| Identification | More | [Name]
1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE | [CAS]
16502-01-5 | [Synonyms]
1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE
1,2,3,4-TETRAHYDRO-B-CARBOLINE
1,2,3,4-TETRAHYDRO-BETA-CARBOLINE
2,3,4,9-TETRAHYDRO-1H-PYRIDO[3,4-B]INDOLE
AKOS JY2083257
NORELEAGNINE
TETRAHYDRO-BETA-CARBOLINE
TETRAHYDRONORHARMAN
TETRAHYDRONORHARMANE
THBC
TRYPTOLINE
1,2,3,4-Tetrahydro-β-carboline
1H-Pyrido[3,4-b]indole,2,3,4,9-tetrahydro-
2,3,4,9-Tetrahydro-1H-β-carboline
Norharman,1,2,3,4-tetrahydro-
Tetrahydro-β-carboline
2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE
NORELEAGNINE 98%
1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole, Noreleagnine, Tetrahydronorharman, THBC, Tryptoline
1,2,3,4-Tetrahydro-β-carboline, 2,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indole, Tetrahydronorharmane, Tryptoline | [Molecular Formula]
C11H12N2 | [MDL Number]
MFCD00004954 | [Molecular Weight]
172.23 | [MOL File]
16502-01-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Tan Solid | [Melting point ]
206-208 °C(lit.) | [Boiling point ]
351.6±32.0 °C(Predicted) | [density ]
1.189±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
10mg/mL in 1N Ammonium Hydroxide in Methanol, DMSO | [form ]
Powder or Crystals | [pka]
17.78±0.20(Predicted) | [color ]
White to slightly yellow | [Usage]
Used in the study of neurodegenerative diseases | [InChI]
InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 | [InChIKey]
CFTOTSJVQRFXOF-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC=C2)C2CCNCC1=2 | [LogP]
1.816 (est) | [CAS DataBase Reference]
16502-01-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Tan Solid | [Uses]
A mitotic kinesin inhibitor as novel anti-cancer agent. | [Uses]
1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole is used in the study of neurodegenerative diseases
| [Uses]
A mitotic kinesin inhibitor as novel anti-cancer agent. Used in the study of neurodegenerative diseases. | [Application]
1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole was employed in alkaloid synthesis and in studies on neurodegenerative diseases.
Reactant for synthesis of the indolyl-β-carboline alkaloid eudistomin U via IBX mediated room temperature oxidative aromatization
Reactant for preparation of neuroprotective HDAC6 inhibitors
Reactant for preparation of aminofuranopyrimidines as EGFR and Aurora A kinase inhibitors
Reactant for preparation of inhibitors of CDK4
Reactant for preparation of tetrahydrocarboline derivatives of as human 5-HT5A receptor ligands
Reactant for preparation of 5-(diaminomethyl)-2,4-aminopyrimidines as dihydrofolate reductase inhibitors and antibacterial agents | [Definition]
ChEBI: 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole is a member of beta-carbolines. | [General Description]
Ozonolysis of the enamine bond of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole derivatives was studied. | [Synthesis]
1.5 g of tryptamine was dissolved in a mixed acetic acid/methanol solvent (AcOH/MeOH = 10:1, v/v) and 345 mg of paraformaldehyde was slowly added. The reaction mixture was stirred at 80 °C for 30 min. After completion of the reaction, the progress of the reaction was monitored by TLC. The reaction system was slowly poured into dilute aqueous ammonia solution (NH4OH/H2O = 1:1, v/v, 80 ml) and the pH was adjusted to 10. The organic phases were combined by extracting three times with a solvent mixture of dichloromethane/methanol (CH2Cl2/MeOH = 10:1, v/v). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with dichloromethane/methanol (CH2Cl2/MeOH = 10:1, v/v) as eluent to give 1.6 g of Intermediate A in 98% yield. The product was a light yellow solid, stable at room temperature. | [in vivo]
Tetrahydro-β-carboline (20 μg; i.c.v.) increases the serotonin levels in the same part of the brain in rats[1]. | Animal Model: | 180-200g female Sprague-Dawley rats[1] | | Dosage: | 20 μg | | Administration: | Intraventricular injection | | Result: | Increased of serotonin levels in the same part of the brain whereas the monoamine oxidase activity was not altered. |
| [IC 50]
serotonin: 6.1 μM (Ki) | [References]
[1] CHRISTIAN O ALBERTO Michiru H Robert B Trask. Dopamine acts as a partial agonist for α2A adrenoceptor in melanin-concentrating hormone neurons.[J]. Journal of Neuroscience, 2011, 31 29: 10671-10676. DOI:10.1523/JNEUROSCI.6245-10.2011.
[2] IAIN M. MCDONALD. 2,7-Dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1,4]diazonine as a New Template for the Design of CCK2 Receptor Antagonists[J]. Journal of Medicinal Chemistry, 2000, 43 19: 3518-3529. DOI:10.1021/jm000960w.
[3] Rommelspacher, H., Bade, P., Coper, H., et al. Inhibition of the reuptake of serotonin by tryptoline. Naunyn Schmiedebergs Arch. Pharmacol. 292(1), 93-95 (1976).
[4] Pannier, L., and Rommelspacher, H. Actions of tetrahydronorharmane (tetrahydro-β-carboline) on 5-hydroxytryptamine and dopamine mediated mechanisms. Neuropharmacology 20(1), 1-8 (1981).
[5] Rommelspacher, H., Kauffmann, H., Cohnitz, C.H., et al. Pharmacological properties of tetrahydronorharmane (tryptoline). Naunyn Schmiedebergs Arch. Pharmacol. 298(2), 83-91 (1977). |
| Spectrum Detail | Back Directory | [Spectrum Detail]
1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE(16502-01-5)1HNMR
1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE(16502-01-5)Raman
1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE(16502-01-5)FT-IR
1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE(16502-01-5)IR
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