1-Methyl-9H-pyrido[3,4-b]indole supplier

Name
HARMANE
EINECS
CAS No. 486-84-0
Article Data91
CAS DataBase
Density 1.252g/cm³
Solubility 1523g/L(20 oC)
Melting Point 235-238 °C(lit.)
Formula C12H10 N2
Boiling Point 386.9°Cat760mmHg
Molecular Weight 182.225
Flash Point 176.2°C
Transport Information
Appearance Off-White Solid
Safety Poison by intraperitoneal route. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
Risk Codes 20/21
Molecular Structure
Hazard Symbols
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
PSA 28.68000
LogP 3.02450

Synthetic route

: 61-54-1
tryptamine

: 75-07-0
acetaldehyde

: 486-84-0
harmane

Conditions

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;

: 2506-10-7
eleagnine

: 486-84-0
harmane

Conditions

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

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

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%

: 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole trifluoroacetate

: 486-84-0
harmane

Conditions

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%

: 525-41-7
1-methyl-4,9-dihydro-3H-β-carboline

: 486-84-0
harmane

Conditions

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%

: C14H15NO2

: 486-84-0
harmane

Conditions

Conditions	Yield
With ammonium acetate In acetic acid; N,N-dimethyl-formamide at 120℃; for 7h;	90 mg

: C13H16N2O2

: 486-84-0
harmane

Conditions

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;

: 1016-47-3
N-Acetyltryptamine

: 486-84-0
harmane

Conditions

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;

: 5159-20-6
1-methyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

: 486-84-0
harmane

Conditions

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%

: 31965-09-0
1-methyl-6,7,8,9-tetrahydro-5H-pyrido[3,4-b]indole

: 486-84-0
harmane

Conditions

Conditions	Yield
With palladium on activated carbon In diphenylether at 210℃; for 0.66h; Inert atmosphere;	91%
With palladium on activated charcoal; diphenylether; biphenyl

: 6678-82-6
(+/-)-Calligonine hydrochloride

: 486-84-0
harmane

Conditions

Conditions	Yield
With 5 mol% Pd/C; lithium carbonate In ethanol at 150℃; for 0.1h; Sealed tube; Microwave irradiation;	92%

: 6-bromo-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

: 486-84-0
harmane

Conditions

Conditions	Yield
With 5 mol% Pd/C; lithium carbonate In ethanol at 150℃; for 0.75h; Sealed tube; Microwave irradiation;	75%

: 3-azido-2-methyl-4-phenylpyridine

: 486-84-0
harmane

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 10h; Reflux;	45%

: 75-91-2
tert.-butylhydroperoxide

: 244-63-3
betacarboline

: 486-84-0
harmane

Conditions

Conditions	Yield
With iron(II) sulfate In sulfuric acid; water; acetic acid at 0℃; for 2h;	75%

: 6-chloro-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

: 486-84-0
harmane

Conditions

Conditions	Yield
With 5 mol% Pd/C; lithium carbonate In ethanol at 150℃; for 0.1h; Sealed tube; Microwave irradiation;	60%

: 127-19-5
N,N-dimethyl acetamide

: 82980-12-9
1-(phenylsulfonyl)-3-vinyl-1H-indole

: 486-84-0
harmane

Conditions

Conditions	Yield
Stage #1: 3-ethenyl-1-phenylsulfonyl-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;	46%

: 127-19-5
N,N-dimethyl acetamide

: 110128-40-0
(E)-1-(Phenylsulfonyl)-3-(β-methoxyvinyl)indole

: 486-84-0
harmane

Conditions

Conditions	Yield
Stage #1: (E)-1-(Phenylsulfonyl)-3-(β-methoxyvinyl)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;	53%

: 127-19-5
N,N-dimethyl acetamide

: 211738-25-9
(E)-3-(2-nitrovinyl)-1-(phenylsulfonyl)-1H-indole

: 486-84-0
harmane

Conditions

Conditions	Yield
Stage #1: (E)-3-(2-nitrovinyl)-1-(phenylsulfonyl)-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;	45%

: 73-22-3
L-Tryptophan

: 486-84-0
harmane

Conditions

Conditions	Yield
With sulfuric acid; acetaldehyde Oxydieren der Reaktionsloesung mit Kaliumdichromat;
With acetic anhydride; zinc(II) chloride Oxydieren des entstandenen Oels mit Chromschwefelsaeure;
Multi-step reaction with 2 steps 1: acetic acid / 3 h / Reflux 2: acetic acid; potassium dichromate / water / 0.33 h / 100 °C View Scheme

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

: 486-84-0
harmane

Conditions

Conditions	Yield
With pyridine hydrochloride at 210℃; for 0.25h;	84%

: 61-54-1
tryptamine

: 486-84-0
harmane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / water / 0.5 h / 20 °C 1.2: 7 h / Reflux 2.1: maleic acid; palladium on activated charcoal / water / 8 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / water / 7 h / Reflux 2: maleic acid; palladium on activated charcoal / water / 8 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 0.05 h / 110 °C / Sealed tube; Microwave irradiation 2: lithium carbonate; 2 mol-% Pd/C / ethanol / 0.17 h / 150 °C / Sealed tube; Microwave irradiation View Scheme

: 22329-38-0
harman-3-carboxylic acid

: 486-84-0
harmane

Conditions

Conditions	Yield
With copper In quinoline at 240℃; for 1h;
With sodium hydrogensulfite; sodium hydroxide

: C15H15N3O

A: 486-84-0
harmane

B: C14H16N2O

Conditions

Conditions	Yield
With sodium cyanoborohydride In tetrahydrofuran; methanol at 65℃; Inert atmosphere;	A n/a B 20%

: 75-24-1
trimethylaluminum

: 102337-43-9
1-Chlor-9H-pyrido<3,4-b>indol

: 486-84-0
harmane

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; hexane for 3h; Heating;	66%

: 668987-16-4
methyl 5-acetyl-4-[(β-carbolin-1-yl)methyl]-1,4-dihydropyridine-3-carboxylate

A: 486-84-0
harmane

B: 38940-64-6
5-(1'-hydroxyethyl) nicotinic acid methyl ester

C: 52811-49-1
methyl 4-[(β-carbolin-1-yl)methyl]-5-(1-hydroxyethyl)-1,4-dihydropyridine-3-carboxylate

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 0.25h;

...Expand

: 80360-20-9
1-(phenylsulfonyl)indole-3-carbaldehyde

: 486-84-0
harmane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 63 percent / AcONa; AcOH 2.1: LDA / tetrahydrofuran / 1 h / -78 °C 2.2: tetrahydrofuran / -78 - -10 °C 2.3: 45 percent / NH2OH*HCl; AcONa / 1,2-dichloro-benzene / 8 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: 65 percent / t-BuOK / tetrahydrofuran 2.1: LDA / tetrahydrofuran / 1 h / -78 °C 2.2: tetrahydrofuran / -78 - -10 °C 2.3: 46 percent / NH2OH*HCl; AcONa / 1,2-dichloro-benzene / 8 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: 77 percent / t-BuOK / tetrahydrofuran 2.1: LDA / tetrahydrofuran / 1 h / -78 °C 2.2: tetrahydrofuran / -78 - -10 °C 2.3: 53 percent / NH2OH*HCl; AcONa / 1,2-dichloro-benzene / 8 h / Heating View Scheme

: 75-07-0
acetaldehyde

: 73-22-3
L-Tryptophan

: 486-84-0
harmane

Conditions

Conditions	Yield
With hydrogenchloride; iron(III) chloride In N,N-dimethyl-formamide at 130℃; for 1h; Catalytic behavior; Pictet-Spengler Synthesis; Green chemistry;	78%
Stage #1: acetaldehyde; L-Tryptophan Acidic conditions; Stage #2: With potassium dichromate
With potassium dichromate

: 2506-09-4
Harman-2-oxide

: 486-84-0
harmane

Conditions

Conditions	Yield
With acetic acid; zinc for 2h; Reduction;	87%

1-Methyl-9H-pyrido[3,4-b]indole Chemical Properties

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

1-Methyl-9H-pyrido[3,4-b]indole 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.

1-Methyl-9H-pyrido[3,4-b]indole 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.

1-Methyl-9H-pyrido[3,4-b]indole Safety Profile

Poison by intraperitoneal route. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.Safety information of 1-Methyl-9H-pyrido[3,4-b]indole (CAS NO.486-84-0):
Hazard Codes Harmful 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

Product Name

HARMANE

Synthetic route

1-Methyl-9H-pyrido[3,4-b]indole Chemical Properties

1-Methyl-9H-pyrido[3,4-b]indole Uses

1-Methyl-9H-pyrido[3,4-b]indole Toxicity Data With Reference

1-Methyl-9H-pyrido[3,4-b]indole Safety Profile

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