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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 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
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 4:88,765,441...88,890,268
Ensembl chr 4:88,832,178...88,890,621
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 9:121,705,897...121,725,736
Ensembl chr 9:121,706,979...121,725,716
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:135,304,063...135,343,062
Ensembl chr  X:135,304,066...135,343,087
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 3:100,768,637...100,819,216
Ensembl chr 3:100,768,637...100,819,210
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 chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
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 4:80,331,226...80,333,326
Ensembl chr 4:80,331,227...80,333,326
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 chr18:27,657,903...27,660,101
Ensembl chr18:27,657,628...27,661,429
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]
CTD PMID:12482207 PMID:24586556 NCBI chr 6:109,300,433...109,303,299
Ensembl chr 6:109,300,433...109,303,299
JBrowse link
G Htr2a 5-hydroxytryptamine receptor 2A multiple interactions
affects binding
affects response to substance
increases response to substance
decreases response to substance
increases activity
ISO
EXP
[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]
4-iodo-2,5-dimethoxyphenylisopropylamine binds to HTR2A protein
HTR2A protein affects the susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine
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]
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
CTD PMID:8392199 PMID:9857084 PMID:10773215 PMID:12482207 PMID:16314884 PMID:18622176 PMID:22983118 NCBI chr15:56,666,152...56,732,469
Ensembl chr15:56,666,012...56,735,382
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:118,084,520...118,318,040
Ensembl chr  X:118,084,890...118,318,039
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 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
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 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
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 1:247,398,667...247,457,521
Ensembl chr 1:247,398,598...247,458,509
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 chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
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 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
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 chr16:9,620,854...9,709,342
Ensembl chr16:9,625,177...9,709,347
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 8:128,022,512...128,027,462
Ensembl chr 8:128,022,473...128,026,841
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 6:76,267,227...76,270,457
Ensembl chr 6:76,267,228...76,270,457
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 chr12:44,214,949...44,405,530
Ensembl chr12:44,213,943...44,520,341
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 3:122,194,327...122,206,671
Ensembl chr 3:122,194,329...122,206,671
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 chr10:86,303,727...86,312,770
Ensembl chr10:86,303,727...86,312,762
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 chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
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 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
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 chr10:88,790,401...88,842,263
Ensembl chr10:88,790,408...88,842,233
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 5:82,587,424...82,601,056
Ensembl chr 5:82,587,420...82,601,052
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 chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19841
    role 19792
      biological role 19792
        xenobiotic 18434
          amphetamine 2210
            2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine 28
Path 2
Term Annotations click to browse term
  CHEBI ontology 19841
    subatomic particle 19839
      composite particle 19839
        hadron 19839
          baryon 19839
            nucleon 19839
              atomic nucleus 19839
                atom 19839
                  main group element atom 19732
                    main group molecular entity 19732
                      s-block molecular entity 19481
                        hydrogen molecular entity 19473
                          hydrides 18745
                            inorganic hydride 17483
                              pnictogen hydride 17456
                                nitrogen hydride 17300
                                  azane 17016
                                    ammonia 17015
                                      organic amino compound 17014
                                        amine 7783
                                          primary amine 5682
                                            1-phenylpropan-2-amine 3481
                                              (R)-amphetamine 2210
                                                amphetamine 2210
                                                  2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine 28
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