Details of the Drug

General Information of Drug (ID: DM39FSQ)

Drug Name
Racemic DOI
Synonyms
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine; 4-DOI; 64584-34-5; 2,5-Dimethoxy-4-iodoamphetamine; DOI-P; 2,5-Dimethoxy-4-iodophenylisopropylamine; 1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane; 1-(4-Iodo-2,5-dimethoxyphenyl)-2-aminopropane; 4-Iodo-2,5-dimethoxyamphetamine; C11H16INO2; 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine; CHEMBL6616; CHEBI:64629; 4-Iodo-2,5-dimethoxy-alpha-methylbenzeneethanamine; Benzeneethanamine, 4-iodo-2,5-dimethoxy-alpha-methyl-; 82830-53-3
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 321.15
Logarithm of the Partition Coefficient (xlogp) 2.5
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C11H16INO2
IUPAC Name
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine
Canonical SMILES
CC(CC1=CC(=C(C=C1OC)I)OC)N
InChI
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
Cross-matching ID
PubChem CID
1229
ChEBI ID
CHEMBL64629
CAS Number
64584-34-5
TTD ID
D07XTU
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 2A receptor (HTR2A) TTJQOD7 5HT2A_HUMAN Inhibitor [2]
5-HT 2B receptor (HTR2B) TT0K1SC 5HT2B_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5-hydroxytryptamine receptor 2A (HTR2A) OTWXJX0M 5HT2A_HUMAN Drug Response [4]
5-hydroxytryptamine receptor 2C (HTR2C) OT6H8DE0 5HT2C_HUMAN Protein Interaction/Cellular Processes [5]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [6]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [7]
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Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
5-HT 2A receptor (HTR2A) DTT HTR2A 1.68E-01 -0.3 -0.14
5-HT 2A receptor (HTR2A) DTT HTR2A 5.59E-01 0.15 0.21
5-HT 2B receptor (HTR2B) DTT HTR2B 1.29E-01 -0.04 -0.14
5-HT 2B receptor (HTR2B) DTT HTR2B 1.13E-01 -0.04 -0.26
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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: 157).
2 The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg Med Chem. 2008 Apr 15;16(8):4661-9.
3 cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11,11a-octahydrobenzofuro[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist that blocks pain... J Med Chem. 2008 Nov 27;51(22):7094-8.
4 Pharmacologic analysis of non-synonymous coding h5-HT2A SNPs reveals alterations in atypical antipsychotic and agonist efficacies. Pharmacogenomics J. 2006 Jan-Feb;6(1):42-51. doi: 10.1038/sj.tpj.6500342.
5 A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor. J Med Chem. 1998 Dec 17;41(26):5148-9. doi: 10.1021/jm9803525.
6 Michaelis-Menten kinetic analysis of drugs of abuse to estimate their affinity to human P-glycoprotein. Toxicol Lett. 2013 Feb 27;217(2):137-42. doi: 10.1016/j.toxlet.2012.12.012. Epub 2012 Dec 27.
7 Inhibition and stimulation of the human breast cancer resistance protein as in vitro predictor of drug-drug interactions of drugs of abuse. Arch Toxicol. 2018 Sep;92(9):2875-2884. doi: 10.1007/s00204-018-2276-y. Epub 2018 Aug 6.