3,4,5-Trimethoxyphenylacetic acid
目录号 : GC680823,4,5-Trimethoxyphenylacetic acid 是 Mescaline 的代谢物。
Cas No.:951-82-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3,4,5-Trimethoxyphenylacetic acid is a metabolite of Mescaline[1].
[1]. Demisch L, et al. 3,4,5-Trimethoxybenzoic acid, a new mescaline metabolite in humans. Drug Metab Dispos. 1978 Sep-Oct;6(5):507-9.
| Cas No. | 951-82-6 | SDF | Download SDF |
| 分子式 | C11H14O5 | 分子量 | 226.23 |
| 溶解度 | DMSO : ≥ 100 mg/mL (442.03 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 | 4.4203 mL | 22.1014 mL | 44.2028 mL |
| 5 mM | 0.8841 mL | 4.4203 mL | 8.8406 mL |
| 10 mM | 0.442 mL | 2.2101 mL | 4.4203 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。
Bacterial degradation of 3,4,5-trimethoxyphenylacetic and 3-ketoglutaric acids
J Bacteriol 1981 Aug;147(2):477-81.PMID:7263613DOI:10.1128/jb.147.2.477-481.1981.
When grown at the expense of 3,4,5-Trimethoxyphenylacetic acid, a species of Arthrobacter readily oxidized 3,4-dihydroxy-5-methoxyphenylacetic acid, but other structurally related aromatic acids were oxidized only slowly. Cell extracts contained a dioxygenase for 3,4-dihydroxy-5-methoxyphenylacetate, and the corresponding trihydroxy acid, which was not attacked by the enzyme, inhibited oxidation of this ring-fission substrate. Cell suspensions did not release carbon dioxide from 3,4-[methoxyl-14C]dihydroxy-5-methoxyphenylacetate but accumulated 1 mol of methanol per mol of 3,4,5-trimethoxyphenylacetate oxidized. A cell extract converted the ring-fission substrate into stoichiometric amounts of pyruvate and acetoacetate, formed from 3-ketoglutarate by the action of an induced decarboxylase. 3-Ketoglutaric acid served as sole source of carbon for many soil isolates.
3,4,5-Trimethoxybenzoic acid, a new mescaline metabolite in humans
Drug Metab Dispos 1978 Sep-Oct;6(5):507-9.PMID:30599doi
After ingestion of 400 mg of mescaline sulfate by human volunteers, 3,4,5-trimethoxybenzoic acid was isolated from urine and identified by gas chromatography-mass spectrometry. The amount of this anionic mescaline metabolite was found to be very low as compared with that of the well-konwn 3,4,5-Trimethoxyphenylacetic acid. The significance of this finding is discussed.
3,4,5-Trimethoxyphenylacetaldehyde, an intermediate metabolite of mescaline, is a substrate for microsomal aldehyde oxygenase in the mouse liver
Biol Pharm Bull 1995 May;18(5):696-9.PMID:7492985DOI:10.1248/bpb.18.696.
3,4,5-Trimethoxyphenylacetaldehyde, an intermediate metabolite of mescaline, was oxidized to 3,4,5-Trimethoxyphenylacetic acid by mouse hepatic microsomes. The reaction was NADPH-dependent, and inhibited by SKF 525-A, metyrapone and disulfiram. A P450 isozyme in mouse hepatic microsomes, P450 MUT-2 (CYP2C29), catalyzed the reaction (0.96 nmol/min/nmol P450) in which NADPH and NADPH-cytochrome c reductase were essential for the catalytic activity. The reaction was confirmed to be an oxygenation since molecular oxygen was incorporated into the carboxylic acid metabolite formed under oxygen-18 gas by GC-MS analysis. By addition of antibody against CYP2C29 to the microsomes (3.2 mg/mg microsomal protein) the MALDO activity was inhibited by 35% of the control value with preimmune serum, suggesting that CYP2C29 or an immunologically-related isozyme(s) plays a major role in the NADPH-dependent oxidation of 3,4,5-trimethoxyphenylacetaldehyde to 3,4,5-Trimethoxyphenylacetic acid by mouse hepatic microsomes. Pharmacological experiments on mescaline and its deaminated metabolites using mice indicated that the metabolites were much less active or were inactive in cataleptogenic effect and pentobarbital-induced sleep prolongation as compared with the parent compound.
Development and validation of an LC-MS/MS method for the quantification of mescaline and major metabolites in human plasma
J Pharm Biomed Anal 2022 Oct 25;220:114980.PMID:35963018DOI:10.1016/j.jpba.2022.114980.
Mescaline is a psychedelic phenethylamine found in different species of cacti. Currently, mescaline's acute subjective effects and pharmacokinetics are investigated in several modern clinical studies. Therefore, we developed a bioanalytical method for the rapid quantification of mescaline and its metabolites in human plasma. Mescaline and its metabolites 3,4,5-Trimethoxyphenylacetic acid (TMPAA), N-acetyl mescaline (NAM), and 3,5-dimethoxy-4-hydroxyphenethylamine (4-desmethyl mescaline) were simultaneously analyzed by ultra-high performance liquid chromatography tandem mass spectrometry (LC-MS/MS). Optimal chromatographic separation was achieved with an Acquity Premier HSS T3 C18 column. The analytes were detected in positive ionization mode using scheduled multiple reaction monitoring. A single step extraction method was implemented to enable fast and automatable plasma sample preparation. An intra-assay accuracy between 84.9% and 106% and a precision of ≤ 7.33% was observed in three validation runs. Plasma was extracted by simple protein precipitation, resulting in a complete recovery (≥ 98.3%) and minor matrix effects (≤ 7.58%). No interference with endogenous matrix components could be detected in human plasma samples (n = 7). Importantly, method sensitivity sufficed for assessing pharmacokinetic parameters of mescaline in clinical study samples with lower limits of quantification of 12.5, 12.5, and 1.25 ng/mL for mescaline, TMPAA, and NAM, respectively. Nonetheless, 4-desmethyl mescaline could not be selectively quantified in pharmacokinetic samples due to interference with another mescaline metabolite. Overall, we developed and validated a reliable and very easy-to-use method for forensic applications as well as investigating the clinical pharmacokinetics of mescaline.
Hapten-immunological studies on mescaline
Psychopharmacologia 1975;41(3):301-4.PMID:807928DOI:10.1007/BF00428941.
Antibodies with mescaline binding specificity were raised in rabbits by immunization with conjugates of bovine serum albumin with mescaline or its analogue 3,4,5-Trimethoxyphenylacetic acid. Immunized rats were given mescaline and their behavior was compared to that of non-immunized controls.