Exploring 5-MeO-T. To explore a different substance…

Names:
5-MeO-T · Mexamine · 5-Methoxytryptamine
IUPAC name:
2-(5-Methoxy-1H-indol-3-yl)ethan-1-amine
ID: 5143 · Formula: C11H14N2O · Molecular weight: 190.242
InChI: InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3

Taylor, EW; Nikam, S; Weck, B; Martin, A; Nelson, D. Relative selectivity of some conformationally constrained tryptamine analogs at 5-HT1, 5-HT1A and 5-HT2 recognition sites. Life Sci., 19 Oct 1987, 41 (16), 1961–1969. 622 kB. http://dx.doi.org/10.1016/0024-3205(87)90749-1

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 1 Oct 2014, 231 (21), 4135-4144. 298 kB. http://dx.doi.org/10.1007/s00213-014-3557-7

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2.2 MB. In German.

Wiseman-Distler, MH; Sourkes, TL. The effect of 4-hydroxyindoles on the metabolism of 5-hydroxytryptamine (serotonin). Ann. N. Y. Acad. Sci., 1 Jan 1962, 96, 142–151. 458 kB. http://dx.doi.org/10.1111/j.1749-6632.1962.tb50109.x

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 1 Dec 2013, 27 (12), 1690-1700. 929 kB. http://dx.doi.org/10.1002/bmc.2981

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. http://dx.doi.org/10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2.3 MB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. http://dx.doi.org/10.1021/jm950498t

McKenna, DJ. Monoamine oxidsase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12.2 MB.

Nichols, DE; Lloyd, DH; Johnson, MP; Hoffman, AJ. Synthesis and serotonin receptor affinities of a series of enantiomers of α-methyltryptamines: Evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors. J. Med. Chem., 1 Jan 1988, 31 (7), 1406–1412. 1.1 MB. http://dx.doi.org/10.1021/jm00402a026

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. http://dx.doi.org/10.1124/mol.107.039255

Glennon, RA; Titeler, M; Lyon, RA; Slusher, R. N,N-Di-n-propylserotonin: Binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem., 1 Jan 1988, 31 (4), 867–870. 600 kB. http://dx.doi.org/10.1021/jm00399a031

Glennon, RA; Chaurasia, C; Titeler, M. Binding of indolylalkylamines at 5-HT2 serotonin receptors: Examination of a hydrophobic binding region. J. Med. Chem., 1 Jan 1990, 33 (10), 2777–2784. 1.2 MB. http://dx.doi.org/10.1021/jm00172a016

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. http://dx.doi.org/10.1016/0006-2952(83)90281-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. http://dx.doi.org/10.1016/0014-2999(88)90432-3

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB.

Melatonin
5-MeO-DET
5-MeO-DIPT
5-MeO-DMT
5-MeO-MIPT
5-MeO-NMT
5-MeO-DPT
5-MeO-NCPT
N-Hexanoyl-5-MeO-T
N-Octanoyl-5-MeO-T
N-Heptafluorobutyroyl-5-MeO-T
5-MeO-DALT
5MT-NBOMe · 5MT-NB2OMe
5-MeO-EIPT
5-MeO-NALT
5-MeO-DPRT
5-MeO-MET
5MT-NB
5MT-NBOH
5MT-NB2OTFM
5MT-NB4OMe
5MT-NB4NO2
5MT-NB4NH2
5MT-NB4Me
5MT-NB4I
5-MeO-NBpBrT · 5MT-NB4B
5MT-NB4Cl
5MT-NB4F
5-MeO-NET
428
427
5-MeO-NIPT
5-MeO-MPT
5-MeO-EPT
5-MeO-DIBT
5-MeO-DBT
5-MeO-MIBT
5655
5657
5658
5659
5660
5661
5662
5663
5664
5665
5666
5667
5668
5669
5670
5671
5672
5673
5674
5675
5676
5677
5678
5679
5680
5681
5682
5683
5684
5685
5686
5687
5688
5689
5690
5691
5692
5694
5-MeO-MALT
5696
5697
5698
Methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate
tert-Butyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate
N2-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N2-methylglycinamide
5712
5713
5MT-NB3TFM
5MT-NB3Me
5MT-NB3I
5MT-NB3Cl
5MT-NB3F
5MT-NB3B
5MT-NB2B · 5MT-NBBr
5MT-NB3OMe
5MT-NB3SMe
5-MeO-α-MT
5-MeO-α-ET
1-iPr-5-MeO-T
5-MeO-2-Me-T · 2,O-DMS
4-Benzyloxy-5-MeO-T
4-F-5-MeO-DMT
T
5-HT · Serotonin
5-CT
5-BzO-T
5-Me-T
5-NoO-T
5-Ethyltryptamine
5-Acetyltryptamine
5750
5751
5752
5903
5902
5899
5898
5897
5896
5-CHeMeO-T
5-CHeO-T
5-CPeMeO-T
5-CPeO-T
5-HeO-T
5-PeO-T
5-IPrO-T
5-PrO-T
5849
5847
5846
5845
5844
5843
5842
5841
5840
6-HO-5-MeO-T
5-MeO-pyr-T
5-MeO-mor-T
5-MeO-pip-T
5-MeO-ICPA
N-HO-NMT
2-HO-NMT
4-HO-NMT
5-HO-NMT · Norbufotenine
4-HO-α-MT
5-HO-α-MT
1-Me-5-HT
4-MeO-T
5245
6-HO-AMT
2-Methylseroronin
HOT-T
Melatonin
5-MeO-DET
5-MeO-DIPT
5-MeO-DMT
5-MeO-MIPT
5-MeO-NMT
5-MeO-DPT
5-MeO-NCPT
N-Hexanoyl-5-MeO-T
N-Octanoyl-5-MeO-T
N-Heptafluorobutyroyl-5-MeO-T
5-MeO-DALT
5MT-NBOMe · 5MT-NB2OMe
5-MeO-EIPT
5-MeO-NALT
5-MeO-DPRT
5-MeO-MET
5MT-NB
5MT-NBOH
5MT-NB2OTFM
5MT-NB4OMe
5MT-NB4NO2
5MT-NB4NH2
5MT-NB4Me
5MT-NB4I
5-MeO-NBpBrT · 5MT-NB4B
5MT-NB4Cl
5MT-NB4F
5-MeO-NET
428
427
5-MeO-NIPT
5-MeO-MPT
5-MeO-EPT
5-MeO-DIBT
5-MeO-DBT
5-MeO-MIBT
5655
5657
5658
5659
5660
5661
5662
5663
5664
5665
5666
5667
5668
5669
5670
5671
5672
5673
5674
5675
5676
5677
5678
5679
5680
5681
5682
5683
5684
5685
5686
5687
5688
5689
5690
5691
5692
5694
5-MeO-MALT
5696
5697
5698
Methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate
tert-Butyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylglycinate
N2-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-N2-methylglycinamide
5712
5713
5MT-NB3TFM
5MT-NB3Me
5MT-NB3I
5MT-NB3Cl
5MT-NB3F
5MT-NB3B
5MT-NB2B · 5MT-NBBr
5MT-NB3OMe
5MT-NB3SMe
5-MeO-α-MT
5-MeO-α-ET
1-iPr-5-MeO-T
5-MeO-2-Me-T · 2,O-DMS
4-Benzyloxy-5-MeO-T
4-F-5-MeO-DMT
T
5-HT · Serotonin
5-CT
5-BzO-T
5-Me-T
5-NoO-T
5-Ethyltryptamine
5-Acetyltryptamine
5750
5751
5752
5903
5902
5899
5898
5897
5896
5-CHeMeO-T
5-CHeO-T
5-CPeMeO-T
5-CPeO-T
5-HeO-T
5-PeO-T
5-IPrO-T
5-PrO-T
5849
5847
5846
5845
5844
5843
5842
5841
5840
6-HO-5-MeO-T
5-MeO-pyr-T
5-MeO-mor-T
5-MeO-pip-T
5-MeO-ICPA
N-HO-NMT
2-HO-NMT
4-HO-NMT
5-HO-NMT · Norbufotenine
4-HO-α-MT
5-HO-α-MT
1-Me-5-HT
4-MeO-T
5245
6-HO-AMT
2-Methylseroronin
HOT-T
13 December 2017 · Creative Commons BY-NC-SA ·