Harmaline

Base Information

• Chemical Name: Harmaline
• CAS No.: 304-21-2
• Molecular Formula: C13H14N2O
• Molecular Weight: 214.267
• Hs Code.: 2933990090
• European Community (EC) Number: 206-152-6
• NSC Number: 407285
• UNII: CN58I4TOET
• DSSTox Substance ID: DTXSID8041038
• Nikkaji Number: J11.607F
• Wikipedia: Harmaline
• Wikidata: Q135270,Q104252234
• Pharos Ligand ID: PZTG1483H3BH
• Metabolomics Workbench ID: 51608
• ChEMBL ID: CHEMBL340807
• Mol file: 304-21-2.mol

Synonyms:3H-Pyrido(3,4-b)indole, 4,9-dihydro-7-methoxy-1-methyl-;Dihydroharmine;Harmaline;Harmidine

Chemical Property of Harmaline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 232-234 °C
• Refractive Index: 1.647
• Boiling Point: 426.415 °C at 760 mmHg
• PKA: 4.2(at 25℃)
• Flash Point: 211.688 °C
• PSA: 37.38000
• Density: 1.257 g/cm³
• LogP: 1.97720
• Water Solubility.: Slightly soluble in water
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 214.110613074
• Heavy Atom Count: 16
• Complexity: 302

Purity/Quality:

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

Harmaline >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 25-20/21/22
• Safety Statements: 22-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NCCC2=C1NC3=C2C=CC(=C3)OC
• Uses: CNS stimulant, antiparkinsonian agent CNS stimulant; may act through NMDA receptors. Reversible inhibitor of MAO-A

Technology Process of Harmaline

There total 11 articles about Harmaline 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:

N-(2-(6-methoxy-1H-indol-3-yl)ethyl)acetamide (22375-73-1) → harmaline (304-21-2)

Guidance literature:

With phosphorus pentachloride; xylene;

Reference yield:

2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → harmaline (304-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous HCl

2: H₃PO₄

With hydrogenchloride; phosphoric acid;

DOI:10.1139/v59-272

Reference yield:

(7-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-methanol (106275-52-9) → harmaline (304-21-2)

Guidance literature:

With phosphoric acid;

DOI:10.1139/v59-272

upstream raw materials:

harmine

N-(2-(6-methoxy-1H-indol-3-yl)ethyl)acetamide

(7-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-methanol

ethanol

Downstream raw materials:

(CH₃OC₁₁H₇N₂CH₃)AuP(C₆H₅)3

(CH₃OC₁₁H₈N₂CH₃)*Au⁽¹⁺⁾*P(C₆H₅)3*{BF₄}^(1-)={(CH₃OC₁₁H₈N₂CH₃)AuP(C₆H₅)3}{BF₄}

harmine

7-methoxy-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-one

Refernces