ID: ALA7257

Max Phase: Phase

Molecular Formula: C13H18N2O

Molecular Weight: 218.30

Molecule Type: Small molecule

Representations

Synonyms (5): 5-meo-dmt | 5-methoxy-n-dimethyltryptamine | 5-methoxydimethyltryptamine | Mebufotenin | NSC-88624
Synonyms from Alternative Forms(5):

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

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

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: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

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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10. Glennon RA, Hong SS, Bondarev M, Law H, Dukat M, Rakhi S, Power P, Fan E, Kinneau D, Kamboj R, Teitler M, Herrick-Davis K, Smith C..  (1996)  Binding of O-alkyl derivatives of serotonin at human 5-HT1D beta receptors.,  39  (1): [PMID:8568822] [10.1021/jm950498t]

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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]

16. Glennon RA, Titeler M, Lyon RA, Slusher RM..  (1988)  N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin.,  31  (4): [PMID:2965244] [10.1021/jm00399a031]

17. Kline TB, Benington F, Morin RD, Beaton JM..  (1982)  Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety.,  25  (8): [PMID:7120280] [10.1021/jm00350a005]

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]

19. Kolanos R, Dukat M, Roth BL, Glennon RA..  (2006)  Interaction of N1-unsubstituted and N1-benzenesulfonyltryptamines at h5-HT6 receptors.,  16  (22): [PMID:16945532] [10.1016/j.bmcl.2006.08.068]

20. Yu L, Ho L, Liao J, Chen C.  (1997)  Two 5-HT 1A Receptor-Interactive Tryptamine Derivatives from the Unripe Fruit of Evodia rutaecarpa ,  60  (11): [10.1021/np960678l]

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, 

26. Pullagurla M, Dukat M, Roth BL, Setola V, Glennon RA.  (2005)  5-ZATRYPTAMINE ANALOGS AS h5-HT6 SEROTONIN RECEPTOR LIGANDS,  14  (1): [10.1007/s00044-004-0121-8]

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]

28. Glennon RA, Gessner PK, Godse DD, Kline BJ..  (1979)  Bufotenine esters.,  22  (11): [PMID:533890] [10.1021/jm00197a025]

29. Glennon RA, Liebowitz SM, Mack EC..  (1978)  Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues.,  21  (8): [PMID:278843] [10.1021/jm00206a022]

30. de la Fuente Revenga M, Fernández-Sáez N, Herrera-Arozamena C, Morales-García JA, Alonso-Gil S, Pérez-Castillo A, Caignard DH, Rivara S, Rodríguez-Franco MI..  (2015)  Novel N-Acetyl Bioisosteres of Melatonin: Melatonergic Receptor Pharmacology, Physicochemical Studies, and Phenotypic Assessment of Their Neurogenic Potential.,  58  (12): [PMID:26023814] [10.1021/acs.jmedchem.5b00245]

31. Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, Myers-Turnbull D, Taylor JC, Grodzki AC, Lein PJ, Kokel D, Olson DE..  (2020)  Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies.,  63  (3): [PMID:31977208] [10.1021/acs.jmedchem.9b01404]

32. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

33. Kargbo RB..  (2021)  The Psychedelic Renaissance: Addressing Potential Adverse Effects in a Therapeutic Setting.,  12  (12.0): [PMID:34917241] [10.1021/acsmedchemlett.1c00577]

34. Kargbo RB..  (2022)  Improved Metabolically Stable 5-HT Receptor Modulators and the Development of New Antidepressants.,  13  (4.0): [PMID:35450349] [10.1021/acsmedchemlett.2c00129]

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