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
CHEBI:64629
CAS Number
64584-34-5
TTD ID
D07XTU

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]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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.