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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine
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Accession:CHEBI:64629 term browser browse the term
Definition:An organoiodine compound that is amphetamine bearing two methoxy substituents at positions 2 and 5 as well as an iodo substituent at position 4.
Synonyms:exact_synonym: 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine
 related_synonym: 1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane;   1-(4-Iodo-2,5-dimethoxyphenyl)-2-aminopropane;   2,5-Dimethoxy-4-iodoamphetamine;   2,5-Dimethoxy-4-iodophenylisopropylamine;   4-DOI;   4-Iodo-2,5-dimethoxyphenylisopropylamine;   Formula=C11H16INO2;   InChI=1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3;   InChIKey=BGMZUEKZENQUJY-UHFFFAOYSA-N;   SMILES=COc1cc(CC(C)N)c(OC)cc1I
 xref: CAS:64584-34-5
 xref_mesh: MESH:C015952
 xref: Reaxys:2727017


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2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A increases activity ISO 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of ABCB1 protein CTD PMID:23273999 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Abcg2 ATP binding cassette subfamily G member 2 increases activity ISO 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of ABCG2 protein CTD PMID:30083819 NCBI chr 4:87,676,241...87,802,757
Ensembl chr 4:87,745,319...87,802,409 		JBrowse link
G Adcyap1 adenylate cyclase activating polypeptide 1 multiple interactions
increases response to substance		 ISO ADCYAP1 gene mutant form promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of FOS protein]
ADCYAP1 gene mutant form results in increased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine		 CTD PMID:24586556 NCBI chr 9:113,102,632...113,122,500
Ensembl chr 9:113,103,718...113,109,773 		JBrowse link
G Aifm1 apoptosis inducing factor, mitochondria associated 1 increases expression EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of AIFM1 protein CTD PMID:22983118 NCBI chr  X:127,650,223...127,689,356
Ensembl chr  X:127,650,226...127,689,256 		JBrowse link
G Bdnf brain-derived neurotrophic factor multiple interactions
increases expression		 ISO [Poly I-C results in increased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine] which results in increased expression of BDNF mRNA; Poly I-C promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of BDNF mRNA] CTD PMID:24889602 NCBI chr 3:96,165,042...96,215,621
Ensembl chr 3:96,165,042...96,215,615 		JBrowse link
G Casp3 caspase 3 increases activity EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of CASP3 protein CTD PMID:22983118 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp8 caspase 8 increases activity EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of CASP8 protein CTD PMID:22983118 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542 		JBrowse link
G Cycs cytochrome c, somatic affects localization EXP 4-iodo-2,5-dimethoxyphenylisopropylamine affects the localization of CYCS protein CTD PMID:22983118 NCBI chr 4:79,651,894...79,653,994
Ensembl chr 4:79,651,378...79,654,054
Ensembl chr18:79,651,378...79,654,054 		JBrowse link
G Egr1 early growth response 1 increases expression
multiple interactions		 ISO 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of EGR1 mRNA
[Poly I-C results in increased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine] which results in increased expression of EGR1 mRNA; Poly I-C promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of EGR1 mRNA]		 CTD PMID:24889602 NCBI chr18:26,462,967...26,466,766
Ensembl chr18:26,462,981...26,466,766 		JBrowse link
G Egr2 early growth response 2 increases expression
multiple interactions		 ISO 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of EGR2 protein
Risperidone inhibits the reaction [Toluene promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of EGR2 protein]]; Toluene promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of EGR2 protein]		 CTD PMID:32980479 NCBI chr20:21,051,270...21,056,322
Ensembl chr20:21,051,277...21,055,562 		JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit increases expression
multiple interactions		 EXP
ISO		 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of FOS protein
ADCYAP1 gene mutant form promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of FOS protein]; Risperidone inhibits the reaction [Toluene promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of FOS protein]]; Toluene promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of FOS protein]		 CTD PMID:12482207 PMID:24586556 PMID:32980479 NCBI chr 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036 		JBrowse link
G Gnai1 G protein subunit alpha i1 increases activity
multiple interactions		 ISO 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of GNAI1 protein
Dronabinol promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of GNAI1 protein]; Sirolimus inhibits the reaction [Dronabinol promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of GNAI1 protein]]		 CTD PMID:29748632 NCBI chr 4:16,814,000...16,898,119
Ensembl chr 4:16,814,001...16,896,417 		JBrowse link
G Gnai3 G protein subunit alpha i3 increases activity
multiple interactions		 ISO 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of GNAI3 protein
Dronabinol promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of GNAI3 protein]; Sirolimus inhibits the reaction [Dronabinol promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of GNAI3 protein]]		 CTD PMID:29748632 NCBI chr 2:195,742,765...195,780,720
Ensembl chr 2:195,742,642...195,780,742 		JBrowse link
G Gnao1 G protein subunit alpha o1 multiple interactions ISO [Dronabinol results in increased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine] which results in increased activity of GNAO1 protein CTD PMID:29748632 NCBI chr19:11,034,874...11,192,531
Ensembl chr19:11,035,956...11,192,493 		JBrowse link
G Gnaz G protein subunit alpha z increases activity
multiple interactions		 ISO 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of GNAZ protein
Dronabinol promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of GNAZ protein]; Sirolimus inhibits the reaction [Dronabinol promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of GNAZ protein]]		 CTD PMID:29748632 NCBI chr20:13,643,473...13,694,240
Ensembl chr20:13,644,640...13,669,907 		JBrowse link
G Htr2a 5-hydroxytryptamine receptor 2A multiple interactions
increases response to substance
decreases response to substance
affects response to substance
increases activity
affects binding		 ISO
EXP		 4-iodo-2,5-dimethoxyphenylisopropylamine inhibits the reaction [Ketanserin binds to HTR2A protein]; [Alprenolol co-treated with Cocaine] affects the reaction [HTR2A protein results in increased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine]; [Yohimbine co-treated with Cocaine] affects the reaction [HTR2A protein results in increased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine]; Cocaine inhibits the reaction [HTR2A protein results in increased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine]
1-(8-bromobenzo(1,2-b;4,5-b')difuran-4-yl)-2-aminopropane inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine binds to HTR2A protein]; 4-iodo-2,5-dimethoxyphenylisopropylamine binds to and results in increased activity of HTR2A protein
HTR2A gene SNP results in decreased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine
HTR2A protein affects the susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine
4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of HTR2A protein
4-iodo-2,5-dimethoxyphenylisopropylamine binds to and results in increased activity of HTR2A protein; [4-iodo-2,5-dimethoxyphenylisopropylamine binds to and results in increased activity of HTR2A protein] which results in increased secretion of and results in increased abundance of Dopamine; Cocaine promotes the reaction [[4-iodo-2,5-dimethoxyphenylisopropylamine binds to and results in increased activity of HTR2A protein] which results in increased secretion of and results in increased abundance of Dopamine]; Ketanserin inhibits the reaction [[4-iodo-2,5-dimethoxyphenylisopropylamine binds to and results in increased activity of HTR2A protein] which results in increased secretion of and results in increased abundance of Dopamine]; Ketanserin inhibits the reaction [Cocaine promotes the reaction [[4-iodo-2,5-dimethoxyphenylisopropylamine binds to and results in increased activity of HTR2A protein] which results in increased secretion of and results in increased abundance of Dopamine]]; Streptozocin inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased activity of HTR2A protein]		 CTD PMID:8392199 PMID:9857084 PMID:10773215 PMID:12482207 PMID:16314884 More... NCBI chr15:49,950,035...50,022,188
Ensembl chr15:49,950,804...50,020,928 		JBrowse link
G Htr2c 5-hydroxytryptamine receptor 2C multiple interactions
affects binding		 ISO 1-(8-bromobenzo(1,2-b;4,5-b')difuran-4-yl)-2-aminopropane inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine binds to HTR2C protein] CTD PMID:9857084 NCBI chr  X:110,640,777...110,870,288
Ensembl chr  X:110,641,153...110,870,287 		JBrowse link
G Il1b interleukin 1 beta increases expression
multiple interactions		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of IL1B protein
4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of and results in increased secretion of IL1B protein; gastrodin inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of IL1B protein]; rhyncophylline inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of and results in increased secretion of IL1B protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of and results in increased secretion of IL1B protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of IL1B protein]		 CTD PMID:30790395 PMID:31231976 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il6 interleukin 6 increases expression
multiple interactions		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of IL6 protein
4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of and results in increased secretion of IL6 protein; gastrodin inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of IL6 protein]; rhyncophylline inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of and results in increased secretion of IL6 protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of and results in increased secretion of IL6 protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of IL6 protein]		 CTD PMID:30790395 PMID:31231976 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Jak2 Janus kinase 2 increases phosphorylation
multiple interactions		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of JAK2 protein
rhyncophylline inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of JAK2 protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of JAK2 protein]		 CTD PMID:31231976 NCBI chr 1:226,995,334...227,054,381
Ensembl chr 1:226,995,334...227,054,189 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation
multiple interactions		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of MAPK1 protein
Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of MAPK1 protein]		 CTD PMID:30790395 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation
multiple interactions		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of MAPK3 protein
Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of MAPK3 protein]		 CTD PMID:30790395 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 increases phosphorylation
multiple interactions		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of MAPK8 protein
gastrodin inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of MAPK8 protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of MAPK8 protein]		 CTD PMID:30790395 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Myd88 MYD88, innate immune signal transduction adaptor multiple interactions
increases expression		 EXP gastrodin inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of MYD88 protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of MYD88 protein] CTD PMID:30790395 NCBI chr 8:119,074,439...119,078,508
Ensembl chr 8:119,074,437...119,079,415 		JBrowse link
G Nfkbia NFKB inhibitor alpha increases phosphorylation
multiple interactions		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of NFKBIA protein
rhyncophylline inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of NFKBIA protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of NFKBIA protein]		 CTD PMID:31231976 NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941 		JBrowse link
G Nos1 nitric oxide synthase 1 increases expression EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of NOS1 protein CTD PMID:12482207 NCBI chr12:38,615,111...38,795,492
Ensembl chr12:38,626,714...38,710,945 		JBrowse link
G Pdyn prodynorphin decreases expression EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in decreased expression of PDYN mRNA CTD PMID:9526047 NCBI chr 3:116,900,990...116,913,334
Ensembl chr 3:116,900,992...116,913,334 		JBrowse link
G Ppp1r1b protein phosphatase 1, regulatory (inhibitor) subunit 1B increases phosphorylation ISO 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of PPP1R1B protein CTD PMID:11880652 NCBI chr10:83,347,731...83,356,775
Ensembl chr10:83,347,731...83,356,775 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 increases expression
multiple interactions		 ISO 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of PTGS2 mRNA
[Poly I-C results in increased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine] which results in increased expression of PTGS2 mRNA; Poly I-C promotes the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of PTGS2 mRNA]		 CTD PMID:24889602 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit increases phosphorylation
multiple interactions		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of RELA protein
gastrodin inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of RELA protein]; rhyncophylline inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of RELA protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of RELA protein]		 CTD PMID:30790395 PMID:31231976 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions
increases phosphorylation		 EXP rhyncophylline inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of STAT3 protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased phosphorylation of STAT3 protein] CTD PMID:31231976 NCBI chr10:85,811,206...85,863,057
Ensembl chr10:85,811,218...85,863,057 		JBrowse link
G Tlr4 toll-like receptor 4 increases expression
multiple interactions		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of TLR4 protein
gastrodin inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of TLR4 protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of TLR4 protein]		 CTD PMID:30790395 NCBI chr 5:80,145,867...80,159,501
Ensembl chr 5:80,145,826...80,159,628 		JBrowse link
G Tnf tumor necrosis factor multiple interactions
increases expression		 EXP 4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of and results in increased secretion of TNF protein; gastrodin inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of TNF protein]; rhyncophylline inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of and results in increased secretion of TNF protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of and results in increased secretion of TNF protein]; Tiapride Hydrochloride inhibits the reaction [4-iodo-2,5-dimethoxyphenylisopropylamine results in increased expression of TNF protein] CTD PMID:30790395 PMID:31231976 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 19811
    role 19818
      biological role 19785
        xenobiotic 18731
          amphetamine 2214
            2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine 33
Path 2
Term Annotations click to browse term
  CHEBI ontology 19811
    subatomic particle 19809
      composite particle 19809
        hadron 19840
          baryon 19809
            nucleon 19809
              atomic nucleus 19809
                atom 19809
                  main group element atom 19759
                    main group molecular entity 19759
                      s-block molecular entity 19628
                        hydrogen molecular entity 19614
                          hydrides 19087
                            inorganic hydride 18091
                              pnictogen hydride 18080
                                nitrogen hydride 17987
                                  azane 17796
                                    ammonia 17795
                                      organic amino compound 17795
                                        amine 8267
                                          primary amine 6317
                                            1-phenylpropan-2-amine 3595
                                              (R)-amphetamine 2214
                                                amphetamine 2214
                                                  2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine 33
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