442-51-3

Basic information

• Product Name: BANISTERINE MONOHYDRATE
• Synonyms: Harmine;1-Methyl-7-Methoxy-β-carboline;Hal base;Harmine(Banisterine);1-Methyl-7-methoxy-beta-carboline;4-b)indole,7-methoxy-1-methyl-9h-pyrido(;7-Methoxy-1-methyl-9H-beta-carboline;9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl-
• CAS NO: 442-51-3
• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 212.25
• EINECS: 207-131-4
• Product Categories: Signalling;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;reagent;standard substance;Inhibitors;Heterocyclic Compounds;Alkaloids;Biochemistry;Indole Alkaloids;Neurochemicals;Fluorescent;Heterocyclic
• Mol File: 442-51-3.mol

Chemical Properties

• Melting Point: 262-264 °C(lit.)
• Boiling Point: 352.09°C (rough estimate)
• Flash Point: 139.7 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.1128 (rough estimate)
• Vapor Pressure: 6.42E-07mmHg at 25°C
• Refractive Index: 1.6920 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Solubility Slightly soluble in water, ethanol, ether, chloroform
• PKA: 7.7(at 25℃)
• Water Solubility: Soluble in DMSO (100 mM), DMF (~1.5 mg/ml), ethanol (~1.5 mg/ml), and PBS (pH 7.2, ~0.25 mg/ml). Insoluble in water.
• Merck: 14,4616
• BRN: 178813
• CAS DataBase Reference: BANISTERINE MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: BANISTERINE MONOHYDRATE(442-51-3)
• EPA Substance Registry System: BANISTERINE MONOHYDRATE(442-51-3)

Safety Data

• Hazard Codes: Xn
• Statements: 25-36-20/21/22
• Safety Statements: 22-24/25-36/37-26-36
• RIDADR: 1544
• WGK Germany: 3
• RTECS: UV0175000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 442-51-3(Hazardous Substances Data)

Usage

Description

BANISTERINE MONOHYDRATE is a central nervous system stimulant that is isolated from the seeds of Peganum harmala L., a plant belonging to the Zygophyllaceae family. It is known for its ability to stimulate the central nervous system and has potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
BANISTERINE MONOHYDRATE is used as a CNS stimulant for its ability to stimulate the central nervous system and potentially treat conditions related to CNS dysfunction.
Used in Neurological Disorders:
BANISTERINE MONOHYDRATE is used as an antiparkinsonian agent for its potential to alleviate symptoms associated with Parkinson's disease, a progressive neurological disorder.
Used in Research and Development:
BANISTERINE MONOHYDRATE is used as a research compound for studying the effects of CNS stimulants on the central nervous system and their potential applications in treating various neurological conditions.

Purification Methods

Crystallise harmine from MeOH and sublime it in a vacuum. See hydrochloride below. [Beilstein 23 II 348, 23 III/IV 2702, 23/12 V 237.]

InChI:InChI=1/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3

Synthetic route

7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride (40959-16-8) → harmine (442-51-3)

Conditions	Yield
With 5 mol% Pd/C; lithium carbonate In ethanol at 150℃; for 0.166667h; Sealed tube; Microwave irradiation;	99%

tetrahydroharmine (486-93-1, 17019-01-1) → harmine (442-51-3)

Conditions	Yield
With sulfuric acid In 2,2,2-trifluoroethanol for 30h; Reflux;	91%
With 5%-palladium/activated carbon In toluene for 24h; Reflux;	72%
With water; palladium; maleic acid

7-methoxy-1-methyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole → harmine (442-51-3)

Conditions	Yield
Stage #1: 7-methoxy-1-methyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole In tetrahydrofuran at -78℃; for 2h; Stage #2: With oxygen In tetrahydrofuran at 20℃;	76%

harmaline (304-21-2) → harmine (442-51-3)

Conditions	Yield
With carbon dioxide; DBN; Eosin Y In dimethyl sulfoxide at 25 - 30℃; Irradiation;	71%
With hydrogenchloride; nitric acid
With sulfuric acid; permanganate(VII) ion

N,N-dimethyl acetamide (127-19-5) + 1-benzenesulfonyl-6-methoxy-3-vinyl-1H-indole (575433-20-4) → harmine (442-51-3)

Conditions	Yield
Stage #1: 1-benzenesulfonyl-6-methoxy-3-vinyl-1H-indole With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl acetamide In tetrahydrofuran at -78 - -10℃; Stage #3: With hydroxylamine hydrochloride; sodium acetate In 1,2-dichloro-benzene for 8h; Heating;	56%