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

InChIKey

BXNJHAXVSOCGBA-UHFFFAOYSA-N

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

BANISTERINE MONOHYDRATE Usage And Synthesis

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

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(442-51-3)Related Product Information

• VERATRIDINE
• daurisoline
• menisdaurin
• Xanthiside
• HARMALOL
• 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one
• HARMALINE
• L-carnitine
• Icariin
• Evodiamine
• Vasicine
• 9H-PYRIDO[3,4-B]INDOLE
• HARMINE HYDROCHLORIDE
• BANISTERINE MONOHYDRATE
• 9-METHOXYCANTHIN-6-ONE
• 7-Methoxy-b-carboline-1-propionic acid
• BROMOHARMINE HBR
• HARMINE METHYL IODIDE