Exploring T. To explore a different substance…

Names:
T · Tryptamine · Indole, 3-(2-aminoethyl) · 3-(2-Aminoethyl)indole
IUPAC name:
2-(1H-Indol-3-yl)ethan-1-amine
ID: 5053 · Formula: C10H12N2 · Molecular weight: 160.216
InChI: InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2

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

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. http://dx.doi.org/10.1002/qsar.19860050404

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.

Martins, CP; Awan, MA; Freeman, S; Herraiz, T; Alder, JF; Brandt, SD. Fingerprint analysis of thermolytic decarboxylation of tryptophan to tryptamine catalyzed by natural oils. J. Chromatogr. A, 7 Nov 2008, 1210 (1), 115–120. 450 kB. http://dx.doi.org/10.1016/j.chroma.2008.09.036

Brandt, SD; Mansell, D; Freeman, S; Fleet, IA; Alder, JF. Analytical characterisation of the routes by thermolytic decarboxylation from tryptophan to tryptamine using ketone catalysts, resulting in tetrahydro-β-carboline formation. J. Pharm. Biomed. Anal., 7 Jun 2006, 41 (3), 872–882. 610 kB. http://dx.doi.org/10.1016/j.jpba.2006.02.007

Ghosal, S; Srivastava, R. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry, 1 Jan 1973, 12 (1), 193–197. 552 kB. http://dx.doi.org/10.1016/S0031-9422(00)84646-4

Khalil, EM; De Angelis, J; Cole, PA. Indoleamine analogs as probes of the substrate selectivity and catalytic mechanism of serotonin N-acetyltransferase. J. Biol. Chem., 13 Nov 1998, 273 (46), 30321–30327. 247 kB. http://dx.doi.org/10.1074/jbc.273.46.30321

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

Speeter, ME; Anthony, WC. The action of oxalyl chloride on indoles: A new approach to tryptamines. J. Am. Chem. Soc., 1 Dec 1954, 76 (23), 6208–6210. 416 kB. http://dx.doi.org/10.1021/ja01652a113

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

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1.1 MB. http://dx.doi.org/10.1016/0028-3908(62)90015-1

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.

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

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture, countyourculture: rational exploration of the underground, 5 Dec 2011.

Meyers-Riggs, B. Alpha substituted tryptamines. countyourculture, countyourculture: rational exploration of the underground, 1 Mar 2012.

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

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3.1 MB. http://dx.doi.org/10.1007/BF02818560

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. http://dx.doi.org/10.1016/0024-3205(91)90582-V

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. http://dx.doi.org/10.1021/jm00190a014

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

Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916), 934–937. 529 kB. http://dx.doi.org/10.1126/science.1166127

DBT
DET
DIPT
DMT
DPT
EIPT
MBT
MIPT
NET
NMT
NIPT
N-HO-NMT
NCPT
PIPT
BIPT
MET
MPT
NPT
NBT
NIBT
NSBT
NTBT
NAT
NHT
DALT
5558
5559
N-Benzyltryptamine
5565
T-NBOMe
DIBT
EPT
MIBT
MSBT
DSBT
N-Formyltryptamine
5601
5602
5603
5604
5605
5606
5607
5608
5609
5610
5611
5612
5613
5614
5615
5616
5617
5618
5619
5620
5621
5622
5623
5624
5625
5626
5627
5628
5629
5630
5631
5632
5633
5634
5635
5636
5637
5638
5639
5640
5641
5642
5643
5645
5646
5647
5648
5649
5650
tert-Butyl N-[2-(1H-indol-3-yl)ethyl]-N-methylglycinate
N2-[2-(1H-Indol-3-yl)ethyl]-N2-methylglycinamide
5653
5654
DAT
DHT
HOT-T
α-ET
AMT · α-MT
α-PT
Tryptophan
α,α-DMT
α-Methyltryptophan
α-TFM-T
Norbaeocystin
4-HO-T
4-MeO-T
5-EtO-T
5485
5486
4-Cl-AMT
5-HT · Serotonin
5-MeO-T
5-CT
5-BzO-T
5-Me-T
5-NoO-T
5-Ethyltryptamine
5-Acetyltryptamine
5750
5751
5752
5903
5902
5899
5898
5897
5896
5858
5857
5856
5855
5854
5853
5852
5851
5849
5847
5846
5845
5844
5843
5842
5841
5840
5488
5494
6-HO-T
6-Chlorotryptamine
7-Me-T
7-Br-T
pyr-T
pip-T
mor-T
5073
5074
Gramine
dmpyrrol-T
mepipaz-T
Homotryptamine
DBT
DET
DIPT
DMT
DPT
EIPT
MBT
MIPT
NET
NMT
NIPT
N-HO-NMT
NCPT
PIPT
BIPT
MET
MPT
NPT
NBT
NIBT
NSBT
NTBT
NAT
NHT
DALT
5558
5559
N-Benzyltryptamine
5565
T-NBOMe
DIBT
EPT
MIBT
MSBT
DSBT
N-Formyltryptamine
5601
5602
5603
5604
5605
5606
5607
5608
5609
5610
5611
5612
5613
5614
5615
5616
5617
5618
5619
5620
5621
5622
5623
5624
5625
5626
5627
5628
5629
5630
5631
5632
5633
5634
5635
5636
5637
5638
5639
5640
5641
5642
5643
5645
5646
5647
5648
5649
5650
tert-Butyl N-[2-(1H-indol-3-yl)ethyl]-N-methylglycinate
N2-[2-(1H-Indol-3-yl)ethyl]-N2-methylglycinamide
5653
5654
DAT
DHT
HOT-T
α-ET
AMT · α-MT
α-PT
Tryptophan
α,α-DMT
α-Methyltryptophan
α-TFM-T
Norbaeocystin
4-HO-T
4-MeO-T
5-EtO-T
5485
5486
4-Cl-AMT
5-HT · Serotonin
5-MeO-T
5-CT
5-BzO-T
5-Me-T
5-NoO-T
5-Ethyltryptamine
5-Acetyltryptamine
5750
5751
5752
5903
5902
5899
5898
5897
5896
5858
5857
5856
5855
5854
5853
5852
5851
5849
5847
5846
5845
5844
5843
5842
5841
5840
5488
5494
6-HO-T
6-Chlorotryptamine
7-Me-T
7-Br-T
pyr-T
pip-T
mor-T
5073
5074
Gramine
dmpyrrol-T
mepipaz-T
Homotryptamine
24 July 2017 · Creative Commons BY-NC-SA ·