Exploring Serotonin. To explore a different substance…

Names:
5-HT · Serotonin · 5-Hydroxytryptamine
IUPAC name:
3-(2-Aminoethyl)-1H-indol-5-ol
ID: 5128 · Formula: C10H12N2O · Molecular weight: 176.215
InChI: InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2

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

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. http://dx.doi.org/10.1038/sj.bjp.0704747

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

Chilton, WS; Bigwood, J; Jensen, RE. Psilocin, Bufotenine and serotonin: Historical and biosynthetic observations. J. Psychoactive Drugs, 1 Jan 1979, 11 (1–2), 61–69. 9.5 MB. http://dx.doi.org/10.1080/02791072.1979.10472093

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

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. http://dx.doi.org/10.1124/jpet.106.103622

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

Schmid, CL; Bohn, LM. Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a β-arrestin2/Src/Akt signaling complex in vivo. J. Neurosci., 6 Oct 2010, 30 (40), 13513–13524. 1.5 MB. http://dx.doi.org/10.1523/JNEUROSCI.1665-10.2010

Regina, MJ. Biochemical changes associated with serotonergic hallucinogens. Ph. D. Thesis, State University of New York, Buffalo, NY, USA, 1 Jun 2005. 3.4 MB.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5.5 MB.

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

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.

Green, AR. Gaddum and LSD: the birth and growth of experimental and clinical neuropharmacology research on 5-HT in the UK. Br. J. Pharmacol., 1 Aug 2008, 1554 (8), 1583–1599. 418 kB. http://dx.doi.org/10.1038/bjp.2008.207

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

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

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

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. http://dx.doi.org/10.1002/cmdc.200800133

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

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

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

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

Sharp, T; Cowen, PJ. 5-HT and depression: is the glass half-full? Curr. Opin. Pharmacol., 1 Feb 2011, 11 (1), 45–51. 196 kB. http://dx.doi.org/10.1016/j.coph.2011.02.003

Lieberman, JA; Mailman, RB; Duncan, G; Sikich, L; Chakos, M; Nichols, DE; Kraus, JE. Serotonergic basis of antipsychotic drug effects in schizophrenia. Biol. Psychiat., 1 Dec 1998, 44 (11), 1099–1117. 154 kB. http://dx.doi.org/10.1016/S0006-3223(98)00187-5

Perez-Aguilar, JM; Shan, J; LeVine, MV; Khelashvili, G; Weinstein, H. A Functional Selectivity Mechanism at the Serotonin-2A GPCR Involves Ligand-Dependent Conformations of Intracellular Loop 2. J. Am. Chem. Soc., 12 Nov 2014, 136 (45), 16044–16054. 4.2 MB. http://dx.doi.org/10.1021/ja508394x

Macor, JE; Fox, CB; Johnson, C; Koe, BK; Lebel, LA; Zorn, SH. 1-(2-Aminoethyl)-3-methyl-8,9-dihydropyrano[3,2-e]indole: A rotationally restricted phenolic analog of the neurotransmitter serotonin and agonist selective for serotonin (5-HT2-type) receptors. J. Med. Chem., 1 Jan 1992, 35 (20), 3625–3632. 1.9 MB. http://dx.doi.org/10.1021/jm00098a005

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. http://dx.doi.org/10.1021/jm00321a017

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5.9 MB.

5-HO-DMT
5-HO-NMT · Norbufotenine
Normelatonin
5-HO-DIPT
5-HTP · 5-Hydroxytryptophan
5-HO-α-MT
1-Me-5-HT
2-Methylseroronin
T
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
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
5,6-Dihydroxytryptamine
5,7-DHT
4-HO-T
6-HO-T
5-HO-DMT
5-HO-NMT · Norbufotenine
Normelatonin
5-HO-DIPT
5-HTP · 5-Hydroxytryptophan
5-HO-α-MT
1-Me-5-HT
2-Methylseroronin
T
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
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
5,6-Dihydroxytryptamine
5,7-DHT
4-HO-T
6-HO-T
24 November 2017 · Creative Commons BY-NC-SA ·