Lysergic Acid Hydrazide

Base Information

• Chemical Name: Lysergic Acid Hydrazide
• CAS No.: 5256-61-1
• Molecular Formula: C₁₆H₁₈N₄O
• Molecular Weight: 282.345
• DSSTox Substance ID: DTXSID00537381
• Wikidata: Q82412359
• Mol file: 5256-61-1.mol

Synonyms:Lysergic Acid Hydrazide;5256-61-1;(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carbohydrazide;SCHEMBL10354383;DTXSID00537381;AKOS015967158;(6aR,9R)-7-Methyl-4,6,6a,7,8,9-hexa;(8beta)-6-Methyl-9,10-didehydroergoline-8-carbohydrazide;(6Ar,9r)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid hydrazide

Chemical Property of Lysergic Acid Hydrazide

Chemical Property:

• PSA: 77.64000
• LogP: 2.50600
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 282.14806121
• Heavy Atom Count: 21
• Complexity: 477

Purity/Quality:

Lysergic acid hydrazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)C(=O)NN
• Isomeric SMILES: CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)NN
• Uses: Intermediate in the preparation of Lysergic Amide.

Technology Process of Lysergic Acid Hydrazide

There total 9 articles about Lysergic Acid Hydrazide 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: 50.0%

lysergic acid methyl ester (4579-64-0) → (+/-)-lysergic acid hydrazide (5256-60-0,5256-61-1,57765-79-4)

Guidance literature:

With hydrazine hydrate; at 140 ℃; for 0.333333h;

DOI:10.1016/j.bmcl.2007.12.030

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (+/-)-lysergic acid (82-58-6,478-95-5,6915-32-8,23953-76-6,68985-97-7,68985-98-8) → (+/-)-isolysergic acid hydrazide (5256-60-0,5256-61-1,57765-79-4)

Guidance literature:

With diethyl ether; benzene; und Erwaermen des erhaltenen Methylesters mit N₂H₄ in Methanol;

DOI:10.1021/ja01594a039

Reference yield:

→ (+/-)-isolysergic acid hydrazide (5256-60-0,5256-61-1,57765-79-4)

Guidance literature:

With hydrazine; at 130 - 140 ℃;

DOI:10.1002/hlca.19430260324

upstream raw materials:

6-methyl-9,10-didehydro-ergoline-8-carboxylic acid hydrazide

(-)-isolysergic acid hydrazide

diazomethane

(+/-)-lysergic acid

Downstream raw materials:

(-)-isolysergic acid amide

(-)-lysergic acid hydrazide

(+/-)-isolysergic acid hydrazide

(+/-)-isolysergic acid amide

Refernces