Pirlindole hydrochloride

Base Information

• Chemical Name: Pirlindole hydrochloride
• CAS No.: 16154-78-2
• Molecular Formula: C15H18 N2 . Cl H
• Molecular Weight: 262.782
• Hs Code.: 2933990090
• European Community (EC) Number: 240-307-9
• UNII: Q89W8I397C
• Wikipedia: Pirlindole
• Wikidata: Q27287113
• ChEMBL ID: CHEMBL1470001
• Mol file: 16154-78-2.mol

Synonyms:1,10-trimethylene-8-methyl-1,2,3,4-tetrahydropyrazino(1,2-a)indole;pirlindol;pirlindole;pirlindole hydrochloride;pyrazidol;pyrlindole

Chemical Property of Pirlindole hydrochloride

Chemical Property:

• Vapor Pressure: 2.39E-07mmHg at 25°C
• Melting Point: 260-264℃
• Boiling Point: 422.6°Cat760mmHg
• Flash Point: 209.4°C
• PSA: 16.96000
• Density: 1.29g/cm³
• LogP: 4.06110
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 262.1236763
• Heavy Atom Count: 18
• Complexity: 303

Purity/Quality:

98%Min ^*data from raw suppliers

8-Methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino-[3,2,1-jk]carbazole hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)N3CCNC4C3=C2CCC4.Cl
• Recent EU Clinical Trials: STUDY TO EVALUATE THE PROPORTIONALITY OF 3 ORAL DOSES OF PIRLINDOLE IN HEALTHY VOLUNTEERS.
• General Description: 2,3,3a,4,5,6-Hexahydro-8-methyl-1H-pyrazino[3,2,1-jk]carbazole monohydrochloride (also known as Pirlindole hydrochloride or Pyrazidol) is a tricyclic compound with demonstrated psychotropic activity, particularly as an antidepressant. Its structure-activity relationship highlights the importance of the side chain, as modifications such as a propyl group at the 4-position reduce efficacy. While analogs of 2,3,3a,4,5,6-hexahydro-8-methyl-1H-pyrazino[3,2,1-jk]carbazole monohydrochloride exhibit similar antidepressant effects, they may also display increased toxicity, emphasizing the need for careful structural optimization in drug development.

Technology Process of Pirlindole hydrochloride

There total 9 articles about Pirlindole hydrochloride 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: 76.0%

5,6-dihydro-8-methyl-4H-pyrazino<3,2,1-j,k>carbazole hydrochloride (15932-34-0) → 2,3,3a,4,5,6-hexahydro-8-methyl-1H-pyrazino(3,2,1-jk)carbazole monohydrochloride (16154-78-2,145511-50-8,145511-51-9)

Guidance literature:

With sodium tetrahydroborate; 1.)15 deg C, 30 min 2.)80 deg C, 30 min;

DOI:10.1007/BF00505759

Reference yield: 68.4%

(2-Chloro-ethyl)-(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-amine (110951-52-5) → 2,3,3a,4,5,6-hexahydro-8-methyl-1H-pyrazino(3,2,1-jk)carbazole monohydrochloride (16154-78-2,145511-50-8,145511-51-9)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In benzene; for 5h; Ambient temperature;

DOI:10.1007/BF00764890

Reference yield:

8-Methyl-2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole; hydrochloride (73166-21-9) → 2,3,3a,4,5,6-hexahydro-8-methyl-1H-pyrazino(3,2,1-jk)carbazole monohydrochloride (16154-78-2,145511-50-8,145511-51-9)

Guidance literature:

Multi-step reaction with 3 steps

1: various solvent(s) / Heating

2: 75 percent / NaBH₄ / methanol; H₂O

3: H₂ / 10percent Pd/C

With sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In methanol; water;

DOI:10.1002/hlca.19980810307

upstream raw materials:

5,6-dihydro-8-methyl-4H-pyrazino<3,2,1-j,k>carbazole hydrochloride

(2-Chloro-ethyl)-(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-amine

8-Methyl-3-(1-phenyl-ethyl)-2,3,3a,4,5,6-hexahydro-1H-pyrazino[3,2,1-jk]carbazole

8-Methyl-2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole; hydrochloride

Downstream raw materials:

8-Methyl-2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole; hydrochloride

Refernces

SYNTHESIS AND PSYCHOTROPIC ACTIVITY OF PYRAZIDOLE ANALOGS

10.1007/BF00758834

The research focuses on the synthesis and psychotropic activity of pyrazidole analogs, specifically tricyclic derivatives of pyrazino[1,2-a]indoles. The purpose is to explore the relationship between the chemical structure of these compounds and their antidepressant activity, aiming to develop new antidepressants with potentially improved efficacy and selectivity. The study concludes that certain synthesized compounds, particularly IVa and IVb, exhibit significant psychotropic activity similar to pyrazidole, although they are slightly more toxic. Compounds with a propyl group in the 4 position (IVc and IVd) showed reduced activity. This suggests that the structure of the side chain significantly influences the biological activity of these compounds.

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