Amsonin

Base Information

• Chemical Name: Amsonin
• CAS No.: 549-84-8
• Molecular Formula: C21H26N2O3
• Molecular Weight: 354.449
• European Community (EC) Number: 208-977-7
• UNII: 3O5A4HTP2B
• DSSTox Substance ID: DTXSID701319089
• Nikkaji Number: J16.157H
• Wikidata: Q104938010
• Pharos Ligand ID: GL64Q4C7X68V
• Metabolomics Workbench ID: 126760
• ChEMBL ID: CHEMBL2079555
• Mol file: 549-84-8.mol

Synonyms:beta-Yohimbine;549-84-8;Amsonin;Amsonine;beta-Yohimbin;3O5A4HTP2B;CHEMBL2079555;EINECS 208-977-7;NSC 93133;Methyl (16alpha,17beta)-17-hydroxyyohimban-16-carboxylate;methyl (1S,15R,18R,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;-Yohimbine;NSC-93133;(-)-beta-Yohimbine;.BETA.-YOHIMBIN;UNII-3O5A4HTP2B;SCHEMBL564078;Yohimban-16-alpha-carboxylic acid, 17-beta-hydroxy-, methyl ester;Yohimban-16alpha-carboxylic acid, 17beta-hydroxy-, methyl ester;(-)-.BETA.-YOHIMBINE;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17beta)-;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16-alpha,17-beta)-;DTXSID701319089;BDBM50407152;AKOS040761411;.BETA.-YOHIMBINE [EP IMPURITY];A855796;YOHIMBINE HYDROCHLORIDE IMPURITY A [EP IMPURITY];(-)--Yohimbine;-Yohimbin;METHYL 17.BETA.-HYDROXYYOHIMBAN-16.ALPHA.-CARBOXYLATE;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16.alpha.,17.beta.)-;Methyl (1R,15R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

Chemical Property of Amsonin

Chemical Property:

• Boiling Point: 543 °C at 760 mmHg
• Flash Point: 282.2 °C
• PSA: 65.56000
• Density: 1.31 g/cm³
• LogP: 2.58500
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 354.19434270
• Heavy Atom Count: 26
• Complexity: 555

Purity/Quality:

99%, ^*data from raw suppliers

β-Yohimbine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• Isomeric SMILES: COC(=O)[C@H]1[C@@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O

Technology Process of Amsonin

There total 63 articles about Amsonin 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: 74.0%

(+)-yohimbinone (2671-57-0) → β-yohimbine (549-84-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 1.5h; Ambient temperature;

DOI:10.1021/ja00099a019

Reference yield:

18,19-didehydroyohimban-17-one (54725-64-3) → β-yohimbine (549-84-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1.5 h

2: 97 percent / H₂ / 10percent Pd/C / methanol / 0.25 h / 760 Torr / Ambient temperature

3: 82 percent / K₂CO₃, MeOH / 8 h / Ambient temperature

4: 74 percent / NaBH₄ / methanol / 1.5 h / Ambient temperature

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; hydrogen; potassium carbonate; lithium diisopropyl amide; palladium on activated charcoal; In methanol;

DOI:10.1021/ja00099a019

Reference yield:

17β-hydroxy-18,19-didehydroyohimbane (158146-68-0) → β-yohimbine (549-84-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / N-methylmorpholine N-oxide, 4A molecular sieves, tetra-n-propylammonium perruthenate / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 1.) LDA, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1.5 h

3: 97 percent / H₂ / 10percent Pd/C / methanol / 0.25 h / 760 Torr / Ambient temperature

4: 82 percent / K₂CO₃, MeOH / 8 h / Ambient temperature

5: 74 percent / NaBH₄ / methanol / 1.5 h / Ambient temperature

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; potassium carbonate; 4-methylmorpholine N-oxide; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja00099a019

upstream raw materials:

Yohimbine

17β-methoxy-yohimban-16α-carboxylic acid methyl ester

17β-acetoxy-yohimban-16α-carboxylic acid

(-)-Δ^15,16-didehydroyohimbinone

Downstream raw materials:

Yohimbine

(+)-yohimbinone

Refernces

• 1、 Brown, Richard T.,Pratt, Simon B.,Richards, Paul. "Enantiospecific synthesis of (-)-3-iso-19,20-dehydro-β-yohimbine from secologanin: A route to normal and pseudo stereoisomers of yohimbine". . p. 5627 - 5630. Retrieved 2007/10/03.
• 2、 Kuehne, Martin E.,Muth, Randy S.. "Total Syntheses of Yohimbe Alkaloids, with Stereoselection for the Normal, Allo, and 3-Epiallo Series, Based on Annelations of 4-Methoxy-1,2-dihydropyridones". . p. 2701 - 2712. Retrieved 2007/10/02.