1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE
- Product Name
- 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE
- CAS No.
- 16502-01-5
- Chemical Name
- 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE
- Synonyms
- THBC;TRYPTOLINE;4-B]INDOLE;NORELEAGNINE;Noreleaginine;AKOS JY2083257;NORELEAGNINE 98%;TETRAHYDRONORHARMAN;TETRAHYDRONORHARMANE;Tetrahydro-β-carboline
- CBNumber
- CB7358663
- Molecular Formula
- C11H12N2
- Formula Weight
- 172.23
- MOL File
- 16502-01-5.mol
1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE Property
- 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
- pka
- 17.78±0.20(Predicted)
- form
- Powder or Crystals
- color
- White to slightly yellow
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 300764
- Product name
- 1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole
- Purity
- 98%
- Packaging
- 1g
- Price
- $39.8
- Updated
- 2025/07/31
- Product number
- 300764
- Product name
- 1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole
- Purity
- 98%
- Packaging
- 5g
- Price
- $119
- Updated
- 2025/07/31
- Product number
- T293250
- Product name
- 1,2,3,4-Tetrahydro-β-carboline
- Packaging
- 1g
- Price
- $45
- Updated
- 2021/12/16
- Product number
- T293250
- Product name
- 1,2,3,4-Tetrahydro-β-carboline
- Packaging
- 10g
- Price
- $230
- Updated
- 2021/12/16
- Product number
- T2970-44
- Product name
- 1,2,3,4-Tetrahydro-b-carboline
- Packaging
- 1g
- Price
- $312
- Updated
- 2021/12/16
1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE Chemical Properties,Usage,Production
Chemical Properties
Tan Solid
Uses
1,2,3,4-Tetrahydro-β-carboline is a mitotic kinesin inhibitor as novel anti-cancer agent. It is 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
50-00-0
61-54-1
16502-01-5
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).
1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE manufacturers
- Product
- 1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole 98% 16502-01-5
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-06-27
- Product
- 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE 16502-01-5
- Price
- US $1.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 200
- Release date
- 2018-12-23