Cannabis Compound Database: Showing Compound Card for Diphenylamine (CDB005711)

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Record Information

Version

1.0

Created at

2020-04-27 16:48:02 UTC

Updated at

2021-01-04 18:49:10 UTC

CannabisDB ID

CDB005711

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Diphenylamine

Description

Diphenylamine, also known as DPA or anilinobenzene, belongs to the class of organic compounds known as anilines and substituted anilines. These are organic compounds containing an aminobenzene moiety. Diphenylamine consists of an amine bound to two phenyl groups. It exists as a colorless solid, but commercial samples are often yellow due to oxidized impurities ( Ref:DOI ). It dissolves well in many common organic solvents and is moderately soluble in water. It has a sweet floral odor. Diphenylamine is used mainly for its antioxidant properties and is widely used as an industrial antioxidant, dye mordant and reagent. DPA and derivatives are most commonly used as stabilizers in nitrocellulose-containing explosives and propellants, in the perfumery, and as antioxidants in the rubber and elastomer industry (PMID: 14505701 ). It is also employed in agriculture as a fungicide and antihelmintic. Diphenylamine is found naturally in a number of foods with the highest concentration being found in garden onions. Diphenylamine has also been detected, but not quantified in, several different foods, such as corianders, lemons, tea, and wild celeries. This could make diphenylamine a potential biomarker for the consumption of these foods. Diphenylamine is used as a plant growth regulator and as a pre- or postharvest scald inhibitor for apples. Its anti-scald activity is the result of its antioxidant properties, which protect the apple skin from the oxidation products of α-farnesene during storage ( PMID: 16218691 ). Diphenylamine is a potentially toxic compound. In animal experiments diphenylamine has been found to be rapidly and completely absorbed after oral ingestion. It is rapidly excreted mainly via urine. Acute oral and dermal toxicity are low. However, Diphenylamine can cause severe irritation to the eyes. Diphenylamine has been shown in animal studies to target the red blood cell system and can cause abnormal erythropoiesis in the spleen, and thus congestion of the spleen, and haemosiderosis. Diphenylamine is a constituent of marijuana (cannabis) smoke and is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(Phenylamino)benzene	ChEBI
Anilinobenzene	ChEBI
C6H5-NH-C6H5	ChEBI
DPA	ChEBI
N,N-Diphenylamine	ChEBI
N-Phenylbenzenamine	ChEBI
(phenylamino)-Benzene	HMDB
2-Biphenylyl-N-pyridyl-acetamide	HMDB
2-Biphenylyl-N-pyridylacetamide	HMDB
anilino-Benzene	HMDB
Benzenamine, N-phenyl-, styrenated	HMDB
Big dipper	HMDB
Deccoscald 282	HMDB
DFA	HMDB
Difenylamin	HMDB
Diphenpyramide	HMDB
Diphenyl-amine	HMDB
Diphenylamine indicator	HMDB
Diphenylamine, acs	HMDB
Diphenylamine, reaction product with 2,2,4-trimethylpentene	HMDB
N-Fenylanilin	HMDB
N-Phenyl-aniline	HMDB
N-Phenyl-benzenamine	HMDB
N-Phenylbenzenamine, 9ci	HMDB
N-Phenylbenzenamine, styrenated	HMDB
N-Phenylbenzeneamine	HMDB
Naugalube 428l	HMDB
no Scald	HMDB
no Scald dpa 283	HMDB
NO-Scald	HMDB
NO-Scald dpa 283	HMDB
Phenylaniline	HMDB
Poly(diphenylamine)	HMDB
Pyridyl-biphenylyl-acetamide	HMDB
Scaldip	HMDB
Shield dpa	HMDB
Styrenated diphenylamine	HMDB
Styrene, reaction product with diphenylamine	HMDB

Chemical Formula

C₁₂H₁₁N

Average Molecular Weight

169.22

Monoisotopic Molecular Weight

169.0891

IUPAC Name

N-phenylaniline

Traditional Name

diphenylamine

CAS Registry Number

122-39-4

SMILES

N(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H

InChI Key

DMBHHRLKUKUOEG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline and substituted anilines

Alternative Parents

Substituents

Aniline or substituted anilines
Secondary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:4640 )
aromatic amine (CHEBI:4640 )
bridged diphenyl fungicide (CHEBI:4640 )
a small molecule (CPD-9937 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Biofluid and excreta:

Saliva

Role

Environmental role:

Biological role:

Antioxidant

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	52 - 54 °C	Not Available
Boiling Point	302 °C	Wikipedia
Water Solubility	0.053 mg/mL at 20 °C	Not Available
logP	3.50	Not Available

Predicted Properties

Property	Value	Source
logP	3.34	ALOGPS
logP	3.41	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.54 m³·mol⁻¹	ChemAxon
Polarizability	19.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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)	splash10-014i-5900000000-8c8ae83e5ede4467297a	2014-09-20	View Spectrum
GC-MS	Diphenylamine, non-derivatized, GC-MS Spectrum	splash10-014i-2900000000-0f2d7d76998f0e03ab74	Spectrum
GC-MS	Diphenylamine, non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-86a150c3e0c06fd6c431	Spectrum
GC-MS	Diphenylamine, non-derivatized, GC-MS Spectrum	splash10-014i-8900000000-43ff93288efd91fa24fd	Spectrum
GC-MS	Diphenylamine, non-derivatized, GC-MS Spectrum	splash10-014i-2900000000-0f2d7d76998f0e03ab74	Spectrum
GC-MS	Diphenylamine, non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-86a150c3e0c06fd6c431	Spectrum
GC-MS	Diphenylamine, non-derivatized, GC-MS Spectrum	splash10-014i-8900000000-43ff93288efd91fa24fd	Spectrum
Predicted GC-MS	Diphenylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-2900000000-95ad298f6a9717294697	Spectrum
Predicted GC-MS	Diphenylamine, 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	splash10-00di-0900000000-336cf3dcad8a94f8f2fe	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0900000000-17db2a0cdb58bb5824c3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-3900000000-2a0efcae7cb8dd177041	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-006x-9800000000-e79da21524f340fefcd4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0006-9200000000-d3f71eb25d134e12dec6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0006-9100000000-5dfcdb1d8c44264cc153	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0900000000-2283250c2cf8e7fdffbd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-2900000000-3a5b94cdf663cbe3bc48	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9200000000-797a3103a29e18b04c1c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-cbc979c9a66db9d0b5c4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-f417cc3873e4f1ad2c80	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-00di-0900000000-cf90bb96548b3a94c35b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-00di-2900000000-76156abb74c363853359	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9300000000-30558c8720d9f497b7e0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9200000000-5838e4d5ff5e8f3a9323	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9200000000-9d965a101be070305d88	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-00di-0900000000-2228916b18e1afebcbc6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-00di-0900000000-12e21d12706763f57b90	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-00dl-4900000000-f2aab9a54df33c3c9126	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-00c2a79f600db264c67d	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-3f72bbc5daf7c9fd9558	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v4l-9700000000-f5a6b692c949f5a02f60	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-10096022c5cd3d396374	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-899ac00162614581a441	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-5900000000-4f65d69ee98d44ec919f	2016-08-03	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0032562

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010494

KNApSAcK ID

Not Available

Chemspider ID

11003

KEGG Compound ID

C11016

BioCyc ID

CPD-9937

BiGG ID

Not Available

Wikipedia Link

Diphenylamine

METLIN ID

Not Available

PubChem Compound

11487

PDB ID

Not Available

ChEBI ID

4640

References

General References

Drzyzga O: Diphenylamine and derivatives in the environment: a review. Chemosphere. 2003 Dec;53(8):809-18. doi: 10.1016/S0045-6535(03)00613-1. [PubMed:14505701 ]
Rudell DR, Mattheis JP, Fellman JK: Relationship of superficial scald development and alpha-farnesene oxidation to reactions of diphenylamine and diphenylamine derivatives in Cv. Granny Smith apple peel. J Agric Food Chem. 2005 Oct 19;53(21):8382-9. doi: 10.1021/jf0512407. [PubMed:16218691 ]

Showing Compound Card for Diphenylamine (CDB005711)

Structure for CDB005711 (Diphenylamine)