(10S)-3,4,5,14-tetramethoxy-10-(methylamino)tricyclo[9.5.0.0^{2,7}]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one

• ChemBase ID: 105430
• Molecular Formular: C21H25NO5
• Molecular Mass: 371.4269
• Monoisotopic Mass: 371.17327291
• SMILES: O=c1c(OC)ccc2c(c1)[C@@H](NC)CCc1c2c(OC)c(OC)c(OC)c1
• Canonical SMILES: CN[C@H]1CCc2c(c3c1cc(=O)c(cc3)OC)c(OC)c(c(c2)OC)OC
• InChI: InChI=1S/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3/t15-/m0/s1
• InChIKey: NNJPGOLRFBJNIW-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-3,4,5,14-tetramethoxy-10-(methylamino)tricyclo[9.5.0.0^{2,7}]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one; (10S)-3,4,5,14-tetramethoxy-10-(methylamino)tricyclo[9.5.0.0^2,^7]hexadeca-1(16),2,4,6,11,14-hexaen-13-one
• IUPAC Traditional name: colcemid
• Synonyms: Demecolcine solution; Demecolcine; N-Deacetyl-N-methylcolchicine; N-Methyl-N-Deacetylcolchicine; Colcemid; 6,7-Dihydro-1,2,3,10-Tetramethoxy-7-(Methylamino) Benzo (alpha) Heptalen-9(5H)-one; DEMECOLCINE; (S)-1,2,3,10-tetramethoxy-7-(methylamino)-6,7-dihydrobenzo[a]heptalen-9(5H)-one; (7S)-6,7-Dihydro-1,2,3,10-tetramethoxy-7-(methylamino)-benzo[a]heptalen-9(5H)-one; Deacetylmethylcolchicine; Colchamin; NSC 3096; Omain; Omaine; Reichstein's F; N-Desacetyl-N-methylcolchicine; Colcemid™ 溶液; N-脱乙酰-N-甲基秋水仙碱 溶液; 地美可辛 溶液; N-脱乙酰-N-甲基秋水仙碱; 地美可辛

Database IDs

• CAS Number: 477-30-5
• EC Number: 207-514-6
• MDL Number: MFCD00075459
• Beilstein Number: 2822892
• PubChem SID: 24856707; 162092344; 24894128; 24893569
• PubChem CID: 220401

CALCULATED PROPERTIES

• Acid pKa: 16.95793
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.1205513
• LogD (pH = 7.4): -0.17595741
• Log P: 2.0757225
• Molar Refractivity: 106.7064 cm^3
• Polarizability: 40.089058 Å^3
• Polar Surface Area: 66.02 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble10 mg/mL; Dichlormethane; DMSO; ethanol: soluble; Methanol
• Apperance: liquid; Yellow Solid
• Melting Point: 186°C; 73-75°C

Safety Information

• Storage Condition: 2-8°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: GH0800000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 1; 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2XE
• Risk Statements: 25; R:25
• Safety Statements: 22-24/25-45; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); ≥98.0% (sum of enantiomers, HPLC)
• Concentration: 10 μg/mL in HBSS
• Sterility: sterile-filtered
• Quality Level: GMP
• Empirical Formula (Hill Notation): C21H25NO5
• Classification: Rare Genuine Natural Compounds

DETAILS

MP Biomedicals - 02190195

Crystalline
Used to immobilize chromosomes by inactivating the spindle fiber mechanism during metaphase. Binds tubulin and interferes with microtubule-dependent cell functions.

Sigma Aldrich - D1925

Application
用于使细胞停留在四分体时期来实现细胞同步化。可用于不含动物成分的应用中。
法律信息
Colcemid 商标 Ciba-Geigy Corporation
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D1925.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - D7385

Biochem/physiol Actions
解聚微管；在四分体时期阻断有丝分裂。 常用于染色体核型分析与细胞周期研究，以增加停留在细胞周期特定阶段的有丝分裂细胞的产量。可采用多种途径达到该目的，其中最常用的便是使用如地美可辛之类的细胞周期同步化试剂。地美可辛能使有丝分裂细胞或 G1 和 S 期的同步化细胞停留在四分体时期，同时也不会对其生化反应造成明显影响。通常用地美可辛处理白细胞以使细胞停留在四分体时期。

Sigma Aldrich - 27645

Biochem/physiol Actions
Depolymerizes microtubules; blocks mitosis at metaphase. Often in karyotyping and cell cycle research it is desirable to increase the yield of mitotic cells in a particular phase of the cell cycle. This can be achieved in a variety of ways with the most popular being the use of a cell cycle synchronizing agent such as demecolcine. Demecolcine will arrest cells in metaphase with no remarkable effect on the biochemical events in mitotic cells or in synchronized G1 and S phase cells. White blood cells are often treated with demecolcine to arrest cells in metaphase.
Other Notes
Binds tubulin hence interfering with microtubule-dependent cell function1

Toronto Research Chemicals - D230785

An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pa

REFERENCES

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