Abecarnil

Base Information

• Chemical Name: Abecarnil
• CAS No.: 111841-85-1
• Molecular Formula: C24H24 N2 O4
• Molecular Weight: 404.466
• UNII: IZM1PNJ3JL
• DSSTox Substance ID: DTXSID40149745
• Nikkaji Number: J258.551K
• Wikipedia: Abecarnil
• Wikidata: Q4666461
• NCI Thesaurus Code: C76501
• Pharos Ligand ID: GWYRWLB4DDMZ
• ChEMBL ID: CHEMBL454095
• Mol file: 111841-85-1.mol

Synonyms:abecarnil;isopropyl 6-benzyloxy-4-methoxymethyl-beta-carboline-3-carboxylate;ZK 112119

Chemical Property of Abecarnil

Chemical Property:

• Vapor Pressure: 2.62E-15mmHg at 25°C
• Melting Point: 150-151°
• Boiling Point: 620.2°Cat760mmHg
• Flash Point: 328.9°C
• PSA: 73.44000
• Density: 1.246g/cm³
• LogP: 5.00670
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 404.17360725
• Heavy Atom Count: 30
• Complexity: 565

Purity/Quality:

98%,99%, ^*data from raw suppliers

Abecarnil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Human systemic effects.
• Hazard Codes: Human systemic effects.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)C1=NC=C2C(=C1COC)C3=C(N2)C=CC(=C3)OCC4=CC=CC=C4
• Description: Abecarnil is a β-carboline-3-carboxylic acid derivative that is in development for the treatment of anxiety disorders. Animal work has shown that abecarnil has a low propensity to cause the problems of dependency and abuse and that the drug has marked anxiolytic and anticonvulsant activity but does not appear to have significant effects on motor coordination—a finding in marked contrast to the effects of diazepam (Stephens et al. 1990). This interesting phenomena may be explained by the fact that abecarnil is acting as a full agonist at some receptors that mediate certain effects (potent anxiolytic) and as a partial agonist at others (lack of side effects). One published clinical study compared abecarnil at different doses with placebo in patients with generalized anxiety disorder (Ballenger et al. 1991). This showed that abecarnil was significantly more effective than placebo in terms of anxiolysis. Stopping treatment produced no withdrawal effects in patients on the lower dose, although some effects were seen in those taking higher doses.
• Uses: Abecarnil is a partial agonist at the benzodiazepine–GABA receptor complex, and is used in generalized anxiety disorder.
• Therapeutic Function: Anticonvulsant, Anxiolytic

Technology Process of Abecarnil

There total 5 articles about Abecarnil 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: 94.0%

isopropyl 6-benzyloxy-4,9-bis(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylate → abecarnil (111841-85-1)

Guidance literature:

With hydrogenchloride; In isopropyl alcohol; at 70 ℃; for 24h;

DOI:10.1021/jo026317u

Reference yield:

isopropyl 4-methoxy-2-butynoate (491595-78-9) → abecarnil (111841-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / Pd(OAc)2; PPh₃; n-Bu₃N / dimethylformamide / 100 °C

2: 94 percent / aq. HCl / propan-2-ol / 24 h / 70 °C

With hydrogenchloride; palladium diacetate; tributyl-amine; triphenylphosphine; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jo026317u

Reference yield:

5-benzyloxy-3-iodo-1-(methoxymethyl)indole-2-methylene-tertbutylamine → abecarnil (111841-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / Pd(OAc)2; PPh₃; n-Bu₃N / dimethylformamide / 100 °C

2: 94 percent / aq. HCl / propan-2-ol / 24 h / 70 °C

With hydrogenchloride; palladium diacetate; tributyl-amine; triphenylphosphine; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jo026317u

upstream raw materials:

isopropyl 4-methoxy-2-butynoate

Downstream raw materials:

6-benzyloxy-4-methoxymethyl-β-carboline-3-carbaldehyde

Refernces

• 1、 Haffer, Gregor,Nickisch, Klaus,Tilstam, Ulf. "A mild and efficient dehydrogenation method for 3-carboxy-1,2,3,4-tetrahydro-β-carbolines". . p. 993 - 998. Retrieved 1998.