BANISTERINE MONOHYDRATE CAS 442-51-3
BANISTERINE MONOHYDRATE 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: | 442-51-3 |
| MF: | C13H12N2O |
| MW: | 212.25 |
| EINECS: | 207-131-4 |
| Product Categories: | reagent;standard substance;Inhibitors;Signalling;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Fluorescent;Heterocyclic;Heterocyclic Compounds;Alkaloids;Biochemistry;Indole Alkaloids;Neurochemicals |
| Mol File: | 442-51-3.mol |
BANISTERINE MONOHYDRATE Chemical Properties
| Melting point | 262-264 °C(lit.) |
| Boiling point | 352.09°C (rough estimate) |
| density | 1.1128 (rough estimate) |
| refractive index | 1.6920 (estimate) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Solubility Slightly soluble in water, ethanol, ether, chloroform |
| pka | 7.7(at 25℃) |
| form | Crystalline Powder |
| color | White to off-white |
| PH Range | Blue 0 uorescence (7.2) to yellow 0 uorescence (8.9) |
| 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. |
| λmax | 241nm, 301nm, 336nm |
| Merck | 14,4616 |
| BRN | 178813 |
| Major Application | Inks, antitumor agents, inhibition of cell proliferation, blocking breast and prostate cancer cells, tracer for ductal pancreatic cancer, DNA binding properties, treatment of neoplasia, antioxidants, therapy of depression, antileishmanial agent, treatment of parkinsonism, antiAIDS agents, antihypoxia agents, drugs, treatment of dependency disorder, psychiatric and neurological illness, antibiotics, antimalarial agents |
| InChI | 1S/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 |
| InChIKey | BXNJHAXVSOCGBA-UHFFFAOYSA-N |
| SMILES | [nH]1c2c(c3c1cc(cc3)OC)ccnc2C |
| LogP | 3.560 |
| CAS DataBase Reference | 442-51-3(CAS DataBase Reference) |
| NIST Chemistry Reference | Harmine(442-51-3) |
Safety Information
| Hazard Codes | Xn |
| Risk 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 |
| HS Code | 29339900 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Flam. Liq. 2 STOT SE 1 |
| Chemical Properties | Off-White Solid |
| Uses | A CNS stimulant isolated from seeds of Peganum harmala L. Zygophyllaceae |
| Uses | antiparkinsonian, CNS stimulant |
| Uses | central nervous system stimulant |
| Definition | ChEBI: A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7. |
| General Description | The combination index (CI, serves as a quantitative indicator of pharmacological interactions) for harmaline/harmine and methylene blue/harmine was studied. |
| Biological Activity | Central nervous system stimulant. |
| Synthesis | 486-93-1 442-51-3 General procedure for the synthesis of 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole from camptothecin standard 002: 5 mmol of 6-methoxytryptamine was placed in a 100 mL round-bottomed flask, 50 mL of an aqueous solution containing 1 mL of concentrated hydrochloric acid was added, and the reaction was stirred at 30 °C until complete dissolution. Subsequently, 10 mmol of acetaldehyde was added and the reaction was continued for 1 hour. After completion of the reaction, the pH was adjusted to 8 with aqueous sodium bicarbonate, filtered and dried to obtain 1-methyl-7-methoxy-tetrahydro-β-carboline. The dried 1-methyl-7-methoxy-tetrahydro-β-carboline was transferred to another 100 mL round-bottom flask, 50 mL of toluene and 5% Pd/C catalyst were added, and the reaction was refluxed for 24 hours. At the end of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Finally, it was purified by recrystallization from acetone to give 1-methyl-7-methoxy-β-carboline (3.6 mmol, 72% yield). |
| storage | Store at RT |
| 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.] |
| References | [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 6983 - 6987 [2] Ross. Khim. Zh., 2013, vol. 125, # 27, p. 7121 - 7125,5 [3] Patent: CN104557916, 2017, B. Location in patent: Paragraph 0034-0036 [4] Chemische Berichte, 1930, vol. 63, p. 2245,2247 [5] Tetrahedron, 2002, vol. 58, # 31, p. 6185 - 6197 |
BANISTERINE MONOHYDRATE Preparation Products And Raw materials
| Raw materials | Acetic acid-->N,N-Dimethylformamide-->Phosphorus oxitrichloride-->Potassium hydroxide-->Ammonia-->Pyridine-->Piperidine-->Sodium sulfide-->Potassium dichromate-->Acetaldehyde-->Aluminium-nickel-->6-Methoxyindole-->Hydantoin |
| Preparation Products | HARMOL-->HARMALINE |
