1-Methyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 1-Methyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 4965-09-7
• Molecular Formula: C10H13N
• Molecular Weight: 147.22
• Hs Code.: 2933990090
• European Community (EC) Number: 803-804-7
• DSSTox Substance ID: DTXSID70897161
• Nikkaji Number: J103.205D
• Wikidata: Q27215737
• ChEMBL ID: CHEMBL95456
• Mol file: 4965-09-7.mol

Synonyms:1-M-THIQ;1-methyl-1,2,3,4-tetrahydroisoquinoline;N-methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property of 1-Methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

• Vapor Pressure: 0.0404mmHg at 25°C
• Refractive Index: 1.522
• Boiling Point: 239.3 °C at 760 mmHg
• PKA: 9.73±0.40(Predicted)
• Flash Point: 100 °C
• PSA: 12.03000
• Density: 0.966 g/cm³
• LogP: 2.22210
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 147.104799419
• Heavy Atom Count: 11
• Complexity: 133

Purity/Quality:

99% ^*data from raw suppliers

1-Methyl-1,2,3,4-tetrahydroisoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=CC=CC=C2CCN1
• Uses: 1-Methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ) is an endogenous antidepressant and parkinsonism-preventing substance that demonstrates neuroprotectiveactivity. Following systemic administration in rats, 1-Methyl-1,2,3,4-tetrahydroisoquinoline produces antidepressant-like effect similar to the effect of imipramine. 1MeTIQ is a reversible short-acting moderate inhibitor of MAO A/B. Also known as 1,2,3,4-Tetrahydro-1-methylisoquinoline, 1MeTIQ. It is an important raw material and intermediate for revaprazan and pharmaceutical.

Technology Process of 1-Methyl-1,2,3,4-tetrahydroisoquinoline

There total 4 articles about 1-Methyl-1,2,3,4-tetrahydroisoquinoline 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: 29.0%

1-methyl-3,4,dihydroisoquinoline (2412-58-0) + 1-isopropyl-1,2,3,4-tetrahydroisoquinoline (77796-20-4,152971-88-5) → 1-methylisoquinoline (1721-93-3) + 1-(propan-2-yl)isoquinoline (20922-03-6) + 1-methyl-1,2,3,4-tetrahydroisoquinoline (4965-09-7)

Guidance literature:

With C₂₁H₂₁ClIrNO₂; In 2,2,2-trifluoroethanol; for 3h; Reflux; Inert atmosphere;

DOI:10.1002/anie.201300292

Reference yield: 18.0%

1-methyl-3,4,dihydroisoquinoline (2412-58-0) → 1-methylisoquinoline (1721-93-3) + 1-methyl-1,2,3,4-tetrahydroisoquinoline (4965-09-7)

Guidance literature:

With C₂₁H₂₁ClIrNO₂; In 2,2,2-trifluoroethanol; for 3h; Reflux; Inert atmosphere;

DOI:10.1002/anie.201300292

Reference yield:

(S)-1-methyl-1,2,3,4-tetrahydroisoquinoline (64982-61-2) → 1-methylisoquinoline (1721-93-3) + 1-methyl-1,2,3,4-tetrahydroisoquinoline (4965-09-7)

Guidance literature:

With [CpIrI₂]₂; In toluene; at 40 ℃;

DOI:10.1016/j.tetlet.2006.12.032

upstream raw materials:

(S)-1-methyl-1,2,3,4-tetrahydroisoquinoline

cyclopropanecarboxylic acid chloride

phenethylamine

1-methyl-3,4,dihydroisoquinoline

Downstream raw materials:

N-benzoyl-1-methyl-1,2,3,4-tetrahydroisoquinoline

1-methylisoquinoline

1-methyl-3,4,dihydroisoquinoline

hydrogen

Refernces

• 1、 Stirling, Matthew,Blacker, John,Page, Michael I.. "Chemoenzymatic dynamic kinetic resolution of secondary amines". . p. 1247 - 1250. Retrieved 2007/10/03.