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

Uses

Used in Toxicological Research:
1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole is used as a subject of study in toxicological research for its potential mutagenic and carcinogenic properties. The presence of norharmane in tobacco smoke and its higher levels in the urine of smokers make it a significant compound to investigate in the context of smoking-related health issues.
Used in Neuropharmacological Research:
Norharmane is used as a research compound in neuropharmacology to explore its psychoactive effects and its potential role in modulating neurotransmitter systems in the brain. This application is crucial for understanding the impact of such compounds on cognitive functions and mental health.
Used in Food Industry Analysis:
1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole is used as a marker compound in the analysis of cooked and charred foods, helping to assess the extent of cooking and potentially harmful compounds formed during the cooking process.
Used in Environmental Health Studies:
Norharmane is utilized as an indicator in environmental health studies, particularly in assessing exposure to secondhand smoke and the environmental impact of tobacco smoke constituents.

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

• 61-54-1 tryptamine 
• 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 
• 83478-60-8 1-ethyl-4-oxo-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 83478-56-2 1-ethyl-2-(trichloroacetyl)-4-oxo-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 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 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 83478-61-9 1-ethyl-4-hydroxy-9H-pyrido<3,4-b>indole 
• 83478-55-1 1-ethyl-2-(trichloroacetyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 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 

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.

Synthetic studies of indoles and related compounds. XXVII. A new synthesis of crenatine from ethyl indole-2-carboxylate

Crenatine (1a), which is a member of a new class of β-carboline alkaloids having an oxygen functionality at the 4-position, was synthesized starting from ethyl 1-benzylindole-2-carboxylate (12a) via cyclization of an elaborated C2-substituent to the 3-position of the indole nucleus and aluminum chloride-catalyzed debenzylation of the protected indolic nitrogen. 1-Ethyl-4-hydroxy-9-methyl-β-carboline (26b), a positional isomer of crenatine with regard to the methyl group, was also synthesized through the same methodology.

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.

A NEW ROUTE TO 4-OXYGENATED β-CARBOLINES: THE TOTAL SYNTHESIS OF CRENATINE

Crenatine, a new type of β-carboline alkaloid having an oxygen function at its C4-position, was synthesized using ethyl 1-benzylindole-2-carboxylate as a starting material via cyclization of C2-substituent to C3-position of indole nucleus and AlCl3-catalyzed debenzylation for N-protected indoles.

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