3,4-Dimethoxyphenethylamine
(Synonyms: 3,4-二甲氧基苯乙胺) 目录号 : GC39777
An Analytical Reference Standard
Cas No.:120-20-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3,4-Dimethoxyphenethylamine (hydrochloride) is an analytical reference standard that is structurally categorized as a phenethylamine. It inhibits the deamination of tyramine and tryptamine by rat brain monoamine oxidase.1 This product is intended for research and forensic applications.
1.Keller, W.J., and Ferguson, G.G.Effects of 3,4-dimethoxyphenethylamine derivatives on monoamine oxidaseJ. Pharm. Sci.66(7)1048-1050(1977)
| Cas No. | 120-20-7 | SDF | |
| 别名 | 3,4-二甲氧基苯乙胺 | ||
| Canonical SMILES | NCCC1=CC=C(OC)C(OC)=C1 | ||
| 分子式 | C10H15NO2 | 分子量 | 181.23 |
| 溶解度 | Soluble in DMSO | 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 | 5.5179 mL | 27.5893 mL | 55.1785 mL |
| 5 mM | 1.1036 mL | 5.5179 mL | 11.0357 mL |
| 10 mM | 0.5518 mL | 2.7589 mL | 5.5179 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。
Effects of 3,4-Dimethoxyphenethylamine derivatives on monoamine oxidase
J Pharm Sci 1977 Jul;66(7):1048-50.PMID:886445DOI:10.1002/jps.2600660741.
The cactus alkaloid 3,4-Dimethoxyphenethylamine and its naturally occurring N-methylated homologs inhibited the deamination of tyramine and tryptamine by rat brain monoamine oxidase. In contrast, the beta-hydroxylated derivatives of this series failed to inhibit the action of monoamine oxidase on both tyramine and tryptamine.
MDA, MDMA, and other "mescaline-like" substances in the US military's search for a truth drug (1940s to 1960s)
Drug Test Anal 2018 Jan;10(1):72-80.PMID:28851034DOI:10.1002/dta.2292.
This article describes the context in which 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxymethamphetamine (MDMA) and other mescaline-like compounds were explored as hallucinogens for military and intelligence purposes from the 1940s to the 1960s. Germans first tested mescaline as a "truth drug" in a military context. In the 1940s, the United States military started testing hallucinogenic substances as truth drugs for interrogation and behavior manipulation. After tests carried out using mescaline and other drugs in 1950, some derivatives of mescaline were synthesized by the Army for the exploration of possible "speech-inducing" effects. After insufficient animal testing, the substances were given to patients at the New York State Psychiatric Institute (NYSPI). 3,4-Methylenedioxy-N-ethylamphetamine (MDE), a compound almost identical to MDMA, was among the compounds delivered for testing at the NYSPI. During tests with other derivatives (3,4-Dimethoxyphenethylamine (DMA), 3,4-methylenedioxyphenethylamine (MDPEA), MDA) in 1952-53, an unwitting patient died in these tests, which was kept secret from the public. Research was interrupted and toxicological animal testing procedures were initiated. The secret animal studies run in 1953/1954 revealed that some of the "mescaline derivatives" tested (e.g. MDA, MDE, DMA, 3,4,5-trimethoxyamphetamine (TMA), MDMA) were considered for further testing in humans. In 1955, the military changed focus to lysergic acid diethylamide (LSD), but some interest in mescaline-like compounds remained for their ability to change mood and habit without interfering with cognition and sensory perception. Based on the known documents, it remains unclear (but probable) whether any of the mescaline derivatives tested were being used operationally.
Synthesis of a series of 3-cyanopropionamides and 4-imino-gamma-butyrolactams and evaluation of their function as modulators of multidrug resistance
Arch Pharm (Weinheim) 2000 Oct;333(10):329-36.PMID:11092135DOI:10.1002/1521-4184(200010)333:10<329::aid-ardp329>3.0.co;2-6.
The synthesis of the 3-cyanopropionamides 3a and 3b, of the 2,2-dimethyl-3-cyanopropionamides 4a-4c and of the 4-imino-gamma-butyrolactams 5a and 5b (cyclic functional isomers of 3-cyanopropionamides) is described. The amides 3a and 3b were obtained by aminolysis of the corresponding acid chlorides, which are accessible via hydrolysis of the ethyl esters to the acids. This methodology was not used for the synthesis of the amides 4a-4c owing to steric hindrance to hydrolysis in the corresponding ethyl esters. These nonreactive esters, accessible by alkylation of 1-cyano carbanions with ethyl bromodimethylacetate, could be directly converted into the amides 4a-4c by aminolysis with the lithium amide of 3,4-dimethoxy-N-methylphenethylamine. Instead of open-chain amides, the lactams 5a and 5b are obtained when the lithium amide of 3,4-Dimethoxyphenethylamine (i.e., of a primary rather than secondary amine) is used for the aminolysis. The synthesized compounds were tested for their ability to decrease the resistance to vincristine in a multidrug-resistant subline of murine leukemic lymphoblasts that are 300-fold resistant to the antiproliferative drug. The amides 4a and 4c, and lactam 5a, all of which have a highly branched carbon backbone, were active. Lactam 5a reduced the vincristine resistance by 90% at a 2-microM concentration.
Synthesis of novel sulfonamides with anti-Alzheimer and antioxidant capacities
Arch Pharm (Weinheim) 2021 Jul;354(7):e2000496.PMID:33749025DOI:10.1002/ardp.202000496.
A series of novel dopamine analogs incorporating urea and sulfonamide functional groups was synthesized from 3,4-Dimethoxyphenethylamine. The reaction of 3,4-Dimethoxyphenethylamine with N,N-dimethylcarbamoyl chloride, followed by the sulfonyl chlorination of the urea derivative, gave benzene-1-sulfonyl chloride 9, which was reacted with NH3 (aq) or N-alkyl amines to give related sulfonamides. The O-demethylation reaction of the subsequent compounds with BBr3 afforded four novel phenolic dopamine analogs including sulfonamide and urea in the same structure. The anticholinergic and antioxidant effects of the synthesized compounds were examined. Compound 13 exhibited inhibition at the micromolar level for both acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The IC50 value of 13 was calculated as 298 ± 43 µM for AChE and 321 ± 29 µM for BChE. The antioxidant and antiradical effects of the molecules were investigated by five different methods. Among the synthesized compounds 10-18, the best antioxidant and antiradical activities belong to the phenolic compounds 15-18. Compounds 16 and 18 have a higher reducing power than the standards used, that is, butylated hydroxytoluene, butylated hydroxyanisole, Trolox, and α-tocopherol, for Fe3+ -Fe2+ and Cu2+ -Cu+ reducing activities. For the DPPH• radical scavenging method, compounds 16-18 have a much better scavenging power than the standard molecules. In addition, it has been determined by the induced-fit docking method that compound 13 is well-fitted in the active site of the enzymes. ADME studies reveal that the pharmacokinetic and physicochemical properties of all synthesized compounds are within an acceptable range.
Cactus alkaloids XXXIII: beta-phenethylamines from the Guatemalan cactus Pilosocereus maxonii
J Pharm Sci 1977 Oct;66(10):1485-7.PMID:925910DOI:10.1002/jps.2600661037.
TLC analysis of extracts of Pilosocereus maxonii (Rose) Byles and Rowley detected six identifiable alkaloids. Preparative TLC aided in the crystallization of the hydrochlorides of N-methyl-3,4-dimethoxyphenethylamine, N-methyl-3-methoxytyramine, and N,N-dimethyl-3-methoxytyramine. Traces of 3,4-Dimethoxyphenethylamine (TLC and mass spectrometry), tyramine (TLC), and N-methyltyramine (TLC) were identified. While all of these compounds were isolated and/or detected previously in other cactus species, this study is the first reported crystallization of N-methyl- and N,N-dimethyl-3-methoxytyramine from a natural source.