U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H5N
Molecular Weight 67.0892
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRROLE

SMILES

N1C=CC=C1

InChI

InChIKey=KAESVJOAVNADME-UHFFFAOYSA-N
InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H

HIDE SMILES / InChI

Molecular Formula C4H5N
Molecular Weight 67.0892
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

https://translate.google.ru/#view=home&op=translate&sl=en&tl=ru&text=Pyrrole%20is%20a%20five-membered%20aromatic%20heterocyclic%20compound%2C%20which%20contains%20one%20nitrogen%20atom.%20Pyrrole%20is%20a%20colorless%20volatile%20liquid%20that%20darkens%20readily%20upon%20exposure%20to%20air%20and%20is%20usually%20purified%20by%20distillation%20immediately%20before%20use.%20Due%20to%20its%20aromatic%20character%2C%20pyrrole%20is%20difficult%20to%20hydrogenate%2C%20does%20not%20easily%20react%20as%20a%20diene%20in%20Diels%E2%80%93Alder%20reactions%2C%20and%20does%20not%20undergo%20usual%20olefin%20reactions.%20Its%20reactivity%20is%20similar%20to%20that%20of%20benzene%20and%20aniline%2C%20in%20that%20it%20is%20easy%20to%20alkylate%20and%20acylate.%20Under%20acidic%20conditions%2C%20pyrroles%20polymerize%20easily%2C%20and%20thus%20many%20electrophilic%20reagents%20that%20are%20used%20in%20benzene%20chemistry%20are%20not%20applicable%20to%20pyrroles.%20Pyrrole%20and%20its%20derivatives%20(pyrroles)%20are%20widely%20used%20as%20an%20intermediate%20in%20the%20synthesis%20of%20pharmaceuticals%2C%20medicines%2C%20agrochemicals%2C%20dyes%2C%20photographic%20chemicals%2C%20perfumes%2C%20and%20other%20organic%20compounds.%20For%20example%2C%20chlorophyll%20and%20heme%20are%20the%20derivatives%20which%20are%20made%20by%20four%20pyrrole%20ring%20formation%20of%20the%20porphyrin%20ring%20system.%20Pyrrole%20is%20a%20precursor%20to%20the%20nonsteroidal%20anti-inflammatory%20drug%20tolmetin.

Originator

Curator's Comment: F. F. RUNGE detected pyrrole in 1834 as a constituent of coal tar

Approval Year

PubMed

PubMed

TitleDatePubMed
The heme environment of recombinant human indoleamine 2,3-dioxygenase. Structural properties and substrate-ligand interactions.
2002-05-03
Purification and molecular characterization of cGMP-dependent protein kinase from Apicomplexan parasites. A novel chemotherapeutic target.
2002-05-03
Five-coordinate iron(III) porphycenes: (1)H NMR, magnetic, and structural studies.
2002-04-08
Immobilization of glucose oxidase in polypyrrole/polytetrahydrofuran graft copolymers.
2002-04-08
Investigation on the nature of the adsorption sites of pyrrole in alkali-exchanged zeolite y by nuclear magnetic resonance in combination with infrared spectroscopy.
2002-04-03
Heme distortions in sperm-whale carbonmonoxy myoglobin: correlations between rotational strengths and heme distortions in MD-generated structures.
2002-04-03
Determination of thiols by capillary electrophoresis with amperometric detection at a coenzyme pyrroloquinoline quinone modified electrode.
2002-03-15
3-(1H-Pyrrol-1-yl)-2-oxazolidinones as reversible, highly potent, and selective inhibitors of monoamine oxidase type A.
2002-03-14
Missing-link macrocycles: hybrid heterocalixarene analogues formed from several different building blocks.
2002-03-01
Spectroscopy, electrochemistry, and molecular orbital calculations of metal-free tetraazaporphyrin, -chlorin, -bacteriochlorin, and -isobacteriochlorin.
2002-03-01
Porphyrin architectures bearing functionalized xanthene spacers.
2002-02-22
To what extent can aromaticity be defined uniquely?
2002-02-22
Palladium-catalyzed stereocontrolled vinylation of azoles and phenothiazine.
2002-02-21
Phenanthroline complexes bearing fused dipyrrolylquinoxaline anion recognition sites: efficient fluoride anion receptors.
2002-02-20
Minor groove DNA binders as antimicrobial agents. 1. Pyrrole tetraamides are potent antibacterials against vancomycin resistant Enterococci [corrected] and methicillin resistant Staphylococcus aureus.
2002-02-14
A Birch-like mechanism in enzymatic benzoyl-CoA reduction: a kinetic study of substrate analogues combined with an ab initio model.
2002-02-12
Novel photodegradation of the antifungal antibiotic pyrrolnitrin in anhydrous and aqueous aprotic solvents.
2002-02-08
Conversion of L-proline to pyrrolyl-2-carboxyl-S-PCP during undecylprodigiosin and pyoluteorin biosynthesis.
2002-02
A new pyrrole alkaloid from seeds of Castanea sativa.
2002-02
Activation barriers to meso-aryl group rotation in titanyl tetraaryltetrapyrroles. An investigation of the out-of-plane flexibility of hydroporphyrins.
2002-01-28
Water-soluble, core-modified porphyrins as novel, longer-wavelength-absorbing sensitizers for photodynamic therapy. II. Effects of core heteroatoms and meso-substituents on biological activity.
2002-01-17
Observation of an isotope-sensitive low-frequency Raman band specific to metmyoglobin.
2002-01
Strategic issues in reliable sensing.
2002-01
Reagentless biosensing using electrochemical impedance spectroscopy.
2002-01
Polypyrrole-hydrogel composites for the construction of clinically important biosensors.
2002-01
Chromium corroles in four oxidation States.
2001-12-17
Synthesis and biological activity of L-tyrosine-based PPARgamma agonists with reduced molecular weight.
2001-12-17
Theoretical study of stability, structures, and aromaticity of multiply N-confused porphyrins.
2001-12-14
A C-H...O=C hydrogen bond? Intramolecular hydrogen bonding in a novel semirubin.
2001-12-14
Spectrothermodynamic relationship of cationic vs anionic species derived from protonation vs deprotonation of pyrrolo-aza-aromatic bases in homologous series.
2001-12-05
Tetraphenylbenziporphyrin--a ligand for organometallic chemistry.
2001-12-03
Figure-eight tetrathiaoctaphyrin and dihydrotetrathiaoctaphyrin.
2001-12-03
Effects of anticancer drugs on transcription in vitro.
2001-11-29
Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from alpha-amino allenes.
2001-11-29
Promotion of neural cell adhesion by electrochemically generated and functionalized polymer films.
2001-11-15
(2-Fluorophenylimino)tri(1-pyrrolyl)phosphorane.
2001-11
A remarkable skeletal rearrangement of a coordinated tetrapyrrole: chemical consequences of palladium pi-coordination to a bilindione.
2001-10-31
A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-Knorr sequence.
2001-10-18
Single-molecule vibrations, conformational changes, and electronic conductivity of five-membered heterocycles.
2001-10-17
Hypoxia-selective antitumor agents. 16. Nitroarylmethyl quaternary salts as bioreductive prodrugs of the alkylating agent mechlorethamine.
2001-10-11
Formaldehyde oxime <--> nitrosomethane tautomerism.
2001-10-05
DNA structural perturbation induced by the CPI-derived DNA interstrand cross-linker: molecular mechanisms for the sequence specific recognition.
2001-10
Synthesis of porphobilinogen via a novel ozonide cleavage reaction.
2001-09-26
Aromatic dienophiles. 1. A theoretical study of an inverse-electron demand Diels-Alder reaction between 2-aminopyrrole and 1,3,5-triazine.
2001-09-07
Asymmetric total synthesis of ent-(-)-roseophilin: assignment of absolute configuration.
2001-09-05
Studies on DNA cleavage by cytotoxic pyrrole alkaloids reveal the distinctly different behavior of roseophilin and prodigiosin derivatives.
2001-09-03
Dynamic study of metal-ion incorporation into porphyrins based on the dynamic characterization of metal ions and on sitting-atop complex formation.
2001-08
Synthesis and biological evaluation of nonylprodigiosin and macrocyclic prodigiosin analogues.
2001-01-08
Prediction of co-regulated genes in Bacillus subtilis on the basis of upstream elements conserved across three closely related species.
2001
The role of chlorophyll b in photosynthesis: hypothesis.
2001
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:49:12 GMT 2025
Edited
by admin
on Mon Mar 31 18:49:12 GMT 2025
Record UNII
86S1ZD6L2C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRROLE
FCC   FHFI   HSDB  
Systematic Name English
1H-PYRROLE
MI  
Preferred Name English
NSC-62777
Code English
IMIDOLE
Common Name English
1H-PYRROLE [MI]
Common Name English
AZOLE
Systematic Name English
PYRROLE [FHFI]
Common Name English
PYRROLE [FCC]
Common Name English
DIVINYLENIMINE
Common Name English
1-AZA-2,4-CYCLOPENTADIENE
Systematic Name English
FEMA NO. 3386
Code English
PYRROLE [HSDB]
Common Name English
Classification Tree Code System Code
JECFA EVALUATION PYRROLE
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
Code System Code Type Description
CAS
109-97-7
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
NSC
62777
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
JECFA MONOGRAPH
1313
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
HSDB
119
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
EPA CompTox
DTXSID5021910
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
MERCK INDEX
m9398
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY Merck Index
DAILYMED
86S1ZD6L2C
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
CHEBI
35556
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
WIKIPEDIA
PYRROLE
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
FDA UNII
86S1ZD6L2C
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
CHEBI
19203
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-724-7
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
RXCUI
1338938
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY RxNorm
PUBCHEM
8027
Created by admin on Mon Mar 31 18:49:12 GMT 2025 , Edited by admin on Mon Mar 31 18:49:12 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY