INDOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H7N
Molecular Weight	117.1479
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N1C=CC2=C1C=CC=C2

InChI

InChIKey=SIKJAQJRHWYJAI-UHFFFAOYSA-N

InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

HIDE SMILES / InChI

Description
Sources: DOI: 10.5772/62079
Curator's Comment: description was created based on several sources, including: doi: 10.1007/7081_2010_48 http://www.ijpsr.info/docs/IJPSR16-07-02-101.pdf

Indoles and their derivatives are well-known as an important class of heterocyclic compounds, their core being a near-ubiquitous component of biologically active natural products, widespread in different species of plants, animals, and marine organisms. The indole is also well-known as one of the most important scaffolds for drug discovery, capable of serving as ligand for a diverse array of receptors. Indoles is used in textile dyes, perfumes, in agriculture and veterinary medicine. Relatively new areas are dietary supplements and nutraceuticals.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Camphor 5-monooxygenase 1 Target ID: P00183 Gene ID: NA Gene Symbol: camC Target Organism: Pseudomonas putida (Arthrobacter siderocapsulatus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16027900	Substrate 661
Tryptophan synthase beta chain 2 Target ID: P0A879 Gene ID: 945768.0 Gene Symbol: trpB Target Organism: Escherichia coli (strain K12) Sources: https://www.ebi.ac.uk/interpro/entry/IPR006654	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Sleep disorder 20 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c24679cc-4631-46a5-b977-c078a8c08441	Palliative	Approved 8429	INDOLE Approved Use It is used for temporary relief of symptoms of sleep disorders
Nasal sinus congestion 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c24679cc-4631-46a5-b977-c078a8c08441	Palliative	Approved 8429	INDOLE Approved Use It is used for temporary relief of symptoms of nasal sinus congestion
Improper digestion 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c24679cc-4631-46a5-b977-c078a8c08441	Palliative	Approved 8429	INDOLE Approved Use It is used for temporary relief of symptoms of improper digestion

PubMed

Title	Date	PubMed
Preventive effects of an oral sorbent on nephropathy in rats.	1999 Jul-Dec	10681668
Chestnutamide: a novel alkaloid from flowers of Castanea mollissima Blume.	2001	11407819
Fluorescence quenching of anthracene by indole derivatives in phospholipid bilayers.	2001 Apr	11386677
Allosteric free energy changes at the alpha 1 beta 2 interface of human hemoglobin probed by proton exchange of Trp beta 37.	2001 Aug 1	11391770
Phenotypic and genetic characterization of NAD-dependent Pasteurellaceae from the respiratory tract of pigs and their possible pathogenetic importance.	2001 Aug 8	11390108
[Diagnosis of swine dysentery and spirochaetal diarrhea. III. Results of cultural and biochemical differentiation of intestinal Brachyspira species by routine culture from 1997 to 1999].	2001 Feb	11367884
Development of a latex agglutination test for rapid identification of Escherichia coli.	2001 Feb	11305479
Simple indole alkaloids and those with a nonrearranged monoterpenoid unit.	2001 Feb	11245401
Activation of the dienophilicity of indoles in normal electron demand [4 + 2] cycloadditions under high pressure.	2001 Feb 22	11178813
Total syntheses of five indole alkaloids from the marine bryozoan Flustra foliacea.	2001 Feb 23	11312946
Trapping of the putative cationic intermediate in the Morin rearrangement with carbon nucleophiles.	2001 Feb 9	11430103
Truncated trkB.T1 is dominant negative inhibitor of trkB.TK+-mediated cell survival.	2001 Feb 9	11162678
A molecular modeling and 3D QSAR study of a large series of indole inhibitors of human non-pancreatic secretory phospholipase A2.	2001 Jan	11231045
Coronary microvasculature alteration in hypertensive rats. Effect of treatment with a diuretic and an ACE inhibitor.	2001 Jan	11206683
1-Methylindole-3-carboxaldehyde oxime derivatives.	2001 Jan	11173398
The jasmonate-inducible AP2/ERF-domain transcription factor ORCA3 activates gene expression via interaction with a jasmonate-responsive promoter element.	2001 Jan	11169181
Molecular and biochemical analysis of a Madagascar periwinkle root-specific minovincinine-19-hydroxy-O-acetyltransferase.	2001 Jan	11154328
Structural basis for enantiomer binding and separation of a common beta-blocker: crystal structure of cellobiohydrolase Cel7A with bound (S)-propranolol at 1.9 A resolution.	2001 Jan 5	11114249
Synthesis of novel analogues of marine indole alkaloids: mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines as potential anticancer agents.	2001 Jul	11425579
Identification of glucosinolates on the leaf surface of plants from the Cruciferae and other closely related species.	2001 Jul	11397436
Substituted indole-5-carboxamides and -acetamides as potent nonpeptide GnRH receptor antagonists.	2001 Jul 9	11425546
Methyl chanofruticosinates from leaves of Kopsia flavida Blume.	2001 Jun	11394866
Biosynthesis of 2-aminobenzaldehyde in flowers of Robinia pseudoacacia and Philadelphus coronarius.	2001 Jun	11393514
A new and general synthetic pathway to strychnos indole alkaloids: total syntheses of (-)-dehydrotubifoline and (-)-tubifoline by palladium-catalyzed asymmetric allylic substitution.	2001 Jun 14	11405743
Beta D305A mutant of tryptophan synthase shows strongly perturbed allosteric regulation and substrate specificity.	2001 Jun 26	11412095
Catharanthus roseus G-box binding factors 1 and 2 act as repressors of strictosidine synthase gene expression in cell cultures.	2001 Mar	11352466
Thrombopoietic properties of 5-methoxytryptamine plus melatonin versus melatonin alone in the treatment of cancer-related thrombocytopenia.	2001 Mar	11270479
New synthesis of benzo-delta-carbolines, cryptolepines, and their salts: in vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of delta-carbolines, benzo-delta-carbolines, and cryptolepines.	2001 Mar 15	11300877
Dendritic biomimicry: microenvironmental hydrogen-bonding effects on tryptophan fluorescence.	2001 Mar 2	11303878
Calcium/calmodulin-dependent protein kinase inhibition potentiates thapsigargin-mediated cell death in SH-SY5Y human neuroblastoma cells.	2001 Mar 30	11248432
[Sequential isolation of superoxide dismutase and ajmaline from a tissue culture of Rauwolfia serpentina Benth].	2001 Mar-Apr	11357422
Brachycerine, a novel monoterpene indole alkaloid from Psychotria brachyceras.	2001 May	11374976
Lignin peroxidase structure and function.	2001 May	11356137
The role of distal tryptophan in the bifunctional activity of catalase-peroxidases.	2001 May	11356135
Protonation of histidine and histidine-tryptophan interaction in the activation of the M2 ion channel from influenza a virus.	2001 May 22	11352741
Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens.	2001 May 24	11356100
Efficient syntheses of novel C2'-alkylated (+/-)-K252a analogues.	2001 May 31	11405687

Patents

Sample Use Guides

In Vivo Use Guide

1-10 drops under the tongue, 3 times a day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

INDOLE

Systematic Name

English

INDOLE [FCC]

Common Name

English

INDOLE [HSDB]

Common Name

English

INDOLE [MI]

Common Name

English

INDOLE [USP-RS]

Common Name

English

INDOLUM [HPUS]

Common Name

English

INDOLE [FHFI]

Common Name

English

2,3-BENZOPYRROLE

Common Name

English

INDOLUM

Common Name

English

NSC-1964

Code

English

FEMA NO. 2593

Code

English

Classification Tree Code System Code

EPA PESTICIDE CODE

25000