111841-85-1

Basic information

• Product Name: abecarnil
• Synonyms: abecarnil;6-(Benzyloxy)-4-(methoxymethyl)-β-carboline-3-carboxylic acid isopropyl ester;6-Benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester;Abercanil;ZK-112119;ZK-112-119
• CAS NO: 111841-85-1
• Molecular Formula: C₂₄H₂₄N₂O₄
• Molecular Weight: 404.464
• Mol File: 111841-85-1.mol

Chemical Properties

• Melting Point: 150-151°
• Boiling Point: 620.2°Cat760mmHg
• Flash Point: 328.9°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 2.62E-15mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: abecarnil(CAS DataBase Reference)
• NIST Chemistry Reference: abecarnil(111841-85-1)
• EPA Substance Registry System: abecarnil(111841-85-1)

Safety Data

• Hazardous Substances Data: 111841-85-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Abecarnil is used as an anxiolytic agent for the treatment of generalized anxiety disorder. It acts as a full agonist at some receptors to provide potent anxiolytic effects and as a partial agonist at others to minimize side effects, such as dependency and abuse.
One clinical study compared abecarnil at different doses with a placebo in patients with generalized anxiety disorder, showing that abecarnil was significantly more effective than the placebo in terms of anxiolysis. Stopping treatment with lower doses of abecarnil did not produce withdrawal effects, although some effects were observed in patients taking higher doses.

Originator

Abecarnil,Schepa

Therapeutic Function

Anticonvulsant, Anxiolytic

Hazard

Human systemic effects.

InChI:InChI=1/C24H24N2O4/c1-15(2)30-24(27)23-19(14-28-3)22-18-11-17(29-13-16-7-5-4-6-8-16)9-10-20(18)26-21(22)12-25-23/h4-12,15,26H,13-14H2,1-3H3

Synthetic route

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

Conditions	Yield
With hydrogenchloride In isopropyl alcohol at 70℃; for 24h;	94%

6-Benzyloxy-4-methoxymethyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid isopropyl ester → abecarnil (111841-85-1)

Conditions	Yield
With trichloroisocyanuric acid; triethylamine for 16h; Ambient temperature; Yield given;

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

Conditions	Yield
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 View Scheme

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

Conditions	Yield
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 View Scheme

6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexylbromide + ethyl acetate n-hexane + abecarnil (111841-85-1) → 6-benzyloxy-4-methoxymethyl-9{6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexyl}9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

Conditions	Yield
With hydrogenchloride In tetrahydrofuran

abecarnil (111841-85-1) → 6-benzyloxy-4-methoxymethyl-β-carboline-3-carbaldehyde (122752-01-6)

Conditions	Yield
With sodium hydroxide; chloro-trimethyl-silane; triethylamine In ethanol; toluene

abecarnil (111841-85-1) → 6-benzyloxy-4-methoxymethyl-β-carboline-3-carbaldehyde oxime

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; chloro-trimethyl-silane; triethylamine / ethanol; toluene 2: potassium hydroxide; hydroxylamine hydrochloride / (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; N,N-dimethyl-formamide View Scheme

abecarnil (111841-85-1) → 6-Benzyloxy-3-(3-isoxazolyl)-4-methoxymethyl-β-carboline (122751-80-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; chloro-trimethyl-silane; triethylamine / ethanol; toluene 2: potassium hydroxide; hydroxylamine hydrochloride / (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; N,N-dimethyl-formamide 3: sodium hydroxide; N-Bromosuccinimide; triethylamine / N,N-dimethyl-formamide View Scheme

abecarnil (111841-85-1) → 6-benzyloxy-3-(5-ethoxy-3-isoxazolyl)-4-methoxymethyl-β-carboline (122751-81-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; chloro-trimethyl-silane; triethylamine / ethanol; toluene 2: potassium hydroxide; hydroxylamine hydrochloride / (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; N,N-dimethyl-formamide 3: N-Bromosuccinimide; triethylamine / N,N-dimethyl-formamide View Scheme

Upstream product

• 491595-78-9 isopropyl 4-methoxy-2-butynoate 

Downstream Products

• 122752-01-6 6-benzyloxy-4-methoxymethyl-β-carboline-3-carbaldehyde 

Relevant articles and documents

Synthesis of β- and γ-carbolines by the palladium-catalyzed iminoannulation of alkynes

A variety of substituted β- and γ-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting β-carboline alkaloids, ZK93423 and abecarnil (ZK112119).

A mild and efficient dehydrogenation method for 3-carboxy-1,2,3,4-tetrahydro-β-carbolines

A new mild and efficient method for the dehydrogenation of 3-carboxytetrahydro-β-carbolines using trichloroisocyanuric acid (TCCA) / triethylamine (TEA) has been developed.