Tryptamine

Manufactured by Merck Group

Sourced in United States, Germany

Tryptamine is a laboratory compound used as a precursor in the synthesis of various pharmaceutical and research chemicals. It is a naturally occurring organic compound with a core indole structure. Tryptamine serves as a foundation for the development of diverse chemical derivatives and is utilized in various analytical and synthetic applications within professional laboratory settings.

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Lab products found in correlation

Tyramine, by Merck Group (15 mentions) Cadaverine, by Merck Group (13 mentions) Histamine, by Merck Group (12 mentions) Putrescine, by Merck Group (11 mentions) Serotonin, by Merck Group (11 mentions) Putrescine dihydrochloride, by Merck Group (10 mentions) Spermine, by Merck Group (10 mentions) Cadaverine dihydrochloride, by Merck Group (9 mentions) Histamine dihydrochloride, by Merck Group (9 mentions) Spermidine, by Merck Group (9 mentions) Tyramine hydrochloride, by Merck Group (7 mentions) Spermine tetrahydrochloride, by Merck Group (7 mentions) Spermidine trihydrochloride, by Merck Group (7 mentions) Tryptophan, by Merck Group (6 mentions) 1 7 diaminoheptane, by Merck Group (5 mentions) Methylamine, by Merck Group (5 mentions) Phenethylamine, by Merck Group (5 mentions) Glutamine, by Merck Group (5 mentions) L tryptophan, by Merck Group (5 mentions) β phenylethylamine hydrochloride, by Merck Group (4 mentions)

Close spelling variants of this product

Tryptamine hydrochloride

53 protocols using tryptamine

Indole-3-Acetic Acid Assimilation in Caballeronia glathei

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All IAA derivatives used in this study (indole-3-acetic acid, 3-(2-hydroxyethyl)indole, ethyl-3-indole-acetate, 3-(3-hydroxypropyl)indole, 3-indoleacetonitrile, indole-3-acetamide, indole-3-butyric acid, DL-indole-3-lactic acid, indole-3-propionic acid, tryptamine, indole-3-acrycil acid and indole-3-carboxylic acid) and H₂¹⁸O were purchased from Sigma-Aldrich. All cloning and protein expression reagents were from ThermoFisher Scientific (Vilnius, Lithuania). All other reagents used in this study were of analytical or higher grade.
Caballeronia glathei strain DSM50014 was obtained from the German Collection of Microorganisms and Cell Cultures (DSMZ), Braunschweig, Germany. This strain was routinely cultivated in M1 medium (5 g L⁻¹ peptone, 3 g L⁻¹ meat extract, pH 7). For the IAA assimilation experiments, C. glathei DSM50014 was cultivated in M9 medium (3.5 g L⁻¹ Na₂HPO₄, 1.5 g L⁻¹ KH₂PO₄, 2.5 g L⁻¹ NaCl, 0.2 g L⁻¹ MgSO₄, 0.01 g L⁻¹ CaCl₂). Escherichia coli strains used in this study are listed in Supplementary Table S2. All E. coli strains were cultivated in LB medium. Ampicillin (50 μg mL⁻¹) and streptomycin (30 μg mL⁻¹) were added when necessary.

Sadauskas M., Statkevičiūtė R., Vaitekūnas J, & Meškys R. (2020). Bioconversion of Biologically Active Indole Derivatives with Indole-3-Acetic Acid-Degrading Enzymes from Caballeronia glathei DSM50014. Biomolecules, 10(4), 663.

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Cell Culture and Reagent Sourcing

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The bacterial culture medium, Difco LB broth Miller (Luria−Bertani), was obtained from Becton, Dickinson, and Company (Sparks, MD, USA). The Ni-NTA resin and gel-filtration column (Superdex-75) were obtained from GE Healthcare (GE Healthcare Life Sciences, USA). All other chemicals used for buffer preparation were analytical grade and obtained from SRL Chemicals (India). Dulbecco’s modified eagle’s media (DMEM), RPMI-1640 and F-12K cell culture medium, antibiotic antimycotic cocktail (penicillin, streptomycin, and amphotericin-B), fetal bovine serum (FBS), MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide) and cell detachment enzyme (TrypLE express) were purchased from Gibco-life technologies, Thermo Fisher Scientific (USA). Hordenine, vincamine, tryptamine, cinchonine, and colcemid were purchased from Sigma-Aldrich Chemical Co. Bengaluru, India (now Merck KGaA, Darmstadt, Germany). Human adenocarcinoma alveolar basal epithelial cells (A549), lung metastatic cell line (H1299), and human embryonic kidney cells (HEK293) were obtained from the National Centre for Cell Sciences, Pune, India.

Anwar S., Mohammad T., Shamsi A., Queen A., Parveen S., Luqman S., Hasan G.M., Alamry K.A., Azum N., Asiri A.M, & Hassan M.I. (2020). Discovery of Hordenine as a Potential Inhibitor of Pyruvate Dehydrogenase Kinase 3: Implication in Lung Cancer Therapy. Biomedicines, 8(5), 119.

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Biogenic Amine Quantification Protocol

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Tryptamine, β-phenylethylamine hydrochloride, putrescine dihydrochloride, cadaverine dihydrochloride, histamine dihydrochloride, tyramine hydrochloride, spermidine trihydrochloride, and spermine tetrahydrochloride (all Sigma-Aldrich) were used for standard solutions, and 1,7-diaminoheptane (Sigma-Aldrich) was applied for an internal standard. The concentrations of all standard solutions were adjusted to 0, 10, 50, 100, and 1000 ppm.

Jin Y.H., Lee J.H., Park Y.K., Lee J.H, & Mah J.H. (2019). The Occurrence of Biogenic Amines and Determination of Biogenic Amine-Producing Lactic Acid Bacteria in Kkakdugi and Chonggak Kimchi. Foods, 8(2), 73.

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Chemicals for Neurochemical Analysis

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Tryptophan, tryptamine, serotonin, cinnamic acid, coumaric acid, caffeic acid, ferulic acid, sinpaic acid, dichloromethane, and other chemicals, were purchased from Sigma Chemical Co. (St. Louis, MO, USA).

, & Park J.B. (2017). In Silico Screening and In Vitro Activity Measurement of Javamide Analogues as Potential p38 MAPK Inhibitors. International Journal of Molecular Sciences, 18(12), 2704.

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Measuring Mitochondrial Activity in CD34+ Cells

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Mitochondrial activity within CD34⁺ cells was measured using the MitoPlate S-1 (Biolog, California, US) following the manufacturer’s instructions. Briefly, plate substrates were fully dissolved using an assay mix containing Biolog MAS (Biolog, California, US), redox dye MC (Biolog, California, US) and 45 µg/ml saponin (Sigma-Aldrich, Missouri, US) for 1 h at 37 °C. CD34⁺ cells were washed with twice with PBS, resuspended in MAS at a density of 6 × 10⁴ cells/30 µL and added to wells. Kinetic reading at 590 nm was done using infinite pro 200 plate reader (TECAN, Männedorf, Switzerland). Background readings (no substrate) were subtracted from absorbance readings.
Activity of isolated mitochondria was measured using empty plates (Biolog, California, US) coated with 10 mM tryptamine (Sigma-Aldrich, Missouri, US). 40 µg of isolated mitochondria was resuspended in Biolog MAS. Kinetic reading at 590 nm was done using infinite pro 200 plate reader (TECAN, Männedorf, Switzerland). Background readings (no substrate) were subtracted from absorbance readings.

Jacoby E., Ben Yakir-Blumkin M., Blumenfeld-Kan S., Brody Y., Meir A., Melamed-Book N., Napso T., Pozner G., Saadi E., Shabtay-Orbach A., Yivgi-Ohana N., Sher N, & Toren A. (2021). Mitochondrial augmentation of CD34+ cells from healthy donors and patients with mitochondrial DNA disorders confers functional benefit. NPJ Regenerative Medicine, 6, 58.

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Indolic Compound Extraction and Analysis

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The indolic compounds tryptophan, tryptamine, 5HTryp, NAT, serotonin, NAS, and 5MT were purchased from Sigma-Aldrich (Madrid, Spain) and Shanghai Yuanye Bio-Technology Co., Ltd (China). These indolic compounds were extracted using the method described in our previous study (Wang et al., 2020a (link)). Briefly, sample tissues (0.5g) from the CR and control (CK) groups was finely ground, followed by extraction in an 1ml buffer containing 50% methanol and 0.1% formic acid for 15min in a shaker. After ultrasound treatment for 30min in an ice bath, the mixtures were incubated at 4°C for 30min and then centrifuged for 20min at 12,000rpm. The extracts were filtered through a 0.3μm filter membrane and were analyzed using LC–MS/MS platform (Waters Iclass-AB Sciex 6500) platform at Beijing Genomics Institute (BGI)-Shenzhen (Wuhan, China) as described by Sara et al. (2019) (link).

Wang G., Chen X., Zhang C., Li M., Sun C., Zhan N., Huang X., Li T, & Deng W. (2021). Biosynthetic Pathway and the Potential Role of Melatonin at Different Abiotic Stressors and Developmental Stages in Tolypocladium guangdongense. Frontiers in Microbiology, 12, 746141.

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Chemical Reagents Procurement for Research

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Chemicals and reagents such as tryptophan and tryptamine that were used in this study were purchased from Sigma-Aldrich (St. Louis, MO, USA) or Aladdin (Shanghai, China). Kanamycin was purchased from Melonepharm (Dalian, China) and yeast extract and tryptone were from OXOID (Basingstoke, UK). KOD-Plus-Neo was purchased from TOYOBO (Shanghai, China).

Zhou Y., Liao L., Liu X., Liu B., Chen X., Guo Y., Huang C., Zhao Y, & Zeng Z. (2020). Crystal structure of Oryza sativa TDC reveals the substrate specificity for TDC-mediated melatonin biosynthesis. Journal of Advanced Research, 24, 501-511.

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Enzymatic Synthesis and Purification of Strictosidine

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Strictosidine synthase was purified as in 48 (link). Strictosidine was generated enzymatically by incubation of 4 mM tryptamine (Sigma), 2 mM purified secologanin (Sigma) and 2 µM strictosidine synthase in 50 mM phosphate buffer pH 7.4 buffer, in a total volume of 50 ml, overnight at 37 °C. This reaction was monitored for strictosidine production and consumption of secologanin by LC-MS. The solution was purified by solid phase extraction, eluted in 100% MeOH, and dried under vacuum. The dried product was resuspended in H₂O, filtered with 2 µm filters and purified by preparative HPLC in 2 ml aliquots. The HPLC used was a Dionex Ultimate 3000 pump, with a variable wavelength UV detector. The column used for chromatographic separation was a Phenomenex Luna 5µ C18(2) 100 A (250 x 30 mm), with the binary solvent system consisting of 0.1% TFA and acetonitrile. The elution program was the following: 1 min isocratic at 10% ACN, 8 min gradient up to 30% ACN, 4 min gradient up to 100% ACN, 6 min isocratic at 100% ACN, 1 min gradient down to 10% ACN, and 6 min isocratic at 10% ACN. The compounds were monitored by UV 241 nm, and the fractions collected at the retention time 13.5 min. The resulting fractions were lyophilized and analyzed by NMR.

Payne R.M., Xu D., Foureau E., Teto Carqueijeiro M.I., Oudin A., de Bernonville T.D., Novak V., Burow M., Olsen C.E., Jones D.M., Tatsis E.C., Pendle A., Halkier B.A., Geu-Flores F., Courdavault V., Nour-Eldin H.H, & O’Connor S.E. (2017). An NPF Transporter Exports a Central Monoterpene Indole Alkaloid Intermediate from the Vacuole. Nature plants, 3, 16208.

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Synthesis and Characterization of Psychoactive Compounds

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Bupropion hydrochloride and 6-hydroxybupropion were obtained from Toronto Research Chemicals (Toronto, Canada), ibogaine from Ibogaworld, cocaine from Medisca (Montreal, Canada), β-PEA, pinoline, indole, tryptamine, ephedrine, frovatriptan, alprenolol, isoproterenol, evodiamine, and tyramine from Sigma (Oakville, Canada), fluoxetine and amphetamine were from Tocris Bioscience (Bristol, United Kingdom). PAL analogs, RTI analogs, and bicifadine were synthesized at RTI in the Blough laboratory as described previously (Carroll et al., 2009 (link), 2011 (link); Blough et al., 2011 , 2014 (link)). Noribogaine (Batch No. 606950002) was from Deborah Mash, Ph.D. (Obach et al., 1998 ). Ibogamine was obtained from Specs (Zoetermeer, The Netherlands). Sodium phenylbutyrate was purchased from Enzo Life Sciences Inc. (Farmingdale, NY). Ibogaminalog, ibogainealog, noribogainalog, fluorogainalog, and tabernanthalog were synthesized in the lab of David E. Olson (Cameron et al., 2020 (link)).

Sutton C., Williams E.Q., Homsi H., Beerepoot P., Nazari R., Han D., Ramsey A.J., Mash D.C., Olson D.E., Blough B, & Salahpour A. (2022). Structure-Activity Relationships of Dopamine Transporter Pharmacological Chaperones. Frontiers in Cellular Neuroscience, 16, 832536.

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Synthesis and Characterization of Tryptamine-based Complexes

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All the reagents and chemicals used for the synthesis were of analytical grade and were purchased from commercial sources. They were used as received without further purification. Tryptamine and 2-hydroxynepthaldehyde were purchased from Sigma Aldrich. 1,10-Phenanthroline and metal chlorides were purchased from Merck.
Microanalyses (C, H and N) was carried out with FlashEA 1112 elemental analyzer (Thermo Scientific). The molar conductance at room temperature were measured on a Syntronics type 302 conductivity bridge equilibrated at 25 ± 0.01 °C. For conductivity measurements one millimolar solutions in DMSO were prepared. Electrothermal melting point apparatus was used to determine the melting point of the synthesized compounds. FT-IR spectra of the synthesized compounds were recorded using KBr pellets on a Perkin-Elmer 283 spectrophotometer. For ¹H NMR and ¹³C NMR measurements Brucker WH 300 (200 MHz) and Brucker WH 270 (67.93 MHz) were used using CDCl₃ or DMSO-d₆ as a solvent and trimethylsilane as an internal standard. ESI-MS (AB-Sciex 2000, Applied Biosystem) was used to record mass spectra of the synthesized ligand and complexes.

Dar O.A., Lone S.A., Malik M.A., Wani M.Y., Ahmad A, & Hashmi A.A. (2019). New transition metal complexes with a pendent indole ring: insights into the antifungal activity and mode of action. RSC Advances, 9(27), 15151-15157.

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