Lysergamide

Base Information

• Chemical Name: Lysergamide
• CAS No.: 478-94-4
• Molecular Formula: C16H17N3O
• Molecular Weight: 267.33
• European Community (EC) Number: 207-524-0
• UNII: 073830XH10
• DSSTox Substance ID: DTXSID20893673
• Nikkaji Number: J6.152B
• Wikipedia: Ergine
• Wikidata: Q2041643
• Metabolomics Workbench ID: 53156
• ChEMBL ID: CHEMBL227213
• Mol file: 478-94-4.mol

Synonyms:9,10-didehydro-6-methylergoline-8 beta-carboxamide;lysergamide;lysergic acid amide

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Chemical Property of Lysergamide

Chemical Property:

• Vapor Pressure: 4.18E-13mmHg at 25°C
• Melting Point: >200°C (dec.)
• Refractive Index: 1.7210 (estimate)
• Boiling Point: 572.3°C at 760 mmHg
• PKA: 15.87±0.20(Predicted)
• Flash Point: 299.9°C
• PSA: 62.12000
• Density: 1.34g/cm³
• LogP: 2.16110
• Storage Temp.: Amber Vial, -20?C Freezer, Under Inert Atmosphere
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 267.137162174
• Heavy Atom Count: 20
• Complexity: 461

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)C(=O)N
• Isomeric SMILES: CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)N
• Uses: An alkaloid in abundance in tall fescue, resulted in vasoconstriction similar to that previously shown for the ergot alkaloids ergonovine and ergotamine.

Technology Process of Lysergamide

There total 6 articles about Lysergamide 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:

D-lysergic acid (82-58-6) → (+)-Lysergamide (478-94-4)

Guidance literature:

D-lysergic acid; With 1-hydroxy-7-aza-benzotriazole; 1,3-di-tert-butylcarbodiimide; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; at 20 ℃;

With trifluoroacetic acid; at 20 ℃; for 1h; Further stages.;

DOI:10.1021/jm060947x

Reference yield:

(+)-isolysergic acid amide (2889-26-1) → (+)-Lysergamide (478-94-4)

Guidance literature:

With potassium hydroxide;

DOI:10.1039/jr9360001440

Reference yield:

→ (+)-Lysergamide (478-94-4)

Guidance literature:

With sulfur trioxide-N,N-dimethylformamide complex; N,N-dimethyl-formamide; und anschliessendes Behandeln mit wss.NH₃;

upstream raw materials:

(+)-isolysergic acid amide

D-lysergic acid

(-)-isolysergic acid hydrazide

(+/-)-isolysergic acid hydrazide

Refernces