Details of the Drug

General Information of Drug (ID: DMG0EL7)

Drug Name

5-MEO-DMT

Synonyms

N,N-Dimethyl-5-methoxytryptamine; 5-Methoxy-N,N-dimethyltryptamine; 1019-45-0; Methoxybufotenin; O-Methylbufotenine; Methylbufotenine; MeODMT; 5-MeO-DMT; 5-Methoxydimethyltryptamine; Bufotenine, O-methyl-; 3-(2-Dimethylaminoethyl)-5-methoxyindole; 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine; CT 4334; Methoxydimethyltryptamines; UNII-X0MKX3GWU9; 1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl-; NSC 88624; 5-Methoxy-N,N-dimethyl-1H-indole-3-ethanamine; 5-OMe-DMT; INDOLE, 3-(2-(N,N-DIMETHYLAMINO)ETHYL)-5-METHOXY-

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)

218.29

Logarithm of the Partition Coefficient (xlogp)

1.5

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

2

Chemical Identifiers

Formula: C13H18N2O
IUPAC Name: 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
Canonical SMILES: CN(C)CCC1=CNC2=C1C=C(C=C2)OC
InChI: InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
InChIKey: ZSTKHSQDNIGFLM-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 1832
ChEBI ID: CHEBI:2086
CAS Number: 1019-45-0
UNII: X0MKX3GWU9
DrugBank ID: DB14010
TTD ID: D0C5XQ
INTEDE ID: DR0021

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 2B receptor (HTR2B)	TT0K1SC	5HT2B_HUMAN	Inhibitor	[2]
5-HT 2C receptor (HTR2C)	TTWJBZ5	5HT2C_HUMAN	Inhibitor	[2]
5-HT 6 receptor (HTR6)	TTJS8PY	5HT6R_HUMAN	Inhibitor	[3]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[5]
Cytochrome P450 2B6 (CYP2B6)	OTOYO4S7	CP2B6_HUMAN	Gene/Protein Processing	[5]
Cytochrome P450 2D6 (CYP2D6)	OTZJC802	CP2D6_HUMAN	Gene/Protein Processing	[5]
Cytochrome P450 2E1 (CYP2E1)	OTHQ17JG	CP2E1_HUMAN	Gene/Protein Processing	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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
Cytochrome P450 2D6 (CYP2D6)	DME	CYP2D6	7.30E-01	-1.91E-02	-1.41E-01

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

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: 145).
2	1-((S)-2-aminopropyl)-1H-indazol-6-ol: a potent peripherally acting 5-HT2 receptor agonist with ocular hypotensive activity. J Med Chem. 2006 Jan 12;49(1):318-28.
3	Interaction of N1-unsubstituted and N1-benzenesulfonyltryptamines at h5-HT6 receptors. Bioorg Med Chem Lett. 2006 Nov 15;16(22):5832-5.
4	Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions. Curr Drug Metab. 2010 Oct;11(8):659-66.
5	Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol Lett. 2016 Jan 22;241:82-94.