Pirlindole

Base Information

• Chemical Name: Pirlindole
• CAS No.: 60762-57-4
• Molecular Formula: C₁₅H₁₈N₂
• Molecular Weight: 226.321
• Hs Code.: 2933990090
• UNII: V39YPH45FZ
• DSSTox Substance ID: DTXSID8048230
• Nikkaji Number: J18.441A
• Wikipedia: Pirlindole
• Wikidata: Q4363248
• NCI Thesaurus Code: C66428
• Pharos Ligand ID: N276Z2D1USGZ
• Metabolomics Workbench ID: 152276
• ChEMBL ID: CHEMBL32350
• Mol file: 60762-57-4.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

Chemical Property:

• Appearance/Colour: WHITE SOLID
• Vapor Pressure: 2.39E-07mmHg at 25°C
• Boiling Point: 422.6 °C at 760 mmHg
• Flash Point: 209.4 °C
• PSA: 79.71000
• Density: 1.29 g/cm³
• LogP: 3.84390
• Storage Temp.: Store at RT
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 226.146998583
• Heavy Atom Count: 17
• Complexity: 303

Purity/Quality:

98%Min ^*data from raw suppliers

Pirlindole mesylate ^*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
• Recent EU Clinical Trials: STUDY TO EVALUATE THE PROPORTIONALITY OF 3 ORAL DOSES OF PIRLINDOLE IN HEALTHY VOLUNTEERS.
• Description: Pirlindole is a selective and reversible monoamine oxidase A (MAO-A) inhibitor (IC50s = 250 and 34.2 nM for rat brain and heart MAO-A, respectively). It is selective for MAO-A over MAO-B (Kis = 52,100 and 59,900 nM, for rat brain and heart MAO-B, respectively). In rats, it reverses the depressive-like effects induced by chronic mild stress (CMS), increases proliferation of hippocampal neural progenitor cells, and reverses dendritic atrophy in granule neurons. Pirlindole is also an inhibitor of enterovirus-D68 and coxsackievirus B3 (CV-B3), inhibiting the genome replication phase of CV-B3 infection with an EC50 value of 7.7 μM independent of MAO-A activity.
• Uses: Antidepressive;Monoamine oxidase inhibitor

Technology Process of Pirlindole

There total 6 articles about Pirlindole 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: 77.52%

8-methyl-2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole (75804-32-9) → pirlindole (60762-57-4,134721-45-2,134721-46-3,145165-49-7)

Guidance literature:

With methanol; sodium tetrahydroborate; at 20 ℃; for 4h;

Reference yield:

p-tolylhydrazine hydrochloride (637-60-5,35467-65-3) → pirlindole (60762-57-4,134721-45-2,134721-46-3,145165-49-7)

Guidance literature:

Multi-step reaction with 5 steps

1: acetic acid; hydrogenchloride / methanol; water / 24 h / 20 - 60 °C

2: methanol / 8 h / 40 °C

3: calcium carbonate; phosphorus pentachloride / toluene / 18 h / 0 °C

4: sodium carbonate / water; N,N-dimethyl-formamide / 16 h / 80 °C

5: sodium tetrahydroborate; methanol / 4 h / 20 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; phosphorus pentachloride; sodium carbonate; acetic acid; calcium carbonate; In methanol; water; N,N-dimethyl-formamide; toluene;

Reference yield:

6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one (3449-48-7,812649-03-9) → pirlindole (60762-57-4,134721-45-2,134721-46-3,145165-49-7)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol / 8 h / 40 °C

2: calcium carbonate; phosphorus pentachloride / toluene / 18 h / 0 °C

3: sodium carbonate / water; N,N-dimethyl-formamide / 16 h / 80 °C

4: sodium tetrahydroborate; methanol / 4 h / 20 °C

With methanol; sodium tetrahydroborate; phosphorus pentachloride; sodium carbonate; calcium carbonate; In methanol; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

p-tolylhydrazine hydrochloride

6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

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

cyclohexane-1,2-dione

Downstream raw materials:

3-ethyl-8-methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino[3,2,1-jk]carbazole

3-benzyl-8-methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino[3,2,1-jk]carbazole

methyl (2E)-3-{ethyl[2-(1-methoxy-6-methyl-1,2,3,4-tetrahydro-9H-carbazol-9-yl)ethyl]amino}acrylate

1-(3-ethyl-10-methyl-2,3,5a,6,7,8-hexahydro-1H-[1,4]diazocino[7,8,1-jk]carbazol-5-yl)ethanone

Refernces