Details of the Drug

General Information of Drug (ID: DMR9Q4Y)

Drug Name

2-(1H-indol-3-yl)-N,N-dimethylethanamine

Synonyms

N,N-Dimethyltryptamine; N,N-DIMETHYLTRYPTAMINE; DIMETHYLTRYPTAMINE; 61-50-7; 3-(2-Dimethylaminoethyl)indole; 2-(3-Indolyl)ethyldimethylamine; N,N-Dimethyl-1H-indole-3-ethylamine; 2-(1H-Indol-3-yl)-N,N-dimethylethanamine; 1H-Indole-3-ethanamine, N,N-dimethyl-; DMT (psychogenic); (psychogenic); UNII-WUB601BHAA; 3-[2-(dimethylamino)ethyl]indole; EINECS 200-508-4; NSC 63795; WUB601BHAA; N,N-dimethyl-1H-Indole-3-ethanamine; BRN 0138259; CHEMBL12420; DEA No 7435; CHEBI:28969; DMULVCHRPCFFGV-UHFFFAOYSA-N; (2-Indol-3-ylethyl)dimethylamine; Indole,; Dimethyltryptamine

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

188.27

Logarithm of the Partition Coefficient (xlogp)

2.5

Rotatable Bond Count (rotbonds)

3

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

1

Chemical Identifiers

Formula: C12H16N2
IUPAC Name: 2-(1H-indol-3-yl)-N,N-dimethylethanamine
Canonical SMILES: CN(C)CCC1=CNC2=CC=CC=C21
InChI: InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3
InChIKey: DMULVCHRPCFFGV-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 6089
ChEBI ID: CHEBI:28969
CAS Number: 61-50-7
DrugBank ID: DB01488
TTD ID: D03DLZ

Combinatorial Drugs (CBD)

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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 6 receptor (HTR6)	TTJS8PY	5HT6R_HUMAN	Inhibitor	[2]
Opioid receptor sigma 1 (OPRS1)	TT5TPI6	SGMR1_HUMAN	Inhibitor	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
5-hydroxytryptamine receptor 2A (HTR2A)	OTWXJX0M	5HT2A_HUMAN	Drug Response	[3]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Regulation of Drug Effects	[4]
Cytochrome P450 2C19 (CYP2C19)	OTFMJYYE	CP2CJ_HUMAN	Regulation of Drug Effects	[4]
Flavin-containing monooxygenase 3 (FMO3)	OT1G2EV3	FMO3_HUMAN	Regulation of Drug Effects	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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 6 receptor (HTR6)	DTT	HTR6	1.23E-05	-0.12	-0.71
Opioid receptor sigma 1 (OPRS1)	DTT	SIGMAR1	2.77E-06	-0.12	-0.62

Molecular Expression Atlas (MEA)

MEA Detail

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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: 141).
2	Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects. Arch Gen Psychiatry. 1994 Feb;51(2):85-97.
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	What is the contribution of human FMO3 in the N-oxygenation of selected therapeutic drugs and drugs of abuse?. Toxicol Lett. 2016 Sep 6;258:55-70. doi: 10.1016/j.toxlet.2016.06.013. Epub 2016 Jun 15.