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Basic Information
CAS No.: 244-63-3
Name: 9H-Pyrido[3,4-b]indole
Molecular Structure:
Molecular Structure of 244-63-3 (9H-Pyrido[3,4-b]indole)
Formula: C11H8 N2
Molecular Weight: 168.198
Synonyms: 2,9-Diazafluorene;2-Azacarbazole; Carbazoline; NSC 84417; Norharman; Norharmane; b-Carboline
EINECS: 205-959-0
Density: 1.301 g/cm3
Melting Point: 199-201 °C
Boiling Point: 391.3 °C at 760 mmHg
Flash Point: 182.1 °C
Solubility: 2693g/L(17 oC)
Appearance: light yellow crystalline
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: Poison by intravenous route. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
PSA: 28.68000
LogP: 2.71610
Synthetic route
5667-11-8

2-methyl-β-carboline-2-ium iodide

244-63-3

betacarboline

Conditions
ConditionsYield
With pyridine hydrochloride for 10h; Heating;98%
16502-01-5

tetrahydrobetacarboline

244-63-3

betacarboline

Conditions
ConditionsYield
With palladium 10% on activated carbon In para-xylene at 145℃; for 72h;95%
With dihydrogen peroxide; iodine In water; dimethyl sulfoxide at 5℃;88%
Stage #1: tetrahydrobetacarboline In tetrahydrofuran at -78℃; for 2h;
Stage #2: With oxygen In tetrahydrofuran at 20℃; Reagent/catalyst;
83%
58911-02-7

Tryptoline hydrochloride

244-63-3

betacarboline

Conditions
ConditionsYield
With 5 mol% Pd/C; lithium carbonate In ethanol at 150℃; for 1h; Sealed tube; Microwave irradiation;95%
With lithium carbonate; silver carbonate In N,N-dimethyl-formamide for 19h; Reflux;53%
25797-02-8

6,7,8,9-tetrahydro-5H-pyrido[3,4-b]indole

244-63-3

betacarboline

Conditions
ConditionsYield
With palladium on activated carbon In diphenylether at 210℃; for 0.66h; Inert atmosphere;94%

4-[2-(2,2-Dimethyl-propionylamino)-phenyl]-3-fluoro-1-methyl-pyridinium; iodide

244-63-3

betacarboline

Conditions
ConditionsYield
With pyridine hydrochloride for 10h; Heating;92%
557086-56-3

4a-(4-methyl-3,5-dioxo-[1,2,4]triazolidin-1-yl)-3,4,4a,9-tetrahydro-β-carboline-2-carboxylic acid methyl ester

244-63-3

betacarboline

Conditions
ConditionsYield
at 250℃;90%
146141-07-3

2,2-dimethyl-N-(2-(3-fluoro-4-pyridyl)phenyl)propanamide

244-63-3

betacarboline

Conditions
ConditionsYield
With pyridine hydrochloride for 0.25h;86%

2‐tosyl‐2,3,4,9‐tetrahydro‐1H‐pyrido[3,4‐b]indole

244-63-3

betacarboline

Conditions
ConditionsYield
Stage #1: 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℃;
86%
42438-90-4

3-carboxy-1,2,3,4-tetrahydro-2-carboline

244-63-3

betacarboline

Conditions
ConditionsYield
With iron(III) chloride In N,N-dimethyl-formamide at 130℃; for 1h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Green chemistry;83%
With copper dichloride In N,N-dimethyl-formamide at 130℃; for 1h; Reagent/catalyst;81%
With N-chloro-succinimide; triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;80%
6052-68-2

1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

244-63-3

betacarboline

Conditions
ConditionsYield
With tetrasodium cobalt(II) 4,4',4'',4'''-tetrasulphophthalocyanine In ethanol; water; ethyl acetate at 20℃; for 24h; Irradiation; Green chemistry;82%
With selenium(IV) oxide; acetic acid for 24h; Heating;62%
With potassium dichromate; acetic acid In water for 1h; Heating;55.3%
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Chemistry

IUPAC Name: 9H-Pyrido[3,4-b]indole
Synonyms of Norharman (CAS NO.244-63-3) : .beta.-Carboline ; 9H-beta-Carbolin ; 9H-beta-Carboline ; 9H-pyrido[3,4-b]indole ; b-Carboline
InChI:InChI=1/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
Product Categories: Miscellaneous Natural Products;Heterocycles;Mutagenesis Research Chemicals
CAS NO:244-63-3
Molecular Formula:C11H8N2                                  
Molecular Weight :168.1946                                         
Molecular Structure :
EINECS: 205-959-0 
Index of Refraction: 1.784   
Surface Tension: 66.2 dyne/cm 
Density: 1.301 g/cm3 
Flash Point: 182.1 °C 
Enthalpy of Vaporization: 61.58 kJ/mol 
Boiling Point: 391.3 °C at 760 mmHg 
Vapour Pressure: 5.62E-06 mmHg at 25°C 
Melting Point: 199-201 °C 
Storage temp:  2-8°C
Appearance: Norharman (CAS NO.244-63-3) is off-white solid .

Uses

 Norharman (CAS NO.244-63-3) has cytotoxic effects.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02316,

Safety Profile

Poison by intravenous route. Experimental reproductive effects. Human mutation data reported. When Norharman (CAS NO.244-63-3) is heated to decomposition, it emits toxic fumes of NOx.

Hazard Codes HarmfulXn
Risk Statements 22
R22:Harmful if swallowed.
Safety Statements 36/37/39-26-22
S22:Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany 3
RTECS UU9350000