General Information of Drug (ID: DMX0G4F)

Drug Name
PHENETHYLAMINE Drug Info
Synonyms
Phenethylamine; 2-phenylethylamine; 2-Phenylethanamine; 64-04-0; Benzeneethanamine; phenylethylamine; 2-Phenethylamine; beta-phenylethylamine; beta-Phenethylamine; 1-Amino-2-phenylethane; beta-Aminoethylbenzene; (2-Aminoethyl)benzene; 2-Amino-1-phenylethane; 1-Phenyl-2-aminoethane; Ethylamine, 2-phenyl-; Ethanamine, 2-phenyl-; 2-Phenylethan-1-Amine; 1-Phenyl-2-amino-athan; 2-Fenylethylamin; 2-Amino-fenylethan; 2-Fenylethylamin [Czech]; PHENETHYLAMINE, BETA; 2-Amino-fenylethan [Czech]; beta-Phenylaethylamin [German]
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
1001
ChEBI ID
CHEBI:18397
CAS Number
CAS 64-04-0
TTD Drug ID
DMX0G4F
INTEDE Drug ID
DR1960

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Discontinued Drug(s)
Drug(s) Targeting 5-HT 2A receptor (HTR2A)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Metergolin DMJFP6G Hyperprolactinaemia 5A60.1 Approved [9]
ZOTEPINE DMF3VXA Anxiety disorder 6B00-6B0Z Approved [10]
Iloperidone DM6AUFY Schizophrenia 6A20 Approved [11]
Flibanserin DM70DTN Depression 6A70-6A7Z Approved [12]
Lurasidone hydrochloride DMCVPXO Schizophrenia 6A20 Approved [13]
Aniracetam DMOIFW0 Cerebrovascular ischaemia 8B1Z Approved [14]
lumateperone tosylate DMQ8HOJ Schizophrenia 6A20 Approved [15]
Sarpogrelate DMGLP6S Diabetic complication 5A2Y Approved [16]
Pimavanserin DMR7IVC Parkinson disease 8A00.0 Approved [17]
Zicronapine DMP8ESD Schizophrenia 6A20 Phase 3 [18]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Monoamine oxidase type A (MAO-A)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Epinephrine DM3KJBC Acute asthma CA23 Approved [19]
Zolmitriptan DM1IB4Q Migraine 8A80 Approved [20]
Naratriptan DMO50U2 Headache 8A80-8A84 Approved [21]
Safinamide mesylate DM0J2ZT Parkinson disease 8A00.0 Approved [22]
Almotriptan malate DMFG5ST N. A. N. A. Approved [23]
SEROTONIN DMOFCRY Discovery agent N.A. Investigative [3]
Benzylamine DMRM6ES N. A. N. A. Investigative [3]
⏷ Show the Full List of 7 Drug(s)
Drug(s) Metabolized By Copper amine oxidase (AOC3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tresperimus DMOVBSF Autoimmune diabetes 5A10 Discontinued in Phase 3 [24]
tyramine DM4UXT1 Discovery agent N.A. Investigative [4]
Benzylamine DMRM6ES N. A. N. A. Investigative [4]
Methylamine DMTPL4W N. A. N. A. Investigative [4]
Drug Name Drug ID Indication ICD 11 Highest Status REF
tyramine DM4UXT1 Discovery agent N.A. Investigative [4]
Benzylamine DMRM6ES N. A. N. A. Investigative [4]
Methylamine DMTPL4W N. A. N. A. Investigative [4]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [25]
Ifosfamide DMCT3I8 Adult central nervous system germ cell tumor Approved [26]
Rilmenidine DM13PQW Hypertension BA00-BA04 Approved [27]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [28]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [29]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [30]
Oxymetazoline DM8ZXT6 Arrhythmia BC9Z Approved [31]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [32]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [33]
Indapamide DMGN1PW Edema MG29 Approved [34]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Selenium DM25CGV N. A. N. A. Approved [35]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [36]
Oxymetazoline DM8ZXT6 Arrhythmia BC9Z Approved [31]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [33]
Dexamethasone DMMWZET Acute adrenal insufficiency Approved [37]
Cupric Sulfate DMP0NFQ Fungal infection 1F29-1F2F Approved [38]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [39]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [40]
Vorinostat DMWMPD4 Adult acute monocytic leukemia Approved [41]
Xylometazoline DMKV32D Allergic rhinitis CA08.0 Phase 4 [31]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
TRYPTAMINE DMAFPHB N. A. N. A. Phase 3 [8]
Octopamine DMLQVTJ Thrombosis DB61-GB90 Discontinued in Phase 2a [8]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dopamine DMPGUCF Acromegaly 5A60.0 Approved [42]
Amphetamine DMSZQAK Attention deficit hyperactivity disorder 6A05.Z Approved [43]
Bupropion DM5PCS7 Depression 6A70-6A7Z Approved [44]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [45]
Testosterone DM7HUNW Hot flushes GA30 Approved [46]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [46]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [33]
Dextroamphetamine DMMIHVP Attention deficit hyperactivity disorder 6A05.Z Approved [47]
Vorinostat DMWMPD4 Adult acute monocytic leukemia Approved [41]
Permethrin DMZ0Q1G Pediculus capitis infestation 1G00.0 Approved [48]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Procainamide DMNMXR8 Ventricular arrhythmias BC71 Approved [49]
Hydralazine DMU8JGH Chronic heart failure BD1Z Approved [50]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [51]
Sulfamethoxazole DMB08GE Acute otitis media AB00 Approved [52]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [53]
Quercetin DM3NC4M Obesity 5B81 Approved [54]
Testosterone DM7HUNW Hot flushes GA30 Approved [46]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [55]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [56]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [57]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 2A receptor (HTR2A) TTJQOD7 5HT2A_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Monoamine oxidase type A (MAO-A) DERE4TU AOFA_HUMAN Substrate [3]
Copper amine oxidase (AOC3) DE6SOC5 AOC3_HUMAN Substrate [4]
Semicarbazide-sensitive amine oxidase (AOC2) DE8DP90 AOC2_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Alpha-2A adrenergic receptor (ADRA2A) OTZFGOTP ADA2A_HUMAN Protein Interaction/Cellular Processes [5]
Alpha-2C adrenergic receptor (ADRA2C) OT5B9RKP ADA2C_HUMAN Protein Interaction/Cellular Processes [5]
Arylamine N-acetyltransferase 2 (NAT2) OTBPDQOY ARY2_HUMAN Biotransformations [6]
Sodium-dependent dopamine transporter (SLC6A3) OT39XG28 SC6A3_HUMAN Regulation of Drug Effects [7]
Trace amine-associated receptor 1 (TAAR1) OTUY8CGM TAAR1_HUMAN Gene/Protein Processing [8]

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2144).
2 Exploring the relationship between binding modes of 9-(aminomethyl)-9,10-dihydroanthracene and cyproheptadine analogues at the 5-HT2A serotonin rec... Bioorg Med Chem Lett. 2001 Feb 26;11(4):563-6.
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 The unique substrate specificity of human AOC2, a semicarbazide-sensitive amine oxidase. Cell Mol Life Sci. 2009 Aug;66(16):2743-57.
5 Effects of synephrine and beta-phenethylamine on human alpha-adrenoceptor subtypes. Planta Med. 2010 Jul;76(10):981-6. doi: 10.1055/s-0029-1240884. Epub 2010 Mar 9.
6 N-acetyltransferase 2 genetic polymorphism modifies genotoxic and oxidative damage from new psychoactive substances. Arch Toxicol. 2023 Jan;97(1):189-199. doi: 10.1007/s00204-022-03383-2. Epub 2022 Sep 23.
7 Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. doi: 10.1124/jpet.105.084459. Epub 2005 Mar 11.
8 Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands. Biochem J. 2009 Oct 23;424(1):39-45. doi: 10.1042/BJ20090998.
9 Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. Naunyn Schmiedebergs Arch Pharmacol. 2004 Aug;370(2):114-23.
10 Current and novel approaches to the drug treatment of schizophrenia. J Med Chem. 2001 Feb 15;44(4):477-501.
11 Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.
12 Radium 223 dichloride for prostate cancer treatment. Drug Des Devel Ther. 2017 Sep 6;11:2643-2651.
13 Mullard A: 2010 FDA drug approvals. Nat Rev Drug Discov. 2011 Feb;10(2):82-5.
14 Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43.
15 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
16 Beneficial effects of sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, supplemented with pioglitazone on diabetic model mice. Endocr Res. 2009;34(1-2):18-30.
17 Pimavanserin, a selective serotonin (5-HT)2A-inverse agonist, enhances the efficacy and safety of risperidone, 2mg/day, but does not enhance efficacy of haloperidol, 2mg/day: comparison with reference dose risperidone, 6mg/day.Schizophr Res.2012 Nov;141(2-3):144-52.
18 Clinical pipeline report, company report or official report of Lundbeck.
19 Role of monoamine-oxidase-A-gene variation in the development of glioblastoma in males: a case control study. J Neurooncol. 2019 Nov;145(2):287-294.
20 Med-psych drug-drug interactions update. Psychosomatics. 2002 May;43(3):245-7.
21 Migraine pharmacotherapy with oral triptans: a rational approach to clinical management. Expert Opin Pharmacother. 2000 Mar;1(3):391-404.
22 Solid-phase synthesis and insights into structure-activity relationships of safinamide analogues as potent and selective inhibitors of type B monoamine oxidase. J Med Chem. 2007 Oct 4;50(20):4909-16.
23 Clinical pharmacokinetics of almotriptan, a serotonin 5-HT(1B/1D) receptor agonist for the treatment of migraine. Clin Pharmacokinet. 2005;44(3):237-46.
24 Metabolism of tresperimus by rat aorta semicarbazide-sensitive amine oxidase (SSAO). Fundam Clin Pharmacol. 2002 Dec;16(6):461-70.
25 Predictive toxicology using systemic biology and liver microfluidic "on chip" approaches: application to acetaminophen injury. Toxicol Appl Pharmacol. 2012 Mar 15;259(3):270-80.
26 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
27 Cardiovascular effects of rilmenidine, moxonidine and clonidine in conscious wild-type and D79N alpha2A-adrenoceptor transgenic mice. Br J Pharmacol. 1999 Mar;126(6):1522-30. doi: 10.1038/sj.bjp.0702429.
28 Development of a neural teratogenicity test based on human embryonic stem cells: response to retinoic acid exposure. Toxicol Sci. 2011 Dec;124(2):370-7.
29 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
30 Identification of transcriptome signatures and biomarkers specific for potential developmental toxicants inhibiting human neural crest cell migration. Arch Toxicol. 2016 Jan;90(1):159-80.
31 Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39.
32 Integrative "-Omics" analysis in primary human hepatocytes unravels persistent mechanisms of cyclosporine A-induced cholestasis. Chem Res Toxicol. 2016 Dec 19;29(12):2164-2174.
33 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
34 Platelet alpha 2-adrenoceptor modifications induced by long-term treatment with indapamide in essential hypertension. Am J Med. 1988 Jan 29;84(1B):31-5.
35 Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst. 2009 Mar 4;101(5):306-20.
36 Retinoic acid receptor alpha amplifications and retinoic acid sensitivity in breast cancers. Clin Breast Cancer. 2013 Oct;13(5):401-8.
37 Identification of mechanisms of action of bisphenol a-induced human preadipocyte differentiation by transcriptional profiling. Obesity (Silver Spring). 2014 Nov;22(11):2333-43.
38 Physiological and toxicological transcriptome changes in HepG2 cells exposed to copper. Physiol Genomics. 2009 Aug 7;38(3):386-401.
39 Genistein and bisphenol A exposure cause estrogen receptor 1 to bind thousands of sites in a cell type-specific manner. Genome Res. 2012 Nov;22(11):2153-62.
40 Unique transcriptome, pathways, and networks in the human endometrial fibroblast response to progesterone in endometriosis. Biol Reprod. 2011 Apr;84(4):801-15.
41 Definition of transcriptome-based indices for quantitative characterization of chemically disturbed stem cell development: introduction of the STOP-Toxukn and STOP-Toxukk tests. Arch Toxicol. 2017 Feb;91(2):839-864.
42 Functional characterization of N-octyl 4-methylamphetamine variants and related bivalent compounds at the dopamine and serotonin transporters using Ca(2+) channels as sensors. Toxicol Appl Pharmacol. 2021 May 15;419:115513. doi: 10.1016/j.taap.2021.115513. Epub 2021 Mar 27.
43 Dopamine transporter gene associated with diminished subjective response to amphetamine. Neuropsychopharmacology. 2005 Mar;30(3):602-9. doi: 10.1038/sj.npp.1300637.
44 Pharmacological Chaperones of the Dopamine Transporter Rescue Dopamine Transporter Deficiency Syndrome Mutations in Heterologous Cells. J Biol Chem. 2016 Oct 14;291(42):22053-22062. doi: 10.1074/jbc.M116.749119. Epub 2016 Aug 23.
45 Evaluation of first generation synthetic cannabinoids on binding at non-cannabinoid receptors and in a battery of in?vivo assays in mice. Neuropharmacology. 2016 Nov;110(Pt A):143-153. doi: 10.1016/j.neuropharm.2016.07.016. Epub 2016 Jul 20.
46 Effects of 1alpha,25 dihydroxyvitamin D3 and testosterone on miRNA and mRNA expression in LNCaP cells. Mol Cancer. 2011 May 18;10:58.
47 Pharmacological characterization of the aminorex analogs 4-MAR, 4,4'-DMAR, and 3,4-DMAR. Neurotoxicology. 2019 May;72:95-100. doi: 10.1016/j.neuro.2019.02.011. Epub 2019 Feb 15.
48 Pyrethroid pesticide-induced alterations in dopamine transporter function. Toxicol Appl Pharmacol. 2006 Mar 15;211(3):188-97. doi: 10.1016/j.taap.2005.06.003. Epub 2005 Jul 11.
49 Interindividual variability in 5-Fluorouracil metabolism and procainamide N-acetylation in human liver cytosol. Biol Pharm Bull. 2005 Jun;28(6):1071-4. doi: 10.1248/bpb.28.1071.
50 Eukaryotic arylamine N-acetyltransferase. Investigation of substrate specificity by high-throughput screening. Biochem Pharmacol. 2005 Jan 15;69(2):347-59. doi: 10.1016/j.bcp.2004.09.014. Epub 2004 Nov 24.
51 Association analysis of N-acetyl transferase-2 polymorphisms with aspirin intolerance among asthmatics. Pharmacogenomics. 2010 Jul;11(7):951-8. doi: 10.2217/pgs.10.65.
52 Analysis of nucleotide diversity of NAT2 coding region reveals homogeneity across Native American populations and high intra-population diversity. Pharmacogenomics J. 2007 Apr;7(2):144-52. doi: 10.1038/sj.tpj.6500407. Epub 2006 Jul 18.
53 The xenobiotic-metabolizing enzymes arylamine N-acetyltransferases in human lens epithelial cells: inactivation by cellular oxidants and UVB-induced oxidative stress. Mol Pharmacol. 2005 Apr;67(4):1299-306.
54 Simultaneous action of the flavonoid quercetin on cytochrome P450 (CYP) 1A2, CYP2A6, N-acetyltransferase and xanthine oxidase activity in healthy volunteers. Clin Exp Pharmacol Physiol. 2009 Aug;36(8):828-33.
55 Vitamin D3 transactivates the zinc and manganese transporter SLC30A10 via the Vitamin D receptor. J Steroid Biochem Mol Biol. 2016 Oct;163:77-87.
56 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
57 From transient transcriptome responses to disturbed neurodevelopment: role of histone acetylation and methylation as epigenetic switch between reversible and irreversible drug effects. Arch Toxicol. 2014 Jul;88(7):1451-68.