Xylopinine

Base Information

• Chemical Name: Xylopinine
• CAS No.: 523-02-4
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.434
• NSC Number: 17067
• DSSTox Substance ID: DTXSID101317459
• Nikkaji Number: J116.909B
• Wikidata: Q27108574
• Metabolomics Workbench ID: 68415
• ChEMBL ID: CHEMBL465824
• Mol file: 523-02-4.mol

Synonyms:2,3,10,11-tetramethoxy-5,6,13,13a-tetrahydro-8H- dibenzo(a,g)quinolizine;norcoralydine;norcoralydine hydrochloride;norcoralydine hydrochloride, (S)-isomer;norcoralydine, (+-)-isomer;norcoralydine, (R)-isomer

Chemical Property of Xylopinine

Chemical Property:

• Vapor Pressure: 3.12E-09mmHg at 25°C
• Boiling Point: 476.2°C at 760 mmHg
• Flash Point: 136.3°C
• PSA: 40.16000
• Density: 1.23g/cm³
• LogP: 3.31440
• 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

(S)-2,3,10,11-Tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C3CC4=CC(=C(C=C4CN3CCC2=C1)OC)OC)OC
• Isomeric SMILES: COC1=C(C=C2[C@@H]3CC4=CC(=C(C=C4CN3CCC2=C1)OC)OC)OC
• Uses: (-?)?-?Xylopinine is a natural plant alkaloid with adrenoceptor (AR) α2 inhibiting activity.

Technology Process of Xylopinine

There total 165 articles about Xylopinine 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%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Tetrahydropapaverine (13074-31-2) → 2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline (523-02-4,4216-86-8,6872-27-1,13407-95-9)

Guidance literature:

With acetic acid; at 100 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2020.152599

Reference yield: 80.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5,66820-84-6) → 2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline (523-02-4,4216-86-8,6872-27-1,13407-95-9)

Guidance literature:

In ethanol; water; at 20 ℃; for 8h;

DOI:10.1007/BF00758315

Reference yield: 78.0%

2-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]-6,7-dimethoxyisoquinolinium bromide → 2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline (523-02-4,4216-86-8,6872-27-1,13407-95-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In ethyl acetate; toluene; for 4h; Heating;

DOI:10.1021/ol006213a

upstream raw materials:

(6S,13aS)-2,3,10,11-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-6-carbonitrile

(-)-protoberberine

formaldehyd

S-(-)-Norlaudanosine

Downstream raw materials:

3-(2-vinyl-4,5-dimethoxyphenyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

(+/-)-O-methylcorytenchirine

pseudopalmatine

(+/-)-Xylopinin-trans-methiodid

Refernces

• 1、 Ngoc Tram Le Quang Thuan,Gardent. "-". . p. 86. Retrieved 1969.
• 2、 -. "COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING NASH, NAFLD, AND OBESITY". . . Retrieved 2021/04/10.
• 3、 -. "Method for synthesizing tetrahydroberberine and derivatives thereof". Paragraph 0106-0112. . Retrieved 2021/07/08.