IMPPAT Phytochemical information: 
N,N-Dimethyltryptamine
N,N-Dimethyltryptamine
Summary

SMILES: CN(CCc1c[nH]c2c1cccc2)C
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
DeepSMILES: CNCCcc[nH]cc5cccc6)))))))))))C
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CN(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Tryptamines and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
n, n-dimethyltryptamine, n,n-dimethyltryptamine, n,n-dimethyl-tryptamine, dimethyltryptamine
External chemical identifiers:
CID:CID_6089; ChEMBL:CHEMBL12420; ChEBI:CHEBI:28969; ZINC:ZINC000000897457; FDASRS:WUB601BHAA; SureChEMBL:SCHEMBL335710
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
N,N-Dimethyltryptamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 188.27
Log P RDKit 2.27
Topological polar surface area (Å2) RDKit 19.03
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
N,N-Dimethyltryptamine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.78
N,N-Dimethyltryptamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.26
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
N,N-Dimethyltryptamine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000276198HTR2C778
ENSP00000277010SIGMAR1919
ENSP00000289753HTR6912
ENSP00000313661HTR1D936
ENSP00000316244HTR1A953
ENSP00000367959HTR2A961
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.