Dimethyltryptamine

Details

• Internal ID: 175cdd86-80af-41f2-b894-d8198d39252c
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives
• IUPAC Name: 2-(1H-indol-3-yl)-N,N-dimethylethanamine
• SMILES (Canonical): CN(C)CCC1=CNC2=CC=CC=C21
• SMILES (Isomeric): 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
• InChI Key: DMULVCHRPCFFGV-UHFFFAOYSA-N
• Popularity: 1,319 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆N₂
• Molecular Weight: 188.27 g/mol
• Exact Mass: 188.131348519 g/mol
• Topological Polar Surface Area (TPSA): 19.00 Ų
• XlogP: 2.50

Synonyms

• DIMETHYLTRYPTAMINE
• 61-50-7
• 2-(3-Indolyl)ethyldimethylamine
• 3-(2-Dimethylaminoethyl)indole
• 1H-Indole-3-ethanamine, N,N-dimethyl-
• 2-(1H-Indol-3-yl)-N,N-dimethylethanamine
• N,N-Dimethyl-1H-indole-3-ethylamine
• DMT (psychogenic)
• DMT
• N,N-dimethyl-1H-Indole-3-ethanamine
• DEA No. 7435
• UNII-WUB601BHAA
• 3-[2-(dimethylamino)ethyl]indole
• WUB601BHAA
• EINECS 200-508-4
• NSC 63795
• BRN 0138259
• CHEBI:28969
• HSDB 8017
• NSC-63795
• N-DIMETHYLTRYPTAMINE
• Indole, 3-(2-(dimethylamino)ethyl)-
• CHEMBL12420
• DTXSID60110053
• (2-Indol-3-ylethyl)dimethylamine
• Indole, 3-[2-(dimethylamino)ethyl]-
• [2-(1H-indol-3-yl)ethyl]dimethylamine
• 3-(2-(DIMETHYLAMINO)ETHYL)INDOLE
• [2-(1H-INDOL-3-YL)-ETHYL]-DIMETHYL-AMINE
• DIMETHYLTRYPTAMINE (MART.)
• DIMETHYLTRYPTAMINE [MART.]
• (psychogenic)
• N,N Dimethyltryptamine
• 2-(1H-INDOL-3-YL)-N,N-DIMETHYL-ETHANAMINE
• NN-Dimethyltryptamine
• Dimethyltryptamine(DMT)
• (N,N)-Dimethyltryptamine
• D0K1QS
• GTPL141
• 3-(dimethylaminoethyl)-indole
• SCHEMBL335710
• DTXCID4065313
• N,N-Dimethyltryptamine, free base
• DIMETHYLTRYPTAMINE [WHO-DD]
• N,N-DIMETHYLTRYPTAMINE [MI]
• NSC63795
• WLN: T56 BMJ D2N1&1
• 3-(2-(dimethylamino)ethyl)-Indole
• N,N-dimethyl-1H-indol-3-ethylamin
• BDBM50026868
• STK370594
• 3-[2- (dimethylamino)ethyl]-Indole
• AKOS005446117
• DB01488
• MB00483
• 3-(2-DIMETHYLAMINOETHYL) INDOLE
• 2-(1H-indol-3-yl)-ethyl-dimethyl-amine
• AS-47089
• LS-82930
• N,N-Dimethyltryptamine, >=97% (HPLC)
• 2-(1H-indol-3-yl)-N,N-dimethylethylamine
• 1H-INDOLE-3-ETHANAMINE,N,N-DIMETHYL
• N,N-dimethyl-1H-Indole-3-ethanamine (9CI)
• 2-(1H-Indol-3-yl)-N,N-dimethylethanamine #
• C08302
• D-5500
• L001288
• Q407217
• 2-(1H-indol-3-yl)-N,N-dimethylethanamine (ACD/Name 4.0)
• N-(2-(1H-indol-3-yl)ethyl)-N,N-dimethylamine (ACD/Name 4.0)
• InChI=1/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	410 nM	Ki	DOI: 10.1021/np960678l
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	65 nM	Ki	PMID: 10090793
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	101 nM	Ki	PMID: 10090793
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	33 nM	Ki	PMID: 10090793

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.92%	91.11%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	96.49%	90.71%
CHEMBL240	Q12809	HERG	95.62%	89.76%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.14%	93.99%
CHEMBL2581	P07339	Cathepsin D	94.89%	98.95%
CHEMBL3310	Q96DB2	Histone deacetylase 11	94.08%	88.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.68%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.81%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	91.07%	90.08%
CHEMBL1914	P06276	Butyrylcholinesterase	90.87%	95.00%
CHEMBL1937	Q92769	Histone deacetylase 2	87.62%	94.75%
CHEMBL228	P31645	Serotonin transporter	85.37%	95.51%
CHEMBL255	P29275	Adenosine A2b receptor	84.85%	98.59%
CHEMBL2996	Q05655	Protein kinase C delta	84.51%	97.79%
CHEMBL3401	O75469	Pregnane X receptor	83.92%	94.73%
CHEMBL2885	P07451	Carbonic anhydrase III	82.79%	87.45%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.93%	96.67%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.83%	85.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.34%	92.62%

Plants that contains it

• Acacia confusa
• Acacia maidenii
• Acacia phlebophylla
• Allium sativum
• Arisaema decipiens
• Arundo donax
• Catharanthus roseus
• Lespedeza bicolor
• Mimosa tenuiflora
• Phalaris aquatica
• Phyllodium pulchellum
• Pleurolobus gangeticus
• Stenostomum lucidum
• Vachellia rigidula
• Vepris ampody
• Virola sebifera
• Zanthoxylum arborescens

Cross-Links

• PubChem: 6089
• NPASS: NPC73767
• ChEMBL: CHEMBL12420
• LOTUS: LTS0223878
• wikiData: Q407217