Dimethoxy strychnine

Base Information

• Chemical Name: Dimethoxy strychnine
• CAS No.: 357-57-3
• Molecular Formula: C23H26 N2 O4
• Molecular Weight: 394.47
• Hs Code.: 29399900
• NSC Number: 757797
• Wikidata: Q27163515
• ChEMBL ID: CHEMBL3039186
• Mol file: 357-57-3.mol

Synonyms:Brucine alkaloid;Dimethoxy strychnine;2,3-Dimethoxy-strychnine;RCRA waste no. P018;RCRA waste number P018;SR-05000001553;Strychnine, 2,3-dimethoxy-;Strychnidin-10-one, 2,3-dimethoxy-;dimethoxystrychnine;Spectrum_001121;SpecPlus_000567;Spectrum2_000564;Spectrum3_000624;Spectrum4_001882;Spectrum5_000504;BSPBio_002188;KBioGR_002408;KBioSS_001601;DivK1c_006663;SPECTRUM1500822;SPBio_000348;SCHEMBL1648976;Brucine [UN1570] [Poison];CHEMBL3039186;CHEBI:91694;KBio1_001607;KBio2_001601;KBio2_004169;KBio2_006737;KBio3_001688;C24H28N2O4;HMS1921K04;HMS2092M06;Pharmakon1600-01500822;CCG-38730;NSC757797;AKOS015895960;LS-1234;SDCCGMLS-0066964.P001;SBI-0052330.P002;AB00052839_02;AB00052839_03;SR-05000001553-1;SR-05000001553-2;BRD-A41995253-001-02-9;Q27163515;(4aR,5aS,8aR,15bR)-10,11-dimethoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one

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Chemical Property of Dimethoxy strychnine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 5.76E-16mmHg at 25°C
• Melting Point: 175-178 ºC (dec.)
• Refractive Index: 1.685
• Boiling Point: 633.7 °C at 760 mmHg
• PKA: 8.28(at 25℃)
• Flash Point: 337.1 °C
• PSA: 51.24000
• Density: 1.41 g/cm³
• LogP: 2.11260
• Storage Temp.: Store at RT
• Water Solubility.: Soluble in alcohol, chloroform, and benzene, slightly soluble in water, ether, and glycerol
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 394.18925731
• Heavy Atom Count: 29
• Complexity: 785

Purity/Quality:

Safty Information:

• Hazard Codes: T+
• Statements: 26/28-52/53
• Safety Statements: 13-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C34CCN5C3CC6C7C4N2C(=O)CC7OCC=C6C5)OC
• Isomeric SMILES: COC1=C(C=C2C(=C1)[C@]34CCN5[C@H]3C[C@@H]6[C@@H]7C4N2C(=O)CC7OCC=C6C5)OC
• Description: As a Chinese medicine, brucine was firstly recorded in Compendium of Materia Medica. The Chinese name for brucine is “Maqian” because it looks like ancient coins with horse icon, where “Ma” refers to “horse” and “qian” refers to “coins.” This traditional Chinese herb has cold, bitter, and toxic properties. It can be used to treat typhoid fever, throat pain, and lumps. Brucine is mainly extracted from the traditional Chinese medicine “Maqian.” In 1819, Pelletier and Caventou firstly isolated the alkaline brucine from the seeds and bark of Strychnos nux-vomica L.?Brucine is the dry and mature seeds of Loganiaceae Evergreen tree plants including Strychnos nux-vomica L. and Strychnos pierriana A.W. Hill.
• Physical properties: Appearance: white crystalline powder; tastes very bitter. Solubility: slightly soluble in water; soluble in ether, chloroform, ethanol, methanol, and other organic solvents . Melting point: 175–178?°C. Specific optical rotation: ?118°.
• Uses: Brucine is used as a denaturing alcohol, lubricant additive, separation of racemic mixtures. Proposed to reduce inflammatory mediators including COX-2, PGE2 and thromboxane B2. Able to induce cell apoptosis, with cytotoxic and antiproliferative effects. Brucine occurs in the seeds of strychnosspecies (Strychnos nux vomica L. and otherspecies). It is used for denaturing alcoholsand oils; for separating racemic mixtures;and as an additive to lubricants. It is alsoused for colorimetric analysis of nitrate.Therapeutically, it is used as a stimulant. 10,11-Dimethoxystrychnine can be used for antineoplastic, convulsant.
• Clinical Use: The applications of brucine include reducing swelling; resolving mass; activating meridians to stop pain; attenuating rheumatism, stubborn paralysis, and numbness paralysis; alleviating bruises; etc. It has been used for nearly a thousand years and achieved prominent clinical efficacy. In the clinical practice, brucine is used as a compatibility prescription or compound medicine in treating rheumatism, rheumatoid arthritis, stroke hemiplegia, dementia, retinopathy, and orthopedic and other surgical diseases.Brucine is the main active ingredient in Strychnos and plays an important role in treating diseases. However, brucine is also a toxic ingredient, which limits the scope of its clinical application. Further studies of its pharmacological effects and toxicity will improve its clinical application.

Technology Process of Dimethoxy strychnine

There total 12 articles about Dimethoxy strychnine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

brucine N-oxide (17301-81-4) → brucine (357-57-3)

Guidance literature:

With niobium pentachloride; zinc; In tetrahydrofuran; benzene; at 23 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2009.02.013

Reference yield: 84.0%

1:1 complex of 3-phenylhepta-1-yn-3-ol and brucine → brucine (357-57-3)

Guidance literature:

With hydrogenchloride; In benzene;

DOI:10.1246/cl.1988.1755

Reference yield:

2,3-dihydroxy-19α-oxy-strychnidin-10-one (19879-79-9) → brucine (357-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH

2: H₂SO₃

With sodium hydroxide; sulphurous acid;

upstream raw materials:

diazomethane

10-hydroxystrychnine

brucine N-oxide

9,10-seco-strychnidin-10-oic acid

Downstream raw materials:

10,11-dihydroxystrychnine

Isobrucine

brucine N-oxide

brucidine