| Identification | More | [Name]
BANISTERINE MONOHYDRATE | [CAS]
442-51-3 | [Synonyms]
BANISTERINE MONOHYDRATE
HARMAN MONOHYDROCHLORIDE MONOHYDRATE
HARMINE MONOHYDRATE
TELEPATHINE MONOHYDRATE
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-
Garmin
Harmin
Leucoharmine
Telepathien
Telepathin
Yagein
Yageine
Yajeine
HARMINE FREE BASE
Harmine,98+%
PYRIDO(3,4-B)INDOLE,7-METHOXY-1-METHYL-
7-Methoxy-1-methyl-9H-pyrido[3,4-β]indole | [EINECS(EC#)]
207-131-4 | [Molecular Formula]
C12H13ClN2O | [MDL Number]
MFCD00150055 | [Molecular Weight]
236.7 | [MOL File]
442-51-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [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 | [form ]
Crystalline Powder | [pka]
7.7(at 25℃) | [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. | [Usage]
A CNS stimulant isolated from seeds of Peganum harmala L. Zygophyllaceae | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R25:Toxic if swallowed.
R36:Irritating to the eyes.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37:Wear suitable protective clothing and gloves .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
1544 | [WGK Germany ]
3
| [RTECS ]
UV0175000
| [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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]
harmine, also known as telepathine, is an alkaloid of the β-carboline family that regulates pparγ expression through inhibition of the wnt signaling pathway. it also selectively binds to mao-a and reversibly inhibits monoamine oxidase a (mao-a) but not the variant mao-b[3].harmine has a severe cytotoxicity in hepatoma cells and holds great promise as an oncologic drug for anticancer treatment[4].[1] smith b, medda f, gokhale v, et al. recent advances in thedesign, synthesis, and biologicalevaluation of selective dyrk1a inhibitors: a new avenue for a diseasemodifying treatment of alzheimer’s?[j]. acs chemical neuroscience, 2012, 3(11):857-72.[2] waki h, park k w, mitro n, et al. the small molecule harmine is an antidiabetic cell-type-specific regulator of ppargamma expression.[j]. cell metabolism, 2007, 5(5):357-370.[3] ginovart n, meyer j h, boovariwala a, et al. positron emission tomography quantification of |[lsqb]|11c|[rsqb]|-harmine binding to monoamine oxidase-a in the human brain[j]. journal of cerebral blood flow & metabolism official journal of the international society of cerebral blood flow & metabolism, 2006, 26(3):330-44.[4] zhang l, zhang f, zhang w, et al. harmine suppresses homologous recombination repair and inhibits proliferation of hepatoma cells[j]. cancer biology & therapy, 2015, 16(11):1585-1592. | [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 |
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