Tryptamine
(Synonyms: 色胺) 目录号 : GC33630
An indole alkaloid
Cas No.:61-54-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Tryptamine is an indole alkaloid and intermediate in the biosynthesis of serotonin and the phytohormone melatonin in plants.1,2 It increases the levels of the terpenoid indole alkaloids ajmalicine, strictosidine, and catharanthine in cultures of C. roseus.3 Tryptamine is also a product of tryptophan metabolism in mammals.4 Tryptamine derivatives have been synthetically produced as hallucinogenic drugs of abuse that act on the serotonergic system.5
1.Arnao, M.B.Phytomelatonin: Discovery, content, and role in plantsAdv. Bot.2014:815769(2014) 2.Fan, J., Xie, Y., Zhang, Z., et al.Melatonin: A multifunctional factor in plantsInt. J. Mol. Sci.19(5)E1528(2018) 3.Almagro, L., Fernández-Pérez, F., and Pedre?o, M.A.Indole alkaloids from Catharanthus roseus: Bioproduction and their effect on human healthMolecules20(2)2973-3000(2015) 4.Berumen, L.C., Rodríguez, A., Miledi, R., et al.Serotonin receptors in hippocampusSci. World J.2012:823493(2012) 5.Araujo, A.M., Carvalho, F., Bastos, M.L., et al.The hallucinogenic world of tryptamines: An updated reviewArch. Toxicol.89(8)1151-1173(2015)
| Cas No. | 61-54-1 | SDF | |
| 别名 | 色胺 | ||
| Canonical SMILES | NCCC1=CNC2=C1C=CC=C2 | ||
| 分子式 | C10H12N2 | 分子量 | 160.22 |
| 溶解度 | DMSO : ≥ 150 mg/mL (936.21 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.2414 mL | 31.2071 mL | 62.4142 mL |
| 5 mM | 1.2483 mL | 6.2414 mL | 12.4828 mL |
| 10 mM | 0.6241 mL | 3.1207 mL | 6.2414 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Tryptamine: a metabolite of tryptophan implicated in various neuropsychiatric disorders
Metab Brain Dis 1993 Mar;8(1):1-44.PMID:8098507DOI:10.1007/BF01000528.
Although early interest in the biomedical relevance of Tryptamine has waned in recent years, it is clear from the above discussion that the study of Tryptamine is worthy of serious consideration as a factor in neuropsychiatric disorders. The study of [3H]-tryptamine binding sites indicates an adaptive responsiveness characteristic of functional receptors. The question raised by Jones (1982d) on whether Tryptamine is acting centrally as a neurotransmitter or a neuromodulator still remains mostly unanswered, although the evidence cited within this review strongly suggests a modulatory role for this neuroactive amine (see also Juorio and Paterson, 1990). The synthesis and degradative pathways of Tryptamine, as well as the intricate neurochemical and behavioral consequences of altering these pathways, are now more fully understood. It is not yet clear what the role of Tryptamine is under normal physiological [homeostatic] conditions, however, its role during pathological conditions such as mental and physical stress, hepatic dysfunction and other disorders of metabolism (i.e. electrolyte imbalance, increased precursor availability, enzyme induction or alterations in enzyme co-factor availability) may be quite subtle, perhaps accounting for various sequelae hitherto considered idiopathic. The evidence for a primary role for Tryptamine in the etiology of mental or neurological diseases is still relatively poor, although the observations that endogenous concentrations of Tryptamine are particularly susceptible to pharmacological as well as physiological manipulations serve to reinforce the proposition that this indoleamine is not simply a metabolic accident but rather a neuroactive compound in its own right. Finally, one might wonder what proportion of the data attributed to modifications of 5-HT metabolism might, in fact, involve unrecognized changes in the concentrations of other neuroactive metabolites of tryptophan such as Tryptamine.
Electrophilic Thiocyanation of Tryptamine Derivatives: Divergent Synthesis of SCN-Containing Indole Compounds
Chem Asian J 2022 Nov 2;17(21):e202200802.PMID:36039929DOI:10.1002/asia.202200802.
A tandem dearomative electrophilic thiocyanation/cyclization/acylation of indoles was developed for the first time, which is enabled by acyl chloride. A variety of 3-SCN pyrroloindolines were obtained with moderate to excellent yields. Interestingly, following replacement of acyl chloride with methanesulfonic acid, 2-SCN tryptamines were obtained using the same starting substrates and reagents. Furthermore, catalytic enantioselective manner of thiocyanation/cyclization/acylation reaction was also studied. An enantiomer self-disproportionation effect of 3-SCN pyrroloindolines was discovered. A series of chiral 3-SCN pyrroloindolines were obtained with high enantioselectivities.
Tryptamine, a Microbial Metabolite in Fermented Rice Bran Suppressed Lipopolysaccharide-Induced Inflammation in a Murine Macrophage Model
Int J Mol Sci 2022 Sep 23;23(19):11209.PMID:36232510DOI:10.3390/ijms231911209.
Fermentation is thought to alter the composition and bioavailability of bioactive compounds in rice bran. However, how this process affects the anti-inflammatory effects of rice bran and the bioactive compounds that might participate in this function is yet to be elucidated. This study aimed to isolate bioactive compounds in fermented rice bran that play a key role in its anti-inflammatory function. The fermented rice bran was fractionated using a succession of solvent and solid-phase extractions. The fermented rice bran fractions were then applied to lipopolysaccharide (LPS)-activated murine macrophages to evaluate their anti-inflammatory activity. The hot water fractions (FRBA), 50% ethanol fractions (FRBB), and n-hexane fractions (FRBC) were all shown to be able to suppress the pro-inflammatory cytokine expression from LPS-stimulated RAW 264.7 cells. Subsequent fractions from the hot water fraction (FRBF and FRBE) were also able to reduce the inflammatory response of these cells to LPS. Further investigation revealed that Tryptamine, a bacterial metabolite of tryptophan, was abundantly present in these extracts. These results indicate that Tryptamine may play an important role in the anti-inflammatory effects of fermented rice bran. Furthermore, the anti-inflammatory effects of FRBE and Tryptamine may depend on the activity of the aryl hydrocarbon receptor.
Interaction of psychedelic Tryptamine derivatives with a lipid bilayer
Chem Phys Lipids 2023 Mar;251:105279.PMID:36627076DOI:10.1016/j.chemphyslip.2023.105279.
Naturally occurring psychedelics have been used for a long time as remedies or in religious ceremonies and recreational activities. Recent studies have proven the therapeutic potential of some psychedelic compounds to safely treat a wide range of diseases such as anxiety, depression, migraine, and addiction. It is hypothesized that psychedelic compounds like tryptamines can exert their effects by two possible mechanisms: binding to the transmembrane serotonin receptor and/or modifying the properties of the neuronal membrane that can alter the conformational equilibrium and desensitize receptors. The impact of three different Tryptamine class compounds with a tertiary amine (dimethyltryptamine, bufotenine, and 5-MeO-DMT) in both neutral and charged forms on a model bilayer lipid membrane are studied using all-atom MD simulations. All compounds partition into the bilayer, and change membrane properties, but to different extents. We determine the tendency of compounds to partition into the membrane by free energy calculations. Neutral tryptamines partition into the bilayer almost completely. Dimethyltryptamine and 5-MeO-DMT cross the membrane spontaneously during the simulation time, but bufotenine does not, although it has the maximum effect on the structural properties of the membrane. However, protonated compounds partition partially into the bilayer and cannot pass through the middle of the membrane during the simulation time. In this way, subtle alteration of chemical structure can play a significant role in the improvement or deterioration of partitioning of these compounds into the bilayer and their passage across the membrane.
Revealing the presence of Tryptamine new psychoactive substances using fused "neutral loss" spectra derived from DART high-resolution mass spectra
Talanta 2022 Aug 15;246:123417.PMID:35576755DOI:10.1016/j.talanta.2022.123417.
A data fusion approach for the rapid extraction of core scaffold information that can be used to facilitate structure determination for new psychoactive substance (NPS) tryptamines is described. The method involves the screening of DART-HRMS data of new tryptamines against a partial least squares-discriminant analysis (PLS-DA) model that predicts the core Tryptamine structure class into which the compound can be grouped. The PLS-DA prediction model was created and trained using neutral loss spectra derived from collision-induced dissociation (CID) DART mass spectral analysis of 50 Tryptamine structures acquired at 60 V and 90 V, in which the sample groups were revealed by hierarchical clustering analysis (HCA). HCA of the fused neutral loss data clustered the 50 tryptamines into 10 groups based on the identities of the neutral fragments lost during fragmentation. "Leave-one-structure-out" validation of the PLS-DA model gave 100% accuracy, precision, sensitivity, and specificity. For external validation, the ability of the model to classify four compounds that were unfamiliar to it was tested, and the model was found to correctly predict the skeletal framework in each case. The results show proof of concept for how this approach can aide in the identification of new emerging psychoactive compounds.