Cannabis Compound Database: Showing Compound Card for Phenylethylamine (CDB000126)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (6) Show 9 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:25:44 UTC

Updated at

2022-12-13 23:36:23 UTC

CannabisDB ID

CDB000126

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Phenylethylamine

Description

Phenylethylamine (PEA) is an aromatic amine which has a constitutional isomer (+)-phenylethylamine (1-phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. It is a strongly basic, colorless liquid at room temperature which is soluble in water, ethanol, and ether. Similar to other low-molecular-weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate salt with carbon dioxide. Phenylethylamines can be biosynthesized in mammals from the amino acid phenylalanine by enzymatic decarboxylation. Phenylethylamine is produced after microbial fermentation and is a metabolite of Bacillus, Enterococcus, Pseudomanas and Lactobacillus (PMID: 22953951 ; PMID: 17307265 ; PMID: 16630269 ) and has anti-microbial properties against pathogenic strains of E. coli. It is found in many foods such as chocolate. However, trace amounts from food are quickly metabolized by the enzyme monoamine oxidase (MAO-B) into phenylacetic acid, preventing significant concentrations from reaching the brain. In the human brain, phenylethylamine is a central nervous system stimulant that binds to the human trace amine-associated receptor 1¬†(hTAAR1) as an¬†agonist (PMID: 27424325 ). It is a precursor to the neurotransmitter phenylethanolamine. High levels of PEA have been found in the urine of schizophrenics, but it is not significantly elevated in the serum or CSF of schizophrenics (PMID: 7906896 , PMID: 7360842 ). Urinary levels of PEA are significantly lower in children with attention deficit hyperactivity disorder (ADHD) (PMID: 12205654 ). Phenylethylamine is also a skin irritant and possible sensitizer. PEA is the primary compound found in carnivore urine (especially cat) that repels mice and rats. Quantitative HPLC analysis across 38 mammalian species has shown that PEA production in urine is especially high in carnivores, with some producing >3,000-fold more than herbivores (PMID: 21690383 ). PEA is also found in Cannabis plants (PMID: 6991645 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Benzeneethanamine	ChEBI
beta-Aminoethylbenzene	ChEBI
beta-Phenethylamine	ChEBI
beta-Phenylethylamine	ChEBI
Phenethylamine	ChEBI
2-Phenylethylamine	Kegg
b-Aminoethylbenzene	Generator
Β-aminoethylbenzene	Generator
b-Phenethylamine	Generator
Β-phenethylamine	Generator
b-Phenylethylamine	Generator
Β-phenylethylamine	Generator
(2-Aminoethyl)benzene	HMDB
(2-Aminoethyl)polystyrene	HMDB
1-amino-2-Phenylethane	HMDB
1-Phenethylamine	HMDB
1-Phenyl-2-amino-athan	HMDB
1-Phenyl-2-aminoethane	HMDB
1TNJ	HMDB
1Utm	HMDB
1Uto	HMDB
2-amino-1-Phenylethane	HMDB
2-amino-Fenylethan	HMDB
2-Fenylethylamin	HMDB
2-Phenethylamine	HMDB, MeSH
2-Phenyl-ethanamine	HMDB
2-Phenylethanamine	HMDB
2-Phenylethanamine (acd/name 4.0)	HMDB
2-Phenylethylamine (acd/name 4.0)	HMDB
b-Phenylaethylamin	HMDB
Benzeneethanamine hydrochloride	HMDB
beta Phenethylamine	HMDB
beta-Phenylaethylamin	HMDB
Omega-phenylethylamine	HMDB
PEA	HMDB
Phenethylamine hydrochloride	HMDB, MeSH
Polystyrene a-NH2	HMDB
Phenethylamine hydrobromide	MeSH, HMDB
Phenethylamine tosylate	MeSH, HMDB
Phenethylamine conjugate acid	MeSH, HMDB
Phenethylamine sulfate	MeSH, HMDB
Phenethylamine, monolithium salt	MeSH, HMDB
2-Phenylethylammonium chloride	MeSH, HMDB
Phenethylamine sulfate (2:1)	MeSH, HMDB
Phenethylamine, 15N-labeled CPD	MeSH, HMDB
Phenethylamine mesylate	MeSH, HMDB
Phenethylamine perchlorate	MeSH, HMDB
Phenethylamine, beta-(14)C-labeled CPD	MeSH, HMDB
Diphenethylamine sulfate	MeSH, HMDB

Chemical Formula

C₈H₁₁N

Average Molecular Weight

121.18

Monoisotopic Molecular Weight

121.0891

IUPAC Name

2-phenylethan-1-amine

Traditional Name

2-phenylethylamine

CAS Registry Number

64-04-0

SMILES

NCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2

InChI Key

BHHGXPLMPWCGHP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
2-arylethylamine
Aralkylamine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alkaloid (CHEBI:18397 )
aralkylamine (CHEBI:18397 )
phenylethylamine (CHEBI:18397 )
Biogenic amines (C05332 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Skin irritant

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Animal

Microbe:

Lactobacillus:

Bacillus:

Bacillus subtilis

Enterococcus:

Enterococcus faecium

Plant:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.41	ALOGPS
logP	1.39	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39.29 m³·mol⁻¹	ChemAxon
Polarizability	14.35 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)	splash10-001i-9000000000-bf5d1e8f4a14683bd0aa	2015-03-01	View Spectrum
GC-MS	Phenylethylamine, 1 TMS, GC-MS Spectrum	splash10-0udi-3900000000-c931498c67dbf88820ee	Spectrum
GC-MS	Phenylethylamine, 2 TMS, GC-MS Spectrum	splash10-00dr-5900000000-d15a3c803d2534e366d8	Spectrum
GC-MS	Phenylethylamine, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-7713ab7346491f1f5f42	Spectrum
GC-MS	Phenylethylamine, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-94774bbd6283b4a26a51	Spectrum
GC-MS	Phenylethylamine, non-derivatized, GC-MS Spectrum	splash10-0abc-5900000000-724c680a9564ac27f7ee	Spectrum
GC-MS	Phenylethylamine, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-5ba434a8565ec0014b6b	Spectrum
GC-MS	Phenylethylamine, non-derivatized, GC-MS Spectrum	splash10-053r-9000000000-f312ab6fe99f8eca86e7	Spectrum
GC-MS	Phenylethylamine, non-derivatized, GC-MS Spectrum	splash10-0udi-3900000000-c931498c67dbf88820ee	Spectrum
GC-MS	Phenylethylamine, non-derivatized, GC-MS Spectrum	splash10-00dr-5900000000-d15a3c803d2534e366d8	Spectrum
GC-MS	Phenylethylamine, non-derivatized, GC-MS Spectrum	splash10-00dr-4900000000-4c37abb4c50d5582d87c	Spectrum
Predicted GC-MS	Phenylethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001l-9100000000-3e2562db471b8bb298d2	Spectrum
Predicted GC-MS	Phenylethylamine, 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-QTOF , positive	splash10-00di-0900000000-95c5a1366bba1014e2aa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-0900000000-5ad03d29c0ff6167539c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0900000000-1b25fe0d03af3ce715ba	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-056r-7900000000-a6478bab1f5bd04c7329	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9100000000-abdacae4bceb2048614f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-d61f8f9b0d593297d010	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-0900000000-e3d2be06e661bac2f739	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0900000000-fc4c40ae6333ed1f04f6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-056r-7900000000-f25cc18055d08500ec9d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9100000000-0e8ece94eaa349e6fd21	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0uk9-2900000000-272fff4a446fcf053de8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-e833e9ebdd0584ee9cff	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-f51c34f8fd6e67925a52	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-162188a06251a43ccc54	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-162188a06251a43ccc54	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-2a12817c62551d9dee50	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-ac8b555024a8bbc5e78b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-926231c14695be35af04	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-c5e8005c53eaf96bc957	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-6f9e6a6eb6c2ac8f4531	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-1900000000-aeb026a07351a147ae19	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-3900000000-a6c6357f047322c4efe1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a6r-6900000000-0a32d01e2dda19a78c83	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-056r-9600000000-be832e76b1211d35978c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-004i-9400000000-ab97002137a57a7802bc	2017-09-14	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Serotonin N-acetyltransferase	AANAT	17q25	Q16613	details
Amine oxidase [flavin-containing] B	MAOB	Xp11.23	P27338	details
Amine oxidase [flavin-containing] A	MAOA	Xp11.3	P21397	details
Aromatic-L-amino-acid decarboxylase	DDC	7p12.2	P20711	details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Trace amine-associated receptor 1	TAAR1	6q23.2	Q96RJ0	details

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.000118 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.000702 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.0000749 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.000205 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.0000487 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.000137 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0012275

DrugBank ID

DB04325

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

2-phenylethylamine

METLIN ID

Not Available

PubChem Compound

1001

PDB ID

Not Available

ChEBI ID

18397

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Kim B, Byun BY, Mah JH: Biogenic amine formation and bacterial contribution in Natto products. Food Chem. 2012 Dec 1;135(3):2005-11. doi: 10.1016/j.foodchem.2012.06.091. Epub 2012 Jul 3. [PubMed:22953951 ]
Landete JM, Pardo I, Ferrer S: Tyramine and phenylethylamine production among lactic acid bacteria isolated from wine. Int J Food Microbiol. 2007 Apr 20;115(3):364-8. doi: 10.1016/j.ijfoodmicro.2006.10.051. Epub 2007 Jan 18. [PubMed:17307265 ]
Marcobal A, de las Rivas B, Munoz R: First genetic characterization of a bacterial beta-phenylethylamine biosynthetic enzyme in Enterococcus faecium RM58. FEMS Microbiol Lett. 2006 May;258(1):144-9. doi: 10.1111/j.1574-6968.2006.00206.x. [PubMed:16630269 ]
Khan MZ, Nawaz W: The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system. Biomed Pharmacother. 2016 Oct;83:439-449. doi: 10.1016/j.biopha.2016.07.002. Epub 2016 Jul 15. [PubMed:27424325 ]
O'Reilly RL, Davis BA: Phenylethylamine and schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 1994 Jan;18(1):63-75. doi: 10.1016/0278-5846(94)90024-8. [PubMed:7906896 ]
Potkin SG, Wyatt RJ, Karoum F: Phenylethylamine (PEA) and phenylacetic acid (PAA) in the urine of chronic schizophrenic patients and controls. Psychopharmacol Bull. 1980 Jan;16(1):52-4. [PubMed:7360842 ]
Kusaga A, Yamashita Y, Koeda T, Hiratani M, Kaneko M, Yamada S, Matsuishi T: Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. Ann Neurol. 2002 Sep;52(3):372-4. doi: 10.1002/ana.10302. [PubMed:12205654 ]
Ferrero DM, Lemon JK, Fluegge D, Pashkovski SL, Korzan WJ, Datta SR, Spehr M, Fendt M, Liberles SD: Detection and avoidance of a carnivore odor by prey. Proc Natl Acad Sci U S A. 2011 Jul 5;108(27):11235-40. doi: 10.1073/pnas.1103317108. Epub 2011 Jun 20. [PubMed:21690383 ]

Enzymes

Enzyme Details

1. Serotonin N-acetyltransferase

General function:: Involved in N-acetyltransferase activity
Specific function:: Controls the night/day rhythm of melatonin production in the pineal gland. Catalyzes the N-acetylation of serotonin into N-acetylserotonin, the penultimate step in the synthesis of melatonin.
Gene Name:: AANAT
Uniprot ID:: Q16613
Molecular weight:: 23343.8

Enzyme Details

2. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Enzyme Details

3. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Enzyme Details

4. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Enzyme Details

5. Membrane primary amine oxidase

General function:: Involved in copper ion binding
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:: AOC3
Uniprot ID:: Q16853
Molecular weight:: 84621.27

Enzyme Details

6. Retina-specific copper amine oxidase

General function:: Involved in copper ion binding
Specific function:: Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:: AOC2
Uniprot ID:: O75106
Molecular weight:: 80515.11

Showing Compound Card for Phenylethylamine (CDB000126)

Structure for CDB000126 (Phenylethylamine)

Enzymes