Tryptophol

Chemical properties

3-(2-Hydroxyethyl)indole [526-55-6], tryptophol, C10H11NO, Mr 161.20, mp 59 ℃, bp 174 ℃, (2 kPa) forms colorless prisms or flakes that are readily soluble in methanol, ethanol, diethyl ether, chloroform, and acetone, soluble in benzene, and slightly soluble in water. It is produced by reacting methyl-1H-indole-3-acetate with lithium aluminum hydride, or through reduction of methyl-1H-indole-3-glyoxylate with sodium borohydride. The antihypertensive Indoramin is produced from tryptophol.

The Uses of Tryptophol

Tryptophol is a metabolite formed in the liver after disulfiram treatment that induces sleep in humans. It is also a secondary product of alcoholic fermentation.

The Uses of Tryptophol

Reactant for preparation of:

• Inhibitors of the C-terminal domain of RNA polymerase II and their antitumor activities
• Anti-HIV-1 agents
• Inhibitors of Protein-Protein Interactions
• Partial agonists of the serotonin 5-HT1A receptor
• Growth hormone secretagogues
• Vascular endothelial growth factor (VEGF) inhibitors
• A2B adenosine receptor ligands
• Potential detoxification inhibitors of the crucifer phytoalexin brassinin
• Inhibitors of interleukine 6
• Dual binding site acetylcholinesterase inhibitors

What are the applications of Application

3-(2-Hydroxyethyl)indole is an indole for the production of compounds used in biological research

Definition

ChEBI: An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.

Synthesis Reference(s)

Canadian Journal of Chemistry, 42, p. 485, 1964 DOI: 10.1139/v64-070

Purification Methods

Crystallise it from diethyl ether/pet ether, *C6H6, *C6H6/pet ether. The picrate has m 100-101o (from *C6H6). [Beilstein 21 I 218, 21 II 49, 21 III/IV 788, 21/3 V 61.]