Details of the Drug

General Information of Drug (ID: DMAFPHB)

Drug Name
TRYPTAMINE
Synonyms
tryptamine; 61-54-1; 2-(1H-Indol-3-yl)ethanamine; 3-(2-aminoethyl)indole; 1H-Indole-3-ethanamine; 2-(3-Indolyl)ethylamine; Indol-3-ethylamine; Indole, 3-(2-aminoethyl)-; 2-(Indol-3-yl)ethylamine; 2-(1H-Indol-3-Yl)Ethan-1-Amine; 3-Indoleethylamine; Tryptamin; 2-(1H-indol-3-yl)ethylamine; 2-Indol-3-ylethylamine; 2-(1H-INDOL-3-YL)-ETHYLAMINE; UNII-422ZU9N5TV; (Amino-2 ethyl)-3 indole; (Amino-2 ethyl)-3 indole [French]; Tryptamine, 98%; BRN 0125513; EINECS 200-510-5; CHEMBL6640; 422ZU9N5TV; CHEBI:16765; APJYDQYYACXCRM-UHFFFAOYSA-N
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 160.22
Logarithm of the Partition Coefficient (xlogp) 1.6
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 1
Chemical Identifiers
Formula
C10H12N2
IUPAC Name
2-(1H-indol-3-yl)ethanamine
Canonical SMILES
C1=CC=C2C(=C1)C(=CN2)CCN
InChI
InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
InChIKey
APJYDQYYACXCRM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
1150
ChEBI ID
CHEBI:16765
CAS Number
61-54-1
DrugBank ID
DB08653
TTD ID
D08CJK

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 [1]
Monoamine oxidase type A (MAO-A) TT3WG5C AOFA_HUMAN Inhibitor [2]
Monoamine oxidase type B (MAO-B) TTGP7BY AOFB_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5-hydroxytryptamine receptor 2A (HTR2A) OTWXJX0M 5HT2A_HUMAN Drug Response [3]
Amine oxidase A (MAOA) OT8NIWMQ AOFA_HUMAN Biotransformations [4]
Amine oxidase B (MAOB) OTTDFM1O AOFB_HUMAN Biotransformations [4]
Cytochrome P450 2A6 (CYP2A6) OT52TWG3 CP2A6_HUMAN Gene/Protein Processing [5]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [6]
Trace amine-associated receptor 1 (TAAR1) OTUY8CGM TAAR1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
5-HT 2A receptor (HTR2A) DTT HTR2A 4.32E-01 0.15 0.13
Monoamine oxidase type B (MAO-B) DTT MAOB 3.49E-01 -0.02 -0.19
Monoamine oxidase type A (MAO-A) DTT MAOA 4.12E-01 -0.02 -0.08
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Central serotonin receptors as targets for drug research. J Med Chem. 1987 Jan;30(1):1-12.
2 Binding of beta-carbolines at imidazoline I2 receptors: a structure-affinity investigation. Bioorg Med Chem Lett. 2004 Feb 23;14(4):999-1002.
3 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.
4 Evidence for new light-independent pathways for generation of the endogenous aryl hydrocarbon receptor agonist FICZ. Chem Res Toxicol. 2016 Jan 19;29(1):75-86.
5 Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro. Drug Metab Dispos. 2001 Jun;29(6):897-902.
6 Indole microbial intestinal metabolites expand the repertoire of ligands and agonists of the human pregnane X receptor. Toxicol Lett. 2020 Nov 1;334:87-93. doi: 10.1016/j.toxlet.2020.09.015. Epub 2020 Sep 28.
7 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.