[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-dimethyl-amine

ID: ALA7257

Cas Number: 1019-45-0

PubChem CID: 1832

Product Number: M102782, Order Now?

Max Phase: Phase

Molecular Formula: C13H18N2O

Molecular Weight: 218.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 5-meo-dmt | 5-methoxy-n-dimethyltryptamine | 5-methoxydimethyltryptamine | Mebufotenin | NSC-88624 | N,N-Dimethyl-5-methoxytryptamine|1019-45-0|5-Methoxy-N,N-dimethyltryptamine|Methoxybufotenin|O-Methylbufotenine|5-MeO-DMT|5-Methoxydimethyltryptamine|MeODMT|Methylbufotenine|3-(2-Dimethylaminoethyl)-5-methoxyindole|Bufotenine, O-methyl-|2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine|1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl-|Mebufotenin|CT 4334|5-Methoxy-N,N-dimethyl-1H-indole-3-ethanamiShow More⌵

Synonyms from Alternative Forms(1): 5-Methoxy DMT oxalate

Canonical SMILES:  COc1ccc2[nH]cc(CCN(C)C)c2c1

Standard 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

Standard InChI Key:  ZSTKHSQDNIGFLM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
   -1.7993    1.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5138    1.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5138    0.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7993   -0.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0849    0.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0849    1.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6278    2.3026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074    2.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718    1.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7993   -0.9794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5138   -1.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3352    1.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872    2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6942    1.9053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2462    2.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491    1.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  7  8  1  0
  8  9  2  0
  1  7  1  0
  6  9  1  0
  4 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA7257

   MEBUFOTENIN

2. Alternative Forms:

   

   ALA7257

   5-Methoxy DMT oxalate

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 218.30

Molecular Weight (Monoisotopic): 218.1419

AlogP: 2.28

#Rotatable Bonds: 4

Polar Surface Area: 28.26

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.58

CX LogP: 2.14

CX LogD: -0.02

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.85

Np Likeness Score: -0.33

References

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13. Macor JE, Blake J, Fox CB, Johnson C, Koe BK, Lebel LA, Morrone JM, Ryan K, Schmidt AW, Schulz DW..  (1992)  Synthesis and serotonergic pharmacology of the enantiomers of 3-[(N-methylpyrrolidin-2-yl)methyl]-5-methoxy-1H-indole: discovery of stereogenic differentiation in the aminoethyl side chain of the neurotransmitter serotonin.,  35  (23): [PMID:1447752] [10.1021/jm00101a032]

14. Vermeulen ES, Schmidt AW, Sprouse JS, Wikström HV, Grol CJ..  (2003)  Characterization of the 5-HT(7) receptor. Determination of the pharmacophore for 5-HT(7) receptor agonism and CoMFA-based modeling of the agonist binding site.,  46  (25): [PMID:14640545] [10.1021/jm030826m]

15. Glennon RA, Jacyno JM, Salley JJ..  (1982)  2,3-dihydro and carbocyclic analogues of tryptamines: interaction with serotonin receptors.,  25  (1): [PMID:7086824] [10.1021/jm00343a013]

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18. May JA, Dantanarayana AP, Zinke PW, McLaughlin MA, Sharif NA..  (2006)  1-((S)-2-aminopropyl)-1H-indazol-6-ol: a potent peripherally acting 5-HT2 receptor agonist with ocular hypotensive activity.,  49  (1): [PMID:16392816] [10.1021/jm050663x]

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21. PubChem BioAssay data set, 

22. PubChem BioAssay data set, 

23. PubChem BioAssay data set, 

24. PubChem BioAssay data set, 

25. PubChem BioAssay data set, 

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27. Queiroz MM, Queiroz EF, Zeraik ML, Ebrahimi SN, Marcourt L, Cuendet M, Castro-Gamboa I, Hamburger M, da Silva Bolzani V, Wolfender JL..  (2014)  Chemical composition of the bark of Tetrapterys mucronata and identification of acetylcholinesterase inhibitory constituents.,  77  (3): [PMID:24521095] [10.1021/np401003p]

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35. Unpublished dataset, 

36. International Nonproprietary Names for Pharmaceutical Substances (INN), 

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• IMI-CARE SARS-CoV-2 Data
• International Nonproprietary Names