Molecule

N,N-Dimethyltryptamine

AlkaPlorer ID: AK016972

Synonym: N,N-Dimethyl-1H-indole-3-ethanamine, 3-(2-Dimethylaminoethyl)indole, Nigerine, DMT

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

Structure

SMILES: CN(C)CCC1=CNC2=C1C=CC=C2

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

Reference

Catharanthus alkaloids—XXXIX

PubChem CID: 6089

CAS: 61-50-7

LOTUS: LTS0223878

NPASS: NPC73767

COCONUT: CNP0162089

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
None	Desmodium	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Arundo donax	Arundo	Poaceae	Poales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Zanthoxylum	Rutaceae	Sapindales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Homo sapiens	Homo	Hominidae	Primates	Mammalia	Chordata	Metazoa	Eukaryota
None	Acacia	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Phalaris	Poaceae	Poales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Allium sativum	Allium	Amaryllidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Mucuna pruriens	Mucuna	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Banisteriopsis	Malpighiaceae	Malpighiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Mimosa	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Psychotria	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Virola	Myristicaceae	Magnoliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	None	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	None	Myristicaceae	Magnoliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Zanthoxylum	Rutaceae	Sapindales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 188.274

TPSA？: 19.03

MolLogP？: 2.272

Number of H-Donors: 1

Number of H-Acceptors: 1

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Cavia porcellus	Sigma-1 receptor	Ki	15000.0	nM	10.1016/j.bmc.2011.04.002
Hepatitis B virus	Hepatitis B virus	IC50	100000.0	nM	10.1016/j.bmc.2011.04.004
Homo sapiens	Serotonin 1a (5-HT1a) receptor	Ki	410.0	nM	10.1021/np960678l
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	22.2	nM	10.1021/acsmedchemlett.1c00577
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	22.2	nM	10.1021/acsmedchemlett.2c00129
Homo sapiens	Serotonin 2a (5-HT2a) receptor	Emax	93.4	%	10.1021/acsmedchemlett.1c00577
Homo sapiens	Serotonin 2a (5-HT2a) receptor	Ki	65.0	nM	10.1021/jm980692q
Homo sapiens	Serotonin 2b (5-HT2b) receptor	Ki	101.0	nM	10.1021/jm980692q
Homo sapiens	Serotonin 2c (5-HT2c) receptor	Ki	33.0	nM	10.1021/jm980692q
Homo sapiens	Whole blood	Retention_time	2.89	min	10.1007/s00044-012-9977-1
Mus musculus	Mus musculus	ED50	5.05	umol.kg-1	10.1021/acs.jnatprod.1c00087
Rattus norvegicus	Cortical neurone	Activity	nan	None	10.1021/acs.jmedchem.9b01404
Rattus norvegicus	GABA-A receptor; anion channel	Ki	100000.0	nM	10.1021/jm00351a015
Rattus norvegicus	Rattus norvegicus	D	0.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	D	11.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	D	18.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	D	20.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	D	23.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	D	37.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	D	80.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	Kd	1000.0	nM	10.1021/jm00353a021
Rattus norvegicus	Rattus norvegicus	SDL	0.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	SDL	20.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	SDL	22.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	SDL	37.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	SDL	37.5	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	SDL	40.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	SDL	62.5	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	SDL	83.0	%	10.1021/jm980692q
Rattus norvegicus	Rattus norvegicus	SDL	100.0	%	10.1021/jm980692q
Rattus norvegicus	Serotonin 1 (5-HT1) receptor	Kd	1000.0	nM	10.1021/jm00197a025
Rattus norvegicus	Serotonin 1a (5-HT1a) receptor	Ki	259.0	nM	10.1021/jm980692q
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	ED50	3.24	mg.kg-1	10.1021/jm980692q
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	ED50	10.6	umol.kg-1	10.1021/jm980692q
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	Efficacy	nan	None	10.1016/j.bmc.2008.02.033
Rattus norvegicus	Serotonin 2a (5-HT2a) receptor	Ki	1636.0	nM	10.1016/j.bmc.2008.02.033
Rattus norvegicus	Serotonin 2b (5-HT2b) receptor	Kd	1000.0	nM	10.1021/jm00343a013
Rattus norvegicus	Serotonin (5-HT) receptor	Kd	1000.0	nM	10.1021/jm00185a014
Rattus norvegicus	Serotonin (5-HT) receptor	Kd	1000.0	nM	10.1021/jm00206a022
Rattus norvegicus	Sigma opioid receptor	Ki	15400.0	nM	10.1021/jm400660u
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	IC50	19952.62	nM	10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	IC50	20000.0	nM	10.6019/CHEMBL4651402
None	ADMET	CC50	100000.0	nM	10.1016/j.bmc.2011.04.004
None	ADMET	CL	134.9	mL.min-1.g-1	10.1021/acsmedchemlett.2c00129
None	ADMET	CLH	19.4	uL/min	10.1021/acsmedchemlett.2c00354
None	ADMET	Stability	0.0	%	10.1021/acsmedchemlett.2c00129
None	ADMET	Stability	8.9	%	10.1021/acsmedchemlett.2c00129
None	ADMET	T1/2	0.085	hr	10.1021/acsmedchemlett.2c00129
None	ADMET	T1/2	0.285	hr	10.1021/acsmedchemlett.2c00129
None	ADMET	T1/2	1.648	hr	10.1021/acsmedchemlett.2c00354
None	No relevant target	LogP	0.262	None	10.1016/j.bmc.2008.02.033
None	No relevant target	LogP	2.61	None	10.1021/jm00197a025
None	Unchecked	Ratio CC50/IC50	nan	None	10.1016/j.bmc.2011.04.004

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT014563	C[SAH].CNCCc1c[nH]c2ccccc12>>CN(C)CCc1c[nH]c2ccccc12	enzymemap_27462