26585-14-8

Basic information

• Product Name: 1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole
• Synonyms: 1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole;Crenatine;1-Ethyl-4-methoxy-beta-carboline;Crenatin
• CAS NO: 26585-14-8
• Molecular Formula: C₁₄H₁₄N₂O
• Molecular Weight: 226.27
• Product Categories: Alkaloids
• Mol File: 26585-14-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 168 °C
• Boiling Point: 427.2 °C at 760 mmHg
• Flash Point: 141.4 °C
• Appearance: /
• Density: 1.216 g/cm³
• Vapor Pressure: 4.15E-07mmHg at 25°C
• Refractive Index: 1.684
• PKA: 15.53±0.40(Predicted)
• CAS DataBase Reference: 1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole(26585-14-8)
• EPA Substance Registry System: 1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole(26585-14-8)

Safety Data

• Hazardous Substances Data: 26585-14-8(Hazardous Substances Data)

Usage

General Description

1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole, also known as norharmane, is a chemical compound belonging to the family of indole alkaloids. It is a derivative of the indole molecule, and is characterized by the presence of an ethyl group and a methoxy group in its structure. Norharmane is known for its occurrence in tobacco smoke, as well as in cooked and charred foods. It has been studied for its potential mutagenic and carcinogenic properties, and has been found to be present in higher levels in the urine of smokers. Additionally, norharmane has been investigated for its potential psychoactive effects, with some research suggesting its involvement in the modulation of neurotransmitter systems in the brain.

InChI:InChI=1/C14H14N2O/c1-3-10-14-13(12(17-2)8-15-10)9-6-4-5-7-11(9)16-14/h4-8,16H,3H2,1-2H3

Upstream product

• 6678-86-0 1‐ethyl‐1,2,3,4‐tetrahydro‐β‐carboline 
• 75314-80-6 2-Benzoyl-1-ethyl-1,2,3,9-tetrahydro-β-carbolin-4-one 
• 83478-56-2 1-ethyl-2-(trichloroacetyl)-4-oxo-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 61-54-1 tryptamine 
• 112402-20-7 ethyl N-<1-(1-benzyl-1H-indol-2-yl)propyl>-N-formylaminoacetate 
• 112402-21-8 9-benzyl-1-ethyl-2-formyl-4-oxo-1,2,3,4-tetrahydro-β-carboline 
• 138188-55-3 ethyl 2-methyl-3-oxo-3-(1-benzyl-1H-indol-2-yl)propionate 
• 138188-62-2 9-benzyl-1-ethyl-4-hydroxy-β-carboline 
• 138188-61-1 9-benzyl-1-ethyl-4-oxo-1,2,3,4-tetrahydro-β-carboline 
• 112402-19-4 N-<1-(1-benzyl-1H-indol-2-yl)propyl>formamide 
• 138188-56-4 1-(1-benzyl-1H-indol-2-yl)-1-propanone oxime 
• 112402-18-3 1-(1-benzyl-1H-indol-2-yl)-1-propanone 
• 26585-13-7 1-vinyl-4-dimethoxy-β-carboline 
• 112402-22-9 9-benzyl-1-ethyl-4-methoxy-β-carboline 

Relevant articles and documents

Dichlorodicyanoquinone Oxidations in the Indole Area. Synthesis of Crenatine

The influence of temperature on the reaction of dichlorodicyanoquinone (DDQ) with 1,2,3,4-tetrahydro-β-carbolines has been explored.The DDQ oxidation of amide 2a, when performed at room temperature, gave 3a (3-acylindole)/4 (2-acylindole) in a ratio of ca. 1:1, while this was increased to 2:1 at 0 deg C and to ca. 5:1 at -78 deg C.This method for preparation of 4-oxo-β-carbolines has been employed for synthesis of the β-carboline alkaloid crenatine (11).In addition, treatment of the 4-oxotetrahydro-β-carboline (3b) with hydrazine gave 1-ethyl-4-amino-β-carboline (12) which should provide access to a series of 4-substituted β-carbolines.

DDQ Oxidations in the Indole Area. Synthesis of 4-Alkoxy-β-carbolines Including the Natural Products Crenatine and 1-Methoxycanthin-6-one

The seven-step synthesis of the cytotoxic, antileukemic alkaloid 1-methoxycanthin-6-one (2b) is described.The pivotal steps are represented by the oxidation (DDQ, aqueous THF, room temperature) of 1-(methoxycarbonyl)-1,2,3,4-tetrahydro-β-carboline (10) to provide the 4-oxo-substituted derivative 14 in 78percent yield, and conversion of the 4-oxo analogue 7 into 4-methoxy-1-alkyl-β-carboline (23) via a methoxylation-oxidation process .This four-step, one-pot reaction has been shown to be general; 4-oxo-1,2,3,4-tetrahydro-β-carboline (18) was converted into the corresponding 4-methoxy-, 4-ethoxy-, 4-(allyloxy)-, and 4-(benzyloxy)-β-carbolines (19a-d, respectively) on heating in the appropriate alcohol in the presence of pTSA and a trialkyl orthoformate (Table II).The proposed mechanism for this intriguing transformation is outlined in Scheme IV.Execution of this process has also resulted in a four-step preparation of crenatine (1a), a 4-methoxy-1-ethyl-β-carboline alkaloid.Finally, steric and electronic parameters have also been successfully manipulated to direct the DDQ oxidation of 1,2,3,4-tetrahydro-β-carbolines to position 1, regiospecifically.The conversion of tetrahydro-β-carboline 25 into 2-acylindole 38 and benzamide 26 into 1-oxotetrahydro-β-carboline 27 (Table I), respectively, is in agreement with the proposed mechanism for this process.

The Alkaloids of Picrasma javanica

Extraction of Picrasma javanica Bl. (Simarubaceae) has yielded two new β-carboline alkaloids, 1-ethenyl-4-methoxy-9H-pyrido-indol-5-ol (5-hydroxydehydrocrenatine) (4) and 1-ethyl-4-methoxy-9H-pyridoindol-5-ol (5-hydroxycrenatine) (5), the st