Tetrahydropalmatine

Base Information

• Chemical Name: Tetrahydropalmatine
• CAS No.: 483-14-7
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.434
• European Community (EC) Number: 811-160-3
• UNII: 3X69CO5I79
• DSSTox Substance ID: DTXSID701020650
• Nikkaji Number: J31.887F
• Wikipedia: Tetrahydropalmatine
• Wikidata: Q7706555
• Pharos Ligand ID: AHBHGPLPRKYB
• Metabolomics Workbench ID: 50546
• ChEMBL ID: CHEMBL487182
• Mol file: 483-14-7.mol

Synonyms:(+-)-isomer of tetrahydropalmatine;(R)-isomer;corydalis B of tetrahydropalmatine;(S)-isomer of tetrahydropalmatine;5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo(a,g)quinolizine;corydalis B;gindarin;HCl of tetrahydropalmatine;HCl(+-)-isomer of tetrahydropalmatine;HCl(R)-isomer of tetrahydropalmatine;HCl(S)-isomer of tetrahydropalmatine;levo-tetrahydropalmatine;rotundine;Rotundium;tetrahydropalmatine;tetrahydropalmitine

Chemical Property of Tetrahydropalmatine

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 141-143 °C
• Boiling Point: 482.9 °C at 760 mmHg
• PKA: 6.53±0.20(Predicted)
• Flash Point: 138.7 °C
• PSA: 40.16000
• Density: 1.23 g/cm³
• LogP: 3.31440
• Storage Temp.: Refrigerator
• Solubility.: insoluble in H2O; ≥16 mg/mL in DMSO; ≥2.95 mg/mL in EtOH with gentle warming and ultrasonic
• Water Solubility.: Soluble in chloroform
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 355.17835828
• Heavy Atom Count: 26
• Complexity: 475

Purity/Quality:

99% ^*data from raw suppliers

Rotundine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC
• Isomeric SMILES: COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC
• Recent ClinicalTrials: Treatment of Schizophrenia With L-tetrahydropalmatine (l-THP): a Novel Dopamine Antagonist With Anti-inflammatory and Antiprotozoal Activity
• Uses: Rotundine is an analgesic drug found in Chinese herbal medicine, used to treat heart disease and liver damage.

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:

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

(-)-isocorypalmine

(S)-(-)-8-oxoxylopinine

(S)-scoulerine

Refernces

• 1、 -. "Method for synthesizing tetrahydroberberine and derivatives thereof". Paragraph 0094-0099. . Retrieved 2021/07/08.
• 2、 Mastranzo, Virginia M.,Olivares Romero, José Luis,Yuste, Francisco,Ortiz, Benjamín,Sánchez-Obregón, Rubén,García Ruano, José L.. "Asymmetric synthesis of (S)-(-)-tetrahydropalmatine and (S)-(-)-canadine via a sulfinyl-directed Pictet-Spengler cyclization". experimental part. p. 1266 - 1271. Retrieved 2012/02/15.