17337-22-3

Basic information

• Product Name: 1-(Hydroxymethyl)-β-carboline
• Synonyms: 1-(Hydroxymethyl)-β-carboline;(9H-pyrido[3,4-b]indol-1-yl)methanol;9H-PYRIDO[3,4-B]INDOLE-1-METHANOL
• CAS NO: 17337-22-3
• Molecular Formula: C12H10N2O
• Molecular Weight: 198.2206
• Mol File: 17337-22-3.mol

Chemical Properties

• Boiling Point: 466°C at 760 mmHg
• Flash Point: 235.6°C
• Appearance: /
• Density: 1.385g/cm³
• Vapor Pressure: 1.74E-09mmHg at 25°C
• Refractive Index: 1.795
• CAS DataBase Reference: 1-(Hydroxymethyl)-β-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Hydroxymethyl)-β-carboline(17337-22-3)
• EPA Substance Registry System: 1-(Hydroxymethyl)-β-carboline(17337-22-3)

Safety Data

• Hazardous Substances Data: 17337-22-3(Hazardous Substances Data)

Usage

Chemical class

β-carbolines

Structure

Contains a hydroxymethyl group attached to the β-carboline backbone

Natural occurrence

Commonly found in various natural products

Biological activities

Linked to a range of biological activities

Pharmacological properties

Involvement in neurotransmission, neurotoxicity, and potential drug candidates for neurological disorders

Specific receptor interaction

Identified as a potential trace amine-associated receptor (TAAR) ligand

Implications

Modulating neurotransmitter systems in the brain

Potential therapeutic applications

Targeting the central nervous system

Research focus

Further investigation into pharmacological properties for potential medical applications

InChI:InChI=1/C12H10N2O/c15-7-11-12-9(5-6-13-11)8-3-1-2-4-10(8)14-12/h1-6,14-15H,7H2

Upstream product

• 6052-68-2 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 
• 3464-66-2 methyl 9H-pyrido[3,4-b]indole-1-carboxylate 
• 73198-02-4 optically inactive 1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid 
• 26052-96-0 9H-pyrido<3,4-b>indole-1-carboxylic acid 
• 18110-86-6 4-methoxy-5-hydroxyl-canthin-6-one 
• 18110-87-7 4,5-dimethoxy-canthin-6-one 
• 59132-30-8 1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylic acid 
• 73-22-3 L-tryptophan 
• 67-56-1 methanol 
• 244-63-3 betacarboline 
• 102991-38-8 1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid 
• 61-54-1 tryptamine 
• 127661-45-4 methyl 2,3,4,9-tetrahydro-1H-pyrido [3,4-b]indole-1-carboxylate 
• 1205667-14-6 1-(dimethoxymethyl)-9H-pyrido[3,4-b]indole 

Relevant articles and documents

Electrochemistry of Natural Products. 7. Oxidative Decarboxylation of Some Tetrahydro-β-carbolinecarboxylic Acids

A series of 1,2,3,4-tetrahydro-β-carboline-1- and -3-carboxylic acids containing various substituents in positions 1, 2, and 3 were oxidized electrochemically.In general, the acids were decarboxylated, and unsaturation was introduced into the C ring.The oxidation appears to take place through the indole ring nitrogen, and possible mechanisms of the reactions are presented.Parallels between the observed reactions and early steps in indole alkaloid biosynthesis are discussed.The oxidative dimerization of tetrahydrocarbazole is reported.

A facile synthesis of 1-substituted βcarboline derivatives via minisci-reaction

A mild and efficient one-pot reaction for the synthesis of 1-substituted βcarboline derivatives via the Minisci reaction has been developed with good yields and selectivity. In addition, the mechanism of the 1-substituted βcarboline derivatives by means of the nucleophilic radical is described.

Further investigation of harmicines as novel antiplasmodial agents: Synthesis, structure-activity relationship and insight into the mechanism of action

The rise of the resistance of the malaria parasite to the currently approved therapy urges the discovery and development of new efficient agents. Previously we have demonstrated that harmicines, hybrid compounds composed from β-carboline alkaloid harmine

First total synthesis of the β-carboline alkaloids trigonostemine A, trigonostemine B and a new synthesis of pityriacitrin and hyrtiosulawesine

The total synthesis of four natural products, trigonostemine A, trigonostemine B, pityriacitrin, and hyrtiosulawesine was accomplished. The key intermediates, variously substituted 1-formyl-β-carbolines, were prepared in five steps via a novel synthetic approach using readily available starting materials. These formyl derivatives were then further transformed, providing a general route for the synthesis of the four title alkaloids. The method reported herein represents the first total synthesis of the two trigonostemines and a new pathway to pityriacitrin and hyrtiosulawesine.

Studies on the Constituents of Picrasma quassioides BENNET. III. The Alkaloidal Constituents

A new β-carboline alkaloid, named picrasidine E(I), was isolated from the wood of Picrasma quassioides BENNET (Simaroubaceae) together with seven known alkaloids, 1-methoxycarbonyl-β-carboline (II), 1-ethoxycarbonyl-β-carboline (III), 1-formyl-β-carboline (IV), 1-hydroxymethyl-β-carboline (V), β-carboline-1-propionic acid (VI), 4,5-dimethoxy-canthin-6-one (VII), and 5-hydroxy-4-methoxycanthin-6-one (VIII).These structures were elucidated on the basis of spectroscopic and chemical evidence.Keywords - Picrasma quassioides; Simaroubaceae; wood; picrasidine E; β-carboline type alkaloid; canthin-6-one type alkaloid.

9H-Pyrido[3,4-b]indole derivatives

1-Substituted-9H-pyrido[3,4-b]indole derivatives, which are further optionally substituted in the 3- or 4-position, are inhibitors of xanthine-oxidase. A representative embodiment is 1-formyl-4-hydroxy-9H-pyrido[3,4-b]indole which can be prepared through