Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1960)
Drug Name
Phenylethylamine
Synonyms
Benzeneethanamine; Ethanamine, 2-phenyl-; Ethylamine, 2-phenyl-; PHENETHYLAMINE, BETA; Phenethylamine; beta-Aminoethylbenzene; beta-Phenethylamine; beta-Phenylaethylamin [German]; beta-phenylethylamine; phenylethylamine; (2-Aminoethyl)benzene; 1-Amino-2-phenylethane; 1-Phenyl-2-amino-athan; 1-Phenyl-2-aminoethane; 2-Amino-1-phenylethane; 2-Amino-fenylethan; 2-Amino-fenylethan [Czech]; 2-Fenylethylamin; 2-Fenylethylamin [Czech]; 2-Phenethylamine; 2-Phenylethan-1-Amine; 2-Phenylethanamine; 2-phenylethylamine; 64-04-0
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 121.18 Topological Polar Surface Area 26
Heavy Atom Count 9 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
1001
PubChem SID
7711 ; 75923 ; 608001 ; 833519 ; 833521 ; 839990 ; 3135776 ; 5482019 ; 8144848 ; 8150920 ; 10509252 ; 10531461 ; 14747570 ; 24847881 ; 24854450 ; 24865438 ; 24865867 ; 24887854 ; 24887855 ; 24901561 ; 26756723 ; 30280509 ; 32040725 ; 33286030 ; 36523320 ; 46393246 ; 46393335 ; 46393337 ; 47193684 ; 49661414 ; 49718670 ; 49856894 ; 57320659 ; 57652878 ; 57652879 ; 75745031 ; 80953779 ; 85165171 ; 87574348 ; 88519487 ; 92298625 ; 92729694 ; 103185023 ; 103812726 ; 104296483 ; 104667507 ; 117531353 ; 117531423 ; 118307932 ; 124811907
ChEBI ID
CHEBI:18397
CAS Number
64-04-0
TTD Drug ID
D0Q6PI
Formula
C8H11N
Canonical SMILES
C1=CC=C(C=C1)CCN
InChI
1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
InChIKey
BHHGXPLMPWCGHP-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
N-Methylphenylethylamine DM014947
11503
Conjugation - N-methylation 1 [4]
Phenylethanolamin DM014839
1000
Oxidation - Hydroxylation 1 [4]
Unclear DM009999 N. A. Unclear - Unclear 1 [3]
Unclear DM009999 N. A. Unclear - Unclear 1 [2]
N-Methylphenylethanolamine DM014828
913
Conjugation - N-methylation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012694 Phenylethylamine Phenylethanolamin Oxidation - Hydroxylation DBH [4]
MR012696 Phenylethylamine N-Methylphenylethylamine Conjugation - N-methylation Unclear [4]
MR012697 Phenylethylamine Unclear Unclear - Unclear AOC2 ... [2]
MR012695 Phenylethanolamin N-Methylphenylethanolamine Conjugation - N-methylation PNMT [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Copper amine oxidase (AOC3) DME0405 Homo sapiens
AOC3_HUMAN
1.4.3.21
[2]
Monoamine oxidase type A (MAO-A) DME0044 Homo sapiens
AOFA_HUMAN
1.4.3.4
[3]
Semicarbazide-sensitive amine oxidase (AOC2) DME0477 Homo sapiens
AOC2_HUMAN
1.4.3.21
[2]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Semicarbazide-sensitive amine oxidase (AOC2) DME0477 Km = 0.077 microM
AOC2_HUMAN
[2]
Copper amine oxidase (AOC3) DME0405 Km = 0.077 microM
AOC3_HUMAN
[2]
Monoamine oxidase type A (MAO-A) DME0044 Km = 0.35 microM
AOFA_HUMAN
[3]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 2144).
2 The unique substrate specificity of human AOC2, a semicarbazide-sensitive amine oxidase. Cell Mol Life Sci. 2009 Aug;66(16):2743-57.
3 Do monomeric vs dimeric forms of MAO-A make a difference? A direct comparison of the catalytic properties of rat and human MAO-A's. J Neural Transm (Vienna). 2007;114(6):721-4.
4 Discriminative stimulus properties of beta-phenylethylamine, deuterated beta-phenylethylamine, phenylethanolamine and some metabolites of phenylethylamine in rodents

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