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| CAS No.: | 486-84-0 |
|---|---|
| Name: | HARMANE |
| Article Data: | 91 |
| Molecular Structure: | |
|
|
|
| Formula: | C12H10 N2 |
| Molecular Weight: | 182.225 |
| Synonyms: | 2,9-Pyridindole,1-methyl- (3CI); 1-Methyl-9H-pyrido[3,4-b]indole; 1-Methyl-b-carboline; Aribin; Aribine;Harman; Harmane; Indoter; Locuturin; Locuturine; NSC 54439; Zygofabagine |
| Density: | 1.252g/cm3 |
| Melting Point: |
235-238 °C(lit.) |
| Boiling Point: | 386.9°Cat760mmHg |
| Flash Point: | 176.2°C |
| Solubility: | 1523g/L(20 oC) |
| Appearance: | Off-White Solid |
| Hazard Symbols: |
|
| Risk Codes: | 20/21 |
| Safety: | Poison by intraperitoneal route. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx. |
| PSA: | 28.68000 |
| LogP: | 3.02450 |
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| Conditions | Yield |
|---|---|
| With acid | 88.7% |
| Stage #1: tryptamine; acetaldehyde With piperidine; methanesulfonic acid at 100℃; for 4h; Sealed tube; Stage #2: With triethylamine In water Stage #3: With palladium on activated charcoal at 180℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere; | 80.2% |
| Yield given; |
| Conditions | Yield |
|---|---|
| With C21H21ClIrNO2 In tetrahydrofuran; 2,2,2-trifluoroethanol for 20h; Inert atmosphere; | 93% |
| With [bis(acetoxy)iodo]benzene In N,N-dimethyl-formamide at 20℃; for 1h; | 84% |
| With 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(ll) bromide In dimethyl sulfoxide at 25℃; for 24h; Green chemistry; | 81% |
- 5470-37-1, 40678-46-4, 42438-72-2, 96149-76-7, 98718-62-8, 114497-71-1, 143396-05-8
1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid
- 486-84-0
harmane
| Conditions | Yield |
|---|---|
| With tetrasodium cobalt(II) 4,4',4'',4'''-tetrasulphophthalocyanine In water; ethyl acetate at 20℃; for 24h; Irradiation; Green chemistry; | 87% |
| With ammonium persulfate; silver nitrate In water; acetonitrile at 80℃; | 56% |
| Multi-step reaction with 2 steps 1: acetic acid; water / 0.33 h / 100 °C 2: sodium hydroxide; sodium hydrogensulfite View Scheme | |
| With manganese(IV) oxide; sulfuric acid |
- 191279-37-5
(3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
- 486-84-0
harmane
| Conditions | Yield |
|---|---|
| With copper dichloride In N,N-dimethyl-formamide at 130℃; for 1h; | 84% |
| With N-chloro-succinimide; triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; | 82% |
| With iron(III) chloride In N,N-dimethyl-formamide at 130℃; for 1h; Catalytic behavior; Green chemistry; | 82% |
- 486-84-0
harmane
| Conditions | Yield |
|---|---|
| With 2 mol-% Pd/C; lithium carbonate In ethanol at 150℃; for 0.166667h; Sealed tube; Microwave irradiation; | 93% |
| With lithium carbonate; silver carbonate In N,N-dimethyl-formamide for 1h; Reflux; | 34% |
| Conditions | Yield |
|---|---|
| With potassium permanganate In acetone at 20℃; | 92% |
| With C21H21ClIrNO2 In tetrahydrofuran; 2,2,2-trifluoroethanol for 20h; Inert atmosphere; | 81% |
| With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 125℃; for 10h; | 76% |
- 486-84-0
harmane
| Conditions | Yield |
|---|---|
| With ammonium acetate In acetic acid; N,N-dimethyl-formamide at 120℃; for 7h; | 90 mg |
- 486-84-0
harmane
| Conditions | Yield |
|---|---|
| Stage #1: C13H16N2O2 With manganese(IV) oxide In water at 100℃; for 0.0833333h; Stage #2: With sulfuric acid In water at 100℃; for 1h; |
| Conditions | Yield |
|---|---|
| Stage #1: N-Acetyltryptamine With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In chlorobenzene at 20 - 130℃; Stage #2: With manganese(IV) oxide In chlorobenzene at 130℃; for 4h; | 82% |
| Stage #1: N-Acetyltryptamine With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In chlorobenzene Stage #2: With manganese(IV) oxide In chlorobenzene | 80% |
| With trichlorophosphate In toluene; acetonitrile for 3h; Reflux; |
| Conditions | Yield |
|---|---|
| With oxygen; sodium hydroxide In water; dimethyl sulfoxide at 125℃; for 5h; | 82% |
| Stage #1: 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℃; | 74% |
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Chemistry
IUPAC Name: 1-Methyl-9H-pyrido[3,4-b]indole
The MF of 1-Methyl-9H-pyrido[3,4-b]indole (CAS NO.486-84-0) is C12H10N2.
The MW of 1-Methyl-9H-pyrido[3,4-b]indole (CAS NO.486-84-0) is 182.22.
Synonyms of 1-Methyl-9H-pyrido[3,4-b]indole (CAS NO.486-84-0): 1-Methyl-.beta.-carboline ; 1-Methyl-9H-pyrid[3,4-b]indole ; 2-Methyl-b-carboline ; 9H-Pyrido[3,4-b]indole, 1-methyl-
Product Categories: Heterocyclic Compounds;Mutagenesis Research Chemicals
Apperance: Off-White Solid
Index of Refraction: 1.75
EINECS: 207-642-2
Density: 1.252 g/ml
Flash Point: 176.2 °C
Boiling Point: 386.9 °C
Melting Point: 235-238 °C
Merck: 13,4630
Uses
1-Methyl-9H-pyrido[3,4-b]indole (CAS NO.486-84-0) is harman alkaloid like harmane, harmine, harmalol, harmaline obtained from Banisteriopsis caapi L which showed cytotoxicity, antimicrobial activity against Staphylococcus aureus, Escherichia coli, Proteus vulgaris and Candida albicans.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 50mg/kg (50mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 164, 1964. |
| rabbit | LD50 | subcutaneous | 200mg/kg (200mg/kg) | Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963. |
Safety Profile
Poison by intraperitoneal route. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.Safety information of 1-Methyl-9H-pyrido[3,4-b]indole (CAS NO.486-84-0):
Hazard Codes 
Xn,Xi
Risk Statements
20/21 Harmful by inhalation and in contact with skin
36/37/38 Irritating to eyes, respiratory system and skin
Safety Statements
22 Do not breathe dust
24/25 Avoid contact with skin and eyes
36 Wear suitable protective clothing
RIDADR 1544
WGK Germany 3
RTECS UV0280000
HazardClass 6.1(b)
PackingGroup III