Explore Tryptophan | TiHKAL · info

Exploring Tryptophan. To explore a different substance…

Names

Tryptophan
Trp
α-Carboxytryptamine

IUPAC names

L-Tryptophan
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid

ID 5148 · Formula C₁₁H₁₂N₂O₂ · Molecular weight 204.225

Tags Tryptamine

InChI InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1

InChI Key QIVBCDIJIAJPQS-VIFPVBQESA-N This stereoisomer Any stereoisomer

SMILES OC(=O)[C@H](Cc1c[nH]c2c1cccc2)N

ChemSpider 6066
PubChem 6305
Wikidata Q181003
Wikipedia Tryptophan

TiHKAL #6 DMT · #11 α-ET · #44 6-MeO-THH · #48 α-MT · #53 T

Phenethylamine: Von der Strucktur zur Funktion Tryptophan: 3.13 (5) 270

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

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

Fenderson5555. DMT from tryptophan? , 23 Mar 2011. . Fenderson5555 3.9 MB. Big hug to W. Snow for kindly filling this gap in the collection.

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. https://doi.org/10.1002/bmc.2981

Fricke, J; Blei, F; Hoffmeister, D. Enzymatic synthesis of psilocybin. Angew. Chem. Int., 20 Aug 2017, 56 (40), 12352-12355. 1.8 MB. https://doi.org/10.1002/anie.201705489

Collins, M. Some new psychoactive substances: Precursor chemical and synthesis-driver end-products. Drug Test. Anal., 1 Jul 2001, 3 (7–8), 404–416. 178 kB. https://doi.org/10.1002/dta.315

Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 879 kB. https://doi.org/10.1007/7854_2016_466

Helm, K. Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT_2A-Rezeptors aus der Klasse. Ph. D. Thesis, Universität Regensburg, Dresden, 1 Jan 2014. 3.2 MB. #2 LC,MS,NMR,IR

Jakubczyk, D; Cheng, JZ; O'Connor, SE. Biosynthesis of the ergot alkaloids. Nat. Prod. Rep., 28 Aug 2014, 31 (10), 1328-1338. 476 kB. https://doi.org/10.1039/C4NP00062E #7

Parker, G; Brotchie, H. Mood effects of the amino acids tryptophan and tyrosine: ‘Food for Thought’ III. Acta Psychiatr. Scand., 1 Jan 2011, 124 (6), 417-426. 123 kB. https://doi.org/10.1111/j.1600-0447.2011.01706.x

Barker, SA. N,N-dimethyltryptamine (DMT), an endogenous hallucinogen: Past, present, and future research to determine its role and function. Front. Neurosci., 6 Aug 2018, 12 (536). 1.0 MB. https://doi.org/10.3389/fnins.2018.00536 #Tryptophan

Nichols, DE. N,N-Dimethyltryptamine and the pineal gland: Separating fact from myth. J. Psychopharmacol., 1 Jan 2018, 32 (1), 30–36. 456 kB. https://doi.org/10.1177/0269881117736919 #Tryptophan

Dean, JG. Indolethylamine-N-methyltransferase polymorphisms: Genetic and biochemical approaches for study of endogenous N,N-dimethyltryptamine. Front. Neurosci., 23 Apr 2018, 12 (232). 2.1 MB. https://doi.org/10.3389/fnins.2018.00232 #L-tryptophan

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77 (4), 1245–1272. 1.2 MB. https://doi.org/10.1016/j.talanta.2008.07.062 #TP

Hoffer, A; Osmond, H. The Hallucinogens, Academic Press, New York, . 3.9 MB. #a-Tryptophan

Cameron, LP; Olson, DE. DARK classics in chemical neuroscience: N,N-Dimethyltryptamine (DMT). ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2344–2357. 1.4 MB. https://doi.org/10.1021/acschemneuro.8b00101 #14

Geiger, HA; Wurst, MG; Daniels, RN. DARK classics in chemical neuroscience: Psilocybin. ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2438–2447. 580 kB. https://doi.org/10.1021/acschemneuro.8b00186 #7

Fricke, J; Lenz, C; Wick, J; Blei, F; Hoffmeister, D. Production options for psilocybin: Making of the magic. Chem. Eur. J., 18 Jan 2019, 25 (4), 897–903. 1.8 MB. https://doi.org/10.1002/chem.201802758 #8

Blei, F; Baldeweg, F; Fricke, J; Hoffmeister, D. Biocatalytic production of psilocybin and derivatives in tryptophan synthase-enhanced reactions. Chem. Eur. J., 17 Jul 2018, 24 (40), 10028–10031. 969 kB. https://doi.org/10.1002/chem.201801047 #1 LC,MS,NMR

Torrens-Spence, MP; Liu, C; Pluskal, T; Chung, YK; Weng, J. Monoamine biosynthesis via a noncanonical calcium-activatable aromatic amino acid decarboxylase in psilocybin mushroom. ACS Chem. Biol., 21 Dec 2018, 13 (12), 3343–3353. 5.9 MB. https://doi.org/10.1021/acschembio.8b00821 #L-Trp other

Lenz, C; Wick, J; Hoffmeister, D. Identification of ω-N-methyl-4-hydroxytryptamine (Norpsilocin) as a Psilocybe natural product. J. Nat. Prod., 27 Oct 2017, 80 (10), 2835–2838. 1.1 MB. https://doi.org/10.1021/acs.jnatprod.7b00407 #Tryptophan LC,MS,NMR

Milne, N; Thomsen, P; Knudsen, NM; Rubaszka, P; Kristensen, M; Borodina, I. Metabolic engineering of Saccharomyces cerevisiae for the de novo production of psilocybin and related tryptamine derivatives. Metab. Eng., 1 Jul 2020, 60, 25–36. 2.4 MB. https://doi.org/10.1016/j.ymben.2019.12.007 #Tryptophan LC,MS

Nichols, DE. Psilocybin: From ancient magic to modern medicine. J. Antibiot., 1 Oct 2020, 73 (10), 679-686. 774 kB. https://doi.org/10.1038/s41429-020-0311-8

Lenz, C; Sherwood, A; Kargbo, R; Hoffmeister, D. Taking different roads: L‐Tryptophan as the origin of Psilocybe natural products. ChemPlusChem, 1 Jan 2021, 86 (1), 28–35. 793 kB. https://doi.org/10.1002/cplu.202000581 #tryptophan

Nakagawasai, O; Arai, Y; Satoh, S; Satoh, N; Neda, M; Hozumi, M; Oka, R; Hiraga, H; Tadano, T. Monoamine oxidase and head-twitch response in mice: Mechanisms of α-methylated substrate derivatives. Neurotoxicology, 1 Jan 2004, 25 (1), 223–232. 169 kB. https://doi.org/10.1016/S0161-813X(03)00101-3 #Tryptophan

Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #4.2

Fenozolone

CL-39808 · Thozalinone · Tozalinone

7117

8398

7 Dec 2019 · · Isomer Design