O-Methylpsychotrine

Base Information

• Chemical Name: O-Methylpsychotrine
• CAS No.: 523-01-3
• Molecular Formula: C29H38N2O4
• Molecular Weight: 478.632
• European Community (EC) Number: 208-339-8
• UNII: V7C64CD3BR
• DSSTox Substance ID: DTXSID70200318
• Nikkaji Number: J182.282I
• Wikidata: Q27155023
• Metabolomics Workbench ID: 137461
• ChEMBL ID: CHEMBL471812
• Mol file: 523-01-3.mol

Synonyms:O-methyl-psychotrine;O-methylpsychotrine;O-methylpsychotrine sulfate hepatahydrate

Chemical Property of O-Methylpsychotrine

Chemical Property:

• Boiling Point: 599.4°Cat760mmHg
• Flash Point: 316.3°C
• Density: 1.21g/cm³
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 478.28315770
• Heavy Atom Count: 35
• Complexity: 732

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4=NCCC5=CC(=C(C=C54)OC)OC)OC)OC
• Isomeric SMILES: CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1CC4=NCCC5=CC(=C(C=C54)OC)OC)OC)OC

Technology Process of O-Methylpsychotrine

There total 38 articles about O-Methylpsychotrine 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: 75.0%

2,3-(R,R)-11b-(S)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetamide (6110-83-4) → (-)-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-ylmethyl)-3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline (523-01-3)

Guidance literature:

With trichlorophosphate; In benzene; at 110 ℃; for 3.8h;

DOI:10.1021/ol0530326

Reference yield:

(S)-1-allyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (884337-44-4) → (-)-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-ylmethyl)-3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline (523-01-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 93 percent / second-generation Grubbs' catalyst / CH₂Cl₂ / 4 h / 60 °C

2.1: 96 percent / TMSOTf / CH₂Cl₂ / 20 °C

3.1: CH₂Cl₂ / 5 h / 20 °C

3.2: 84 percent / pyrrolidine / tetrahydrofuran / 20 °C

4.1: PhLi / tetrahydrofuran; hexane / 5 h

4.2: 57 percent / tetrahydrofuran

5.1: 87 percent / H₂ / Pd/C / methanol / 16 h / 20 °C

6.1: 73 percent / AlMe₃ / benzene / 10 h / 115 °C

7.1: 75 percent / POCl₃ / benzene / 3.8 h / 110 °C

With trimethylsilyl trifluoromethanesulfonate; hydrogen; trimethylaluminum; phenyllithium; trichlorophosphate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 4.1: Wittig reaction;

DOI:10.1021/ol0530326

Reference yield:

4-[(S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]but-2-enoic acid ethyl ester (884337-46-6) → (-)-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-ylmethyl)-3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline (523-01-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CH₂Cl₂ / 5 h / 20 °C

1.2: 84 percent / pyrrolidine / tetrahydrofuran / 20 °C

2.1: PhLi / tetrahydrofuran; hexane / 5 h

2.2: 57 percent / tetrahydrofuran

3.1: 87 percent / H₂ / Pd/C / methanol / 16 h / 20 °C

4.1: 73 percent / AlMe₃ / benzene / 10 h / 115 °C

5.1: 75 percent / POCl₃ / benzene / 3.8 h / 110 °C

With hydrogen; trimethylaluminum; phenyllithium; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 2.1: Wittig reaction;

DOI:10.1021/ol0530326

upstream raw materials:

2,3-(R,R)-11b-(S)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetamide

rac-10,11,6',7'-tetramethoxy-emet-1'-ene

(S)-1-allyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

4-[(S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]but-2-enoic acid ethyl ester

Downstream raw materials:

rac-10,11,6',7'-tetramethoxy-emetan-2'-carboxylic acid anilide

ent-10,11,6',7'-tetramethoxy-emetan-2'-carboxylic acid anilide

emetine