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

Molecular Formula	C8H7N
Molecular Weight	117.1479
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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	Potency
Amine oxidase [flavin-containing] A 14 Target ID: P21397 Gene ID: 4128.0 Gene Symbol: MAOA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8304974	Inhibitor 8504	0.4 µM [Ki]
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 25 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c24679cc-4631-46a5-b977-c078a8c08441	Palliative	Approved 8583	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 8583	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 8583	INDOLE Approved Use It is used for temporary relief of symptoms of improper digestion

PubMed

Title	Date	PubMed
Phenotypic and genetic characterization of NAD-dependent Pasteurellaceae from the respiratory tract of pigs and their possible pathogenetic importance.	2001-08-08	11390108
Allosteric free energy changes at the alpha 1 beta 2 interface of human hemoglobin probed by proton exchange of Trp beta 37.	2001-08-01	11391770
Substituted indole-5-carboxamides and -acetamides as potent nonpeptide GnRH receptor antagonists.	2001-07-09	11425546
Dynamic features of the subunit interface of Cu,Zn superoxide dismutase as probed by tryptophan phosphorescence.	2001-07-01	11414691
Synthesis of novel analogues of marine indole alkaloids: mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines as potential anticancer agents.	2001-07	11425579
Modification of voltage-dependent gating of potassium channels by free form of tryptophan side chain.	2001-07	11423398
Proteins with beta-(thienopyrrolyl)alanines as alternative chromophores and pharmaceutically active amino acids.	2001-07	11420430
Identification of glucosinolates on the leaf surface of plants from the Cruciferae and other closely related species.	2001-07	11397436
Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction.	2001-06-29	11421771
Applications of vinylogous Mannich reactions. Total syntheses of the Ergot alkaloids rugulovasines A and B and setoclavine.	2001-06-27	11414824
Synthesis of ent-alantrypinone.	2001-06-27	11414821
3-Methyleneoxindole: an affinity label of glutathione S-transferase pi which targets tryptophan 38.	2001-06-26	11412109
Beta D305A mutant of tryptophan synthase shows strongly perturbed allosteric regulation and substrate specificity.	2001-06-26	11412095
Transformation of a kappa-opioid receptor antagonist to a kappa-agonist by transfer of a guanidinium group from the 5'- to 6'-position of naltrindole.	2001-06-21	11405645
A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes.	2001-06-15	11403851
Incorporation of beta-selenolo[3,2-b]pyrrolyl-alanine into proteins for phase determination in protein X-ray crystallography.	2001-06-15	11399069
A new and general synthetic pathway to strychnos indole alkaloids: total syntheses of (-)-dehydrotubifoline and (-)-tubifoline by palladium-catalyzed asymmetric allylic substitution.	2001-06-14	11405743
Intermolecular and intramolecular Diels-Alder cycloadditions of 3-ylidenepiperazine-2,5-diones and 5-acyloxy-2(1h)-pyrazinones.	2001-06-01	11375024
Effects of indole on breathing in rats.	2001-06	11399929
Methyl chanofruticosinates from leaves of Kopsia flavida Blume.	2001-06	11394866
Biosynthesis of 2-aminobenzaldehyde in flowers of Robinia pseudoacacia and Philadelphus coronarius.	2001-06	11393514
Efficient syntheses of novel C2'-alkylated (+/-)-K252a analogues.	2001-05-31	11405687
Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens.	2001-05-24	11356100
Protonation of histidine and histidine-tryptophan interaction in the activation of the M2 ion channel from influenza a virus.	2001-05-22	11352741
Thiazole analogues of the NSAID indomethacin as selective COX-2 inhibitors.	2001-05-21	11392547
[Sequential isolation of superoxide dismutase and ajmaline from a tissue culture of Rauwolfia serpentina Benth].	2001-05-19	11357422
Synthesis of tricyclic indole-2-carboxylic [correction of caboxylic] acids as potent NMDA-glycine antagonists.	2001-05-18	11348132
Novel bone antiresorptive agents that selectively inhibit the osteoclast V-H+-ATPase.	2001-05-12	11347950
2-Aryl indole NK1 receptor antagonists: optimisation of indole substitution.	2001-05-07	11354384
Insights into the genetic diversity of initial dioxygenases from PAH-degrading bacteria.	2001-05	11414329
Porphyromonas gulae sp. nov., an anaerobic, gram-negative coccobacillus from the gingival sulcus of various animal hosts.	2001-05	11411686
Revision of the structure of ajmalimine.	2001-05	11374979
Brachycerine, a novel monoterpene indole alkaloid from Psychotria brachyceras.	2001-05	11374976
Lignin peroxidase structure and function.	2001-05	11356137
The role of distal tryptophan in the bifunctional activity of catalase-peroxidases.	2001-05	11356135
N-Methyl-N-(1-phenylsulfonylindol-2-ylmethyl)aniline.	2001-05	11353254
A new synthetic method for preparing indole derivatives from 2-keto glycosides.	2001-04-12	11383891
Fluorescence quenching of anthracene by indole derivatives in phospholipid bilayers.	2001-04	11386677
Malassezin--A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur.	2001-04	11354679
DNA binding properties of the marine sponge pigment fascaplysin.	2001-04	11354674
Synthesis, pharmacological characterization and QSAR studies on 2-substituted indole melatonin receptor ligands.	2001-04	11354661
The role of tryptophan in the antibacterial activity of a 15-residue bovine lactoferricin peptide.	2001-04	11354462
The positive inotropic and chronotropic effects of evodiamine and rutaecarpine, indoloquinazoline alkaloids isolated from the fruits of Evodia rutaecarpa, on the guinea-pig isolated right atria: possible involvement of vanilloid receptors.	2001-04	11345696
The oxidation of indole derivatives catalyzed by horseradish peroxidase is highly chemiluminescent.	2001-03-15	11370838
Catharanthus roseus G-box binding factors 1 and 2 act as repressors of strictosidine synthase gene expression in cell cultures.	2001-03	11352466
Trapping of the putative cationic intermediate in the Morin rearrangement with carbon nucleophiles.	2001-02-09	11430103
[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].	2001-02	11367884
Enantioselective construction of cyclic quaternary centers: (-)-mesembrine.	2001-01-12	11429891
Chestnutamide: a novel alkaloid from flowers of Castanea mollissima Blume.	2001	11407819
Regulation of prostaglandin synthesis and cell adhesion by a tryptophan catabolizing enzyme.	2001	11375052

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:44 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:44 GMT 2025`
Record UNII	8724FJW4M5
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

INDOLE

Systematic Name

English

INDOLUM

Preferred 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

NSC-1964

Code

English

FEMA NO. 2593

Code

English

Classification Tree Code System Code

EPA PESTICIDE CODE

25000