Cannabis Compound Database: Showing Compound Card for Pyrrole (CDB005351)

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Record Information

Version

1.0

Created at

2020-04-27 16:11:31 UTC

Updated at

2021-01-04 20:37:39 UTC

CannabisDB ID

CDB005351

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Pyrrole

Description

Pyrrole, C4H4NH, also known as divinyleneimine or monopyrrole, belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing a five-membered ring where a carbon atom is linked to a hetero atom. Substituted derivatives are also called pyrroles such as N-methylpyrrole, C4H4NCH3 or the trisubstituted pyrrole, porphobilinogen. Pyrrole is an essentially neutral compound. It is a colorless volatile liquid that darkens readily upon exposure to air. Pyrrole is found in corn. Pyrrole is a flavouring ingredient. Pyrrole has extremely low basicity compared to conventional amines and some other aromatic compounds like pyridine. This decreased basicity is attributed to the delocalization of the lone pair of electrons of the nitrogen atom in the aromatic ring. Protonation results in loss of aromaticity, and is, therefore, unfavorable. Several syntheses of pyrrole have been described. One example is the Piloty-Robinson pyrrole synthesis which starts with 2 equivalents of an aldehyde and hydrazine and the product is a pyrrole with specific substituents in the 3 and 4 positions. The aldehyde reacts with the diamine to an intermediate di-imine (R C=N N=C R), which, with added hydrochloric acid, gives ring-closure and loss of ammonia to form the pyrrole (¬†doi:10.1002/cber.19100430182). Pyrrole is also a constituent of cannabis smoke. It is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Aza-2,4-cyclopentadiene	ChEBI
Divinyleneimine	ChEBI
Divinylenimine	ChEBI
Imidole	ChEBI
Monopyrrole	ChEBI
Pyrrol	ChEBI
1H-Pyrrole	HMDB
1H-Pyrrole, homopolymer	HMDB
1H-Pyrrole, potassium salt	HMDB
Azole	HMDB
FEMA 3386	HMDB
Indole	HMDB
Polypyrrole	HMDB, MeSH
Pyrolle	HMDB
Pyrrhol	HMDB
Pyrroline	HMDB
Pyrrole	ChEBI
Pyrroles	MeSH

Chemical Formula

C₄H₅N

Average Molecular Weight

67.09

Monoisotopic Molecular Weight

67.0422

IUPAC Name

1H-pyrrole

Traditional Name

pyrrole

CAS Registry Number

109-97-7

SMILES

N1C=CC=C1

InChI Identifier

InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H

InChI Key

KAESVJOAVNADME-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrrole (CHEBI:19203 )
a pyrrole (CPD-13300 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Poaceae

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Anti-inflammatory

Antineoplastic agent:

Antitumor

Household products:

Antimicrobial agent

Biological role:

Nutrient

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-24 °C	Not Available
Boiling Point	129 to 131 °C	Wikipedia
Water Solubility	45 mg/mL at 25 °C	Not Available
logP	0.75	Not Available

Predicted Properties

Property	Value	Source
logP	0.76	ALOGPS
logP	1.05	ChemAxon
logS	0.82	ALOGPS
pKa (Strongest Acidic)	18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.82 m³·mol⁻¹	ChemAxon
Polarizability	7.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00ko-9000000000-8908fc8793c6501dc2d0	2015-03-01	View Spectrum
Predicted GC-MS	Pyrrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-9000000000-f644c5fdd4d5f9db3117	Spectrum
Predicted GC-MS	Pyrrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9000000000-510c084e3c928fa514ae	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9000000000-150b960a1186c02653f7	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9000000000-3bea04ffb045db51356d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxu-9000000000-bb04398351cbc20c433b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-9b747cfdf2fe46d188ee	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-ac61df56d353d5acb48b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-8777c03f1c46a5fcce9d	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9000000000-3f070060c5785123e18c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-3f070060c5785123e18c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02tc-9000000000-43982034e7a3a595201a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9000000000-e0673bc7e6a6226fb72e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9000000000-a3a7192ca6658a081b5b	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-9000000000-972ac9fb6e8cbc34f0d3	2021-09-25	View Spectrum