities, and have traditional uses in Chinese herbal medicine. In particular, the levo isomer of THP (l-THP) appears to contribute to many of the therapeutic effects of these herbs. Notably, the dextro isomer of THP has distinct pharmacological actions that include depletion of monoamines and may contribute to the toxicology profile of THP-containing preparations or racemic mixtures of the compound. In addition to serving as an active constituent in traditional Chinese herbal preparations, purified or synthetic l-THP is approved for use and available as Rotundine or Rotundin in China, where l-THP has been used as an analgesic and sedative for more than 40 years. The roots of Stephania rotunda furnish this alkaloid which forms colourless plates when crystallized from EtOH. It is laevorotatory with [α]23D - 262° (EtOH) and gives a crystalline hydrochloride with m.p. 258-9°C (dec.) and the methiodide which decomposes at that same temperature. Three methoxyl groups and one methyl group are present.
• Physical properties: Appearance: off-white solid, odorless, tasteless, and turns yellow under light and heat. It should be protected from light and air. Solubility: this product is usually dissolved in chloroform, slightly soluble in ethanol or ether, insoluble in water, and soluble in dilute sulfuric acid. Melting point: 141–144?°C. Specific optical rotation: ?290 to –300°.
• Uses: An analgesic drug found in Chinese herbal medicine, used to treat heart disease and liver damage.
• Clinical Use: 1. Pain induced by gastrointestinal and hepatobiliary disorders, menstrual pain, and pain after childbirth.2. Mild trauma and postoperative pain3. Headache insomnia and spasmodic cough.4. There is a report about the usage of Rotundine in arrhythmia caused by I–III hypertension and other diseases.5. The hypnotic effect of Rotundine happens in 15?min after administration and then appears after 2?h. Because the analgesic effect happens at the same time, Rotundine is particularly suitable for insomnia patients with pain.6. Side effects: drowsiness, dizziness, fatigue, and nausea. Large dose of Rotundine can inhibit the respiratory center and may cause extrapyramidal symptoms.

Technology Process of Tetrahydropalmatine

There total 37 articles about Tetrahydropalmatine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline (26067-60-7) → tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-1,1'-bis{(R)-4,5-dihydro-3H-dinaphtho[1,2-c:2',1'-e]-phosphepino}ferrocene; hydrogen; acetic acid; potassium bromide; In dichloromethane; at 25 ℃; for 72h; under 60804.1 Torr; enantioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.1c00602

Reference yield: 92.0%

(13aS)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizin-5-ol (870282-81-8) → tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 19h;

DOI:10.1021/jo051554t

Reference yield: 56.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1356336-76-9) → tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8)

Guidance literature:

formaldehyd; (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; With trifluoroacetic acid; In toluene; at 140 ℃; for 0.5h; Microwave irradiation;

With sodium hydroxide; In water; pH=8;

DOI:10.1016/j.tet.2011.11.046

upstream raw materials:

diazomethane

(-)-isocorypalmine

corypalmine

(+/-)-tetrahydropalmatine

Downstream raw materials:

(-)-isocorypalmine

(S)-scoulerine

(S)-(-)-8-oxoxylopinine

2,3,9,10-tetramethoxy-13aα-berbine; hydrochloride

Refernces

• 1、 Bhakuni, Dewan S.,Jain, Sudha,Gupta, Sandeep. "BIOSYNTHESIS OF (+)-, (-)- AND (+/-)-TETRAHYDROPALMATINES". . p. 1591 - 1594. Retrieved 1984.
• 2、 Chen, Fener,Chen, Wenchang,Chen, Yu,Jiang, Meifen,Li, Weijian,Tang, Pei,Yang, Zhi. "Total Synthesis of (-)-Canadine, (-)-Rotundine, (-)-Sinactine, and (-)-Xylopinine Using a Last-Step Enantioselective Ir-Catalyzed Hydrogenation". . p. 8143 - 8153. Retrieved 2021/06/28.
• 3、 Sun, Haifeng,Zhu, Liyuan,Yang, Huicui,Qian, Wangke,Guo, Lin,Zhou, Shengbin,Gao, Bo,Li, Zeng,Zhou, Yu,Jiang, Hualiang,Chen, Kaixian,Zhen, Xuechu,Liu, Hong. "Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D1, D2 and serotonin 5-HT1A multi-action profile". supporting information. p. 856 - 868. Retrieved 2013/03/13.