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| CAS No.: | 442-51-3 |
|---|---|
| Name: | BANISTERINE MONOHYDRATE |
| Article Data: | 31 |
| Molecular Structure: | |
|
|
|
| Formula: | C13H12N2O |
| Molecular Weight: | 212.251 |
| Synonyms: | 1-Methyl-7-methoxy-b-carboline;7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole;Banisterin;Banisterine;Harmin;Leucoharmine;Telepathin;Telepathine;Yagein;Yageine; |
| EINECS: | 207-131-4 |
| Density: | 1.252 g/cm3 |
| Melting Point: | 262-264 °C(lit.) |
| Boiling Point: | 421.4 °C at 760 mmHg |
| Flash Point: | 139.7 °C |
| 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. |
| Appearance: | Off-white solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 25-36-20/21/22 |
| Safety: | 22-24/25-36/37-26-36 |
| Transport Information: | UN 1544 |
| PSA: | 37.91000 |
| LogP: | 3.03310 |
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7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride
- 442-51-3
harmine
| Conditions | Yield |
|---|---|
| With 5 mol% Pd/C; lithium carbonate In ethanol at 150℃; for 0.166667h; Sealed tube; Microwave irradiation; | 99% |
- 486-93-1, 17019-01-1
tetrahydroharmine
- 442-51-3
harmine
| 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 |
- 442-51-3
harmine
| 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% |
| 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 |
- 127-19-5
N,N-dimethyl acetamide
- 575433-20-4
1-benzenesulfonyl-6-methoxy-3-vinyl-1H-indole
- 442-51-3
harmine
| 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% |
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Chemistry
IUPAC Name: 7-Methoxy-1-methyl-9H-pyrido[3,4-B]indole
The MF of Banisterine monohydrate (CAS NO.442-51-3) is C12H13ClN2O.
The MW of Banisterine monohydrate (CAS NO.442-51-3) is 236.7.
Synonyms of Banisterine monohydrate (CAS NO.442-51-3): 1-Methyl-7-methoxy-beta-carboline ; 4-B)Indole,7-methoxy-1-methyl-9h-pyrido( ; 7-Methoxy-1-methyl-9H-beta-carboline ; Harmin ; Leucoharmine ; Telepathien ; 9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl- ; Garmin
Product Categories: Heterocyclic Compounds;Alkaloids;Biochemistry;Indole Alkaloids
Apperance: Off-White Solid
Index of Refraction: 1.706
EINECS: 207-131-4
Density: 1.252 g/ml
Flash Point: 139.7 °C
Boiling Point: 421.4 °C
Melting Point: 262-266 °C
Merck: 14,4616
BRN: 178813
Uses
Banisterine monohydrate (CAS NO.442-51-3) is a CNS stimulant isolated from seeds of Peganum harmala L. Zygophyllaceae.As an MAO inhibitor, harmine inhibits the breakdown of monoamines by enzymes called monoamine oxidases.Harmine is also a useful fluorescent pH indicator. As the pH of its local environment increases, the fluorescence emission of harmine decreases.
Production
Raw materials: Acetic acid glacial-->N,N-Dimethylformamide-->Phosphorus oxychloride-->Potassium hydroxide -->Ammonia-->Azabenzene-->1-Oxa-4-azacyclohexane-->Sodium sulfide-->Potassium dichromate-->Acetaldehyde-->Aluminium-nickel-->6-Methoxyindole-->Hydantoin
Toxicity Data With Reference
| 1. | ims-man TDLo:3 mg/kg:CNS,GIT | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133. | ||
| 2. | scu-mus LD50:243 mg/kg | PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. 10 (1976),1171. | ||
| 3. | ivn-mus LDLo:50 mg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133. | ||
| 4. | ivn-rat LDLo:10 mg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133. | ||
| 5. | scu-rbt LDLo:200 mg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133. | ||
| 6. | ivn-rbt LDLo:60 mg/kg | NEPHBW Neuropharmacology. 10 (1971),15. | ||
| 7. | scu-gpg LDLo:100 mg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133. | ||
| 8. | scu-frg LDLo:300 mg/kg | QJPPAL Quarterly Journal of Pharmacy and Pharmacology. 9 (1936),37. |
Safety Profile
Poison by intravenous and subcutaneous routes. Human systemic effects by intramuscular route: sleep disturbance, tremors, nausea. When heated to decomposition it emits toxic fumes of NOx.Safety information of Banisterine monohydrate (CAS NO.442-51-3):
Hazard Codes 
Xn
Risk Statements
25 Toxic if swallowed
36 Irritating to the eyes
20/21/22 Harmful by inhalation, in contact with skin and if swallowed
Safety Statements
22 Do not breathe dust
24/25 Avoid contact with skin and eyes
36/37 Wear suitable protective clothing and gloves
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR 1544
WGK Germany 3
RTECS UV0175000
HazardClass 6.1
PackingGroup III
Specification
Harmine is a fluorescent harmala alkaloid belonging to the beta-carboline family of compounds. It occurs in a number of different plants, most notably the Middle Eastern plant harmal or Syrian rue (Peganum harmala) and the South American vine Banisteriopsis caapi ('yage', 'ayahuasca'). Harmine is a reversible monoamine oxidase inhibitor (MAO inhibitor or MAOI) and CNS stimulant. It inhibits MAO-A but has no effect on MAO-B.