GramineCAS# 87-52-5 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 87-52-5 | SDF | Download SDF |
PubChem ID | 6890 | Appearance | White powder |
Formula | C11H14N2 | M.Wt | 174.25 |
Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
Synonyms | 3-(N,N-Dimethylaminomethyl)indole | ||
Solubility | DMSO : ≥ 125 mg/mL (717.40 mM) *"≥" means soluble, but saturation unknown. | ||
Chemical Name | 1-(1H-indol-3-yl)-N,N-dimethylmethanamine | ||
SMILES | CN(C)CC1=CNC2=CC=CC=C21 | ||
Standard InChIKey | OCDGBSUVYYVKQZ-UHFFFAOYSA-N | ||
Standard InChI | InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | Gramine has anti-tumor, anti-viral and anti-inflammatory properties; it can activate of antioxidants and inactivative of SOD in M. aeruginosa, it also has phytotoxicity on M. aeruginosa may be due to oxidative damage via oxidation of ROS . |
Targets | SOD | ROS | Antifection |
In vitro | Natural xenobiotics to prevent cyanobacterial and algal growth in freshwater: contrasting efficacy of tannic acid, gallic acid, and gramine.[Pubmed: 24332729]Chemosphere. 2014 Jun;104:212-20.Allelochemical action against planktonic phototrophs is one central issue in freshwater ecology and quality management. Gramine increase associated with rapid and transient systemic resistance in barley seedlings induced by mechanical and biological stresses.[Pubmed: 11673626]Plant Cell Physiol. 2001 Oct;42(10):1103-11.Systemic acquired resistance (SAR) is one of the intriguing issues for studying the mechanism in signal transduction system in a whole plant. We found that SAR and increase of an antifungal compound were induced rapidly and transiently in barley (Hordeum vulgare L. cv. Goseshikoku) by mechanical and biological stresses. One of the major antifungal compounds was identified as an indole alkaloid, Gramine (N,N-dimethyl-3-aminomethylindole), by mass spectrum and NMR analyses. |
In vivo | Synthesis, spectroscopy, theoretical and biological studies of new gramine-steroids salts and conjugates.[Pubmed: 25777948]Steroids. 2015 Jun;98:92-9.
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Kinase Assay | Gramine-induced growth inhibition, oxidative damage and antioxidant responses in freshwater cyanobacterium Microcystis aeruginosa.[Pubmed: 19131120]Aquat Toxicol. 2009 Feb 19;91(3):262-9.In recent years, the exploration and development of the effective methods of treatment and prevention to algal blooms, especially Microcystis aeruginosa blooms has been an important issue in the field of water environment protection. Allelochemicals (natural plant toxins) are considered promising sources of algicides to control algal blooms. |
Gramine Dilution Calculator
Gramine Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 5.7389 mL | 28.6944 mL | 57.3888 mL | 114.7776 mL | 143.472 mL |
5 mM | 1.1478 mL | 5.7389 mL | 11.4778 mL | 22.9555 mL | 28.6944 mL |
10 mM | 0.5739 mL | 2.8694 mL | 5.7389 mL | 11.4778 mL | 14.3472 mL |
50 mM | 0.1148 mL | 0.5739 mL | 1.1478 mL | 2.2956 mL | 2.8694 mL |
100 mM | 0.0574 mL | 0.2869 mL | 0.5739 mL | 1.1478 mL | 1.4347 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
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Natural xenobiotics to prevent cyanobacterial and algal growth in freshwater: contrasting efficacy of tannic acid, gallic acid, and gramine.[Pubmed:24332729]
Chemosphere. 2014 Jun;104:212-20.
Allelochemical action against planktonic phototrophs is one central issue in freshwater ecology and quality management. To determine some basic mechanisms of this toxic action, we exposed the coccal green alga, Desmodesmus armatus, and the coccal cyanobacterium, Microcystis aeruginosa, in a batch culture well-supplied with carbon dioxide to increasing concentrations of the polyphenols tannic acid and gallic acid and the alkaloid Gramine. The phototrophs were checked after 2d and at the end of the culture for biomass-based growth rates, cell volume, maximum quantum yield of photosystem II (PhiPSIImax), chlorophyll a content (chla) after 2d and at the end of the culture, and lipid peroxidation only at the end of the culture. During the culture, the pH rose from 7.64 to 10.95, a pH characteristic of eutrophic freshwater bodies during nuisance algal blooms. All xenobiotics reduced the growth rate, PhiPSIImax, and chla during the first 2d with M. aeruginosa being more sensitive to the polyphenols than D. armatus. The efficacy of the polyphenols declined with increasing pH, indicating potential polymerization and corresponding reduced bioavailability of the polyphenols. In contrast to the polyphenols, Gramine increased its toxic action over time, independent of the prevailing pH. All exposures caused slight to severe lipid peroxidation (LPO) in the phototrophs. Hence, one mechanism of growth inhibition may be oxidative stress-mediated reduction in photosynthesis. The presented results suggest that in successful field trials with leachate, the prevailing environmental conditions may inactivate polyphenols and xenobiotics other than polyphenols may be more effective.
Gramine increase associated with rapid and transient systemic resistance in barley seedlings induced by mechanical and biological stresses.[Pubmed:11673626]
Plant Cell Physiol. 2001 Oct;42(10):1103-11.
Systemic acquired resistance (SAR) is one of the intriguing issues for studying the mechanism in signal transduction system in a whole plant. We found that SAR and increase of an antifungal compound were induced rapidly and transiently in barley (Hordeum vulgare L. cv. Goseshikoku) by mechanical and biological stresses. One of the major antifungal compounds was identified as an indole alkaloid, Gramine (N,N-dimethyl-3-aminomethylindole), by mass spectrum and NMR analyses. Gramine is well known as a constitutive compound of barley, but it increased significantly in the primary and secondary leaves of barley seedlings within 12 h after pruning or inoculating with the powdery mildew fungi of barley (Blumeria graminis f.sp. hordei) and wheat (B. graminis f.sp. tritici). However, in the leaf detached from unwounded seedlings or in the leaf inoculated with the barley powdery mildew fungus, Gramine did not increase at all. In the water droplets contacted with barley leaves, the amount of leaked Gramine increased dependently upon the time after the seedling was injured mechanically. We also found a tight correlation between Gramine increase and enhancement of resistance to the barley powdery mildew fungus in barley leaves treated with an endogenous elicitor. Furthermore, such a systemic resistance was not observed in a barley cultivar Morex that lacks the biosynthetic pathway of Gramine. From these results, we conclude that Gramine is the excellent marker in rapid and transient systemic acquired resistance in barley.
Synthesis, spectroscopy, theoretical and biological studies of new gramine-steroids salts and conjugates.[Pubmed:25777948]
Steroids. 2015 Jun;98:92-9.
New Gramine connections with bile acids (lithocholic, deoxycholic, cholic) and sterols (cholesterol, cholestanol) were synthesized. The structures of products were confirmed by spectral (NMR, FT-IR) analysis, mass spectrometry (ESI-MS) as well as PM5 semiempirical methods. Unexpectedly, the products of the reaction of Gramine with cholesterol and cholestanol were symmetrical compounds consisting of two molecules of sterols connected by N(CH3)2 group. All new synthesized compounds interact in vitro with the human erythrocyte membrane and alter discoid erythrocyte shape inducing stomatocytosis or echinocytosis. Increase in the incorporation of the fluorescent dye merocyanine 540 (MC540) into the erythrocyte membrane indicates that new compounds at sublytic concentrations are capable of disturbing membrane phospholipids asymmetry and loosening the molecular packing of phospholipids in the bilayer. Gramine significantly decreases the membrane partitioning properties as well as haemolytic activity of lithocholic acid in its new salt. Moreover, both deoxycholic and cholic acids completely lost their membrane perturbing activities in the Gramine salts. On the other hand, the capacity of new Gramine-sterols connections to alter the erythrocyte membrane structure and its permeability is much higher in comparison with sterols alone. The dual effect of Gramine on the bile acid and sterols cell membrane partitioning activity observed in our study should not be neglected in vivo.
Gramine-induced growth inhibition, oxidative damage and antioxidant responses in freshwater cyanobacterium Microcystis aeruginosa.[Pubmed:19131120]
Aquat Toxicol. 2009 Feb 19;91(3):262-9.
In recent years, the exploration and development of the effective methods of treatment and prevention to algal blooms, especially Microcystis aeruginosa blooms has been an important issue in the field of water environment protection. Allelochemicals (natural plant toxins) are considered promising sources of algicides to control algal blooms. The objective of this study is to determine the inhibitory effects and potential mechanisms of a well-known allelochemical Gramine (N,N-dimethyl-3-amino-methylindole) on bloom-forming cyanobacterium M. aeruginosa. The results showed that this indole alkaloid effectively inhibited the growth of M. aeruginosa. The effective concentration causing a 50% inhibition at 3 d (EC(50, 3 d)) increased with the initial algal density (IAD) increasing. When IAD increased from 5x10(4) to 5x10(5)cellsmL(-1), the values of EC(50, 3 d) increased from 0.5 to 2.1mgL(-1). In the cells of M. aeruginosa, Gramine caused an obvious increase in the level of reactive oxygen species (ROS). The lipid-peroxidation product malondialdehyde (MDA) increased significantly in Gramine-treated cells. The effects of Gramine on enzymatic and non-enzymatic antioxidants were in different manners. The activity of superoxide dismutase (SOD) was decreased after Gramine exposure. The catalase (CAT) activity was increased after 4h but decreased from 60h. Both the contents and the regeneration rates of ascorbic acid (AsA) and reduced glutathione (GSH) were increased after 4h of exposure to Gramine. However, only GSH content was still increased after 40h of exposure. These results suggested that the activation of antioxidants in M. aeruginosa played an important role to resist the stress from Gramine at initial time, the inactivation of SOD is crucial to the growth inhibition of M. aeruginosa by Gramine, and the phytotoxicity of Gramine on M. aeruginosa may be due to oxidative damage via oxidation of ROS.