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
• #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
  UNII: 422ZU9N5TV
  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 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

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.