9H-PYRIDO[3,4-B]INDOLE

Iupac Name：9H-pyrido[3,4-b]indole

Molecular Weight：304.38736

Modify Date.: 2022-11-29 08:38

Introduction:

Norharmane (Norharman), isolated from coffee, is a potent and selective monoamine oxidase A (MAO-A) inhibitor with a Ki of 3.34 μM[1].

Solid

Beta-carboline is the parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring. It has a role as a marine metabolite and a fungal metabolite. It is a member of beta-carbolines and a mancude organic heterotricyclic parent.

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1. Names and Identifiers

: 1.1 Name; 9H-PYRIDO[3,4-B]INDOLE; 1.2 Synonyms; 2-Azacarbazole 9H-Β-Carboline b-carboline betacarboline beta-carboline CARBAZOLINE EINECS 205-959-0 MFCD00004956 Nor Harmane norhaman Norharman Norharmane Pyridoindole Β-carboline; View all

1.3 CAS No.: 244-63-3

1.4 CID: 64961

1.5 EINECS(EC#): 205-959-0

1.6 Molecular Formula: C11H8N2 (isomer)

1.7 Inchi: InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

1.8 InChIkey: AIFRHYZBTHREPW-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C2C(=C1)C3=C(N2)C=NC=C3

1.10 Isomers Smiles: C1=CC=C2C(=C1)C3=C(N2)C=NC=C3

2. Properties

2.1 Density: 1.301

2.1 Melting point: 199-201 °C

2.1 Boiling point: 391.3 °C at 760 mmHg

2.1 Refractive index: 1.784

2.1 Flash Point: 182.1 °C

2.1 Precise Quality: 168.06900

2.1 PSA: 28.68000

2.1 logP: 2.71610

2.1 Solubility: 2693g/L(17 ºC)

2.2 Appearance: light yellow crystalline

2.3 Chemical Properties: Off-White Solid

2.4 Color/Form: light yellow

2.5 pKa: 15.44±0.30(Predicted)

2.6 Water Solubility: 2693g/L(17 oC)

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.

3.2 Usage: The compund has cytotoxic effects

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R22

4.1 Safety Statements: Poison by intravenous route. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

4.1 Hazard Declaration: H302

4.1 RIDADR: 3261

4.1 Safety Profile: Poison by intravenous route.Experimental reproductive effects. Human mutation datareported. When heated to decomposition it emits toxicfumes of NOx. 9H-PYRIDO[3,4-B]INDOLESupplier

4.2 Caution Statement: P264, P270, P301+P312, P330, P501

4.2 WGK Germany: 3

4.2 RTECS: UU9350000

4.2 Safety

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 NO_x.

Hazard Codes Harmful Xn
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

4.3 Toxicity: dnd-hmn:hla 50 mmol/L MUREAV 89,95,81

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/…if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

1H NMR : 400 MHz in CDCl3

1H NMR : parameter in acetone

1H NMR : parameter in DMSO-d6

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

244-63-3Total: 51 Synthesis Route

61-54-1 223 Suppliers

244-63-3 34 Suppliers

Literatures:
Chemische Berichte, , vol. 63, p. 2102,2106
Yield: null

88-75-5 105 Suppliers

244-63-3 34 Suppliers

Literatures:
Heterocycles, , vol. 48, # 8 p. 1513 - 1518
Yield: null

98-80-6 427 Suppliers

244-63-3 34 Suppliers

Literatures:
Synlett, , # 1 art. no. G33904ST, p. 127 - 133
Yield: null

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8. Precursor and Product

precursor:

343-94-2

4282-49-9

6250-88-0

98-80-6

6052-68-2

16502-01-5

486-84-0

4894-26-2

54-12-6

5667-11-8

591-50-4

88-75-5

1120-87-2

61-54-1

42438-90-4

73-22-3

5570-19-4

372-47-4

84518-77-4

View all

product :

361202-25-7

20127-63-3

752213-27-7

219959-85-0

88704-40-9

2521-07-5

30684-41-4

486-84-0

22946-01-6

9. Other Information

9.0 Collision Cross Section: 132.2 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

9.1 Mesh: Toxic substances from microorganisms, plants or animals that interfere with the functions of the nervous system. Most venoms contain neurotoxic substances. Myotoxins are included in this concept. (See all compounds classified as Neurotoxins.)|Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)

9.2 Chemical Properties: Off-White Solid

9.3 Uses: The compund has cytotoxic effects

9.4 Definition: ChEBI: The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.

9.5 Hazard: Toxic; nervous system effects.

10. Computational chemical data

Molecular Weight: 304.38736g/mol
Molecular Formula: C₁₁H₈N₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 168.068748264
Monoisotopic Mass: 168.068748264
Complexity: 193
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 28.7
Heavy Atom Count: 13
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzAAAAAAAAAAAAAAAAAAAAAWAAAAA8QAAAAAAAAFgB/gAAHAAQAAAADAjBHgQ8wPLJkACgAzRnRACCgCQxEiAI2SA4dJgIYOLAkZGUIAhgkADIyAcQgMAOgAAAAAACAAAAAAAAAAQAAAAAAAAAAA==

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