CAS Number64-86-8
SynonymsColchineos; (S)-colchicine; N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide; Colchicin; Condylon; EINECS 200-598-5; Colchicina; colchicinum; (1E)-N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]ethanimidic acid; Colcin; Colchisol; MFCD00078484; (-)-N-[(7S,12a5)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]-acetamide; Colchicine; (S)-N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl) acetamide; [3H]-Colchicine; Colsaloid
Molecular FormulaC22H25NO6
Molecular Weight399.44
Purity≥95 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point726.0±60.0 °C at 760 mmHg
Melting Point150-160 °C (dec.) (lit.)
Appearancepowder
EINECS200-598-5
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 64-86-8 |
| Catalog No. | 2A-9009900 |
| Chinese Name | 秋水仙碱 |
| Synonyms | Colchineos; (S)-colchicine; N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide; Colchicin; Condylon; EINECS 200-598-5; Colchicina; colchicinum; (1E)-N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]ethanimidic acid; Colcin; Colchisol; MFCD00078484; (-)-N-[(7S,12a5)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]-acetamide; Colchicine; (S)-N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl) acetamide; [3H]-Colchicine; Colsaloid |
| Molecular Formula | C22H25NO6 |
| Molecular Weight | 399.44 |
| Purity | ≥95 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 726.0±60.0 °C at 760 mmHg |
| Melting Point | 150-160 °C (dec.) (lit.) |
| Appearance | powder |
| Water Solubility | 45 g/L (20 ºC) |
| Storage Condition | Brown glass bottle with light-sealed packaging. St |
| Packaging | I |
| Application | Colchicine is a tubulin inhibitor and microtubule disruptor. Colchicine inhibits microtubule polymerization with an IC50 of 3 nM. |
| EINECS | 200-598-5 |
| PubChem ID | 24892656 |
| MDL Number | MFCD00078484 |
| SMILES | COC1=CC=C2C(=CC1=O)[C@H](CCc3cc(OC)c(OC)c(OC)c23)NC(C)=O |
| InChI | 1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1 |
| InChI Key | IAKHMKGGTNLKSZ-INIZCTEOSA-N |
| Beilstein/REAXYS | 2228813 |
| NACRES Code | NA.72 |
| UNSPSC | 10171502 |
| Hazard Symbols | 6.1 |
| MSDS | msds/9900_1_64_86_8.pdf |
| Bioactivity | Colchicine is a tubulin inhibitor and a microtubule disrupting agent. Colchicine inhibits microtubule polymerization with an IC50 of 3 nM. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Natural Products >> Alkaloid Research Areas >> Cancer Target Microtubule/Tubulin[1] In Vitro Exposure to 1μM Colchicine, a microtubule disrupting agent, triggered apoptosis in rat cerebellar granule cells (CGC). Colchicine treatment also causes alterations in Ca2+ responses to chemical depolarization and a moderate, but progressive, increase in the resting intracellular Ca2+ concentration[1]. Colchicine exerts its biological effects through binding to the soluble tubulin heterodimer, the major component of the microtubule. The Colchicine binding abilities of tubulins from a variety of sources are summarized, and the mechanism of Colchicine binding to brain tubulin is explored in depth. The relationship between colchicinoid structure and tubulin binding activity provides insight into the structural features of Colchicine responsible for high affinity binding to tubulin and is reviewed for analogs in the Colchicine series. The thermodynamic and kinetic aspects of the association are described and evaluated in terms of the binding mechanism. Colchicine binding to tubulin results in unusual alterations in the low energy electronic spectra of Colchicine. The spectroscopic features of Colchicine bound to tubulin are discussed in terms of the nature of the Colchicine-tubulin complex. Attempts to locate the high affinity Colchicine binding site on tubulin are presented[2]. Colchicine treatment inhibits indomethacin-induced small intestinal injury by 86% (1 mg/kg) and 94% (3 mg/kg) as indicated by the lesion index 24 h after indomethacin administration. Colchicine inhibits the protein expression of cleaved caspase-1 and mature IL-1β, without affecting the mRNA expression of NLRP3 and IL-1β[3]. In Vivo Vehicle or Colchicine (1 mg/kg) is administered orally 30 min prior to indomethacin administration. The lesions stained with Evans blue in the small intestine are smaller in Colchicine-treated mice than those in vehicle-treated mice 24 h after indomethacin administration. In addition, histological examination shows that Colchicine-treated mice have less mucosal inflammation and ulceration and a decrease in the size and numbers of lesions compared with vehicle-treated mice. Colchicine treatment significantly reduces the lesion index at doses of 1 mg/kg and 3 mg/kg (by 86% and 94%, respectively) compared with vehicle treatment. Colchicine treatment significantly inhibits the protein levels of mature IL-1β at doses of 1 mg/kg and 3 mg/kg (by 56% and 69%, respectively) without affecting those of pro-IL-1β. Colchicine treatment also significantly inhibits the protein levels of cleaved caspase-1 at doses of 1 mg/kg and 3 mg/kg (by 26% and 39%, respectively) without affecting those of pro-caspase-1[3]. Animal Admin Mice[3] Specific-pathogen-free 8-week-old male mice are used. Wild-type C57BL/6 mice and NLRP3−/− mice on a C57BL/6 background are used. To examine the effects of Colchicine on NSAID-induced small intestinal injury, vehicle or Colchicine (1 or 3 mg/kg) is administered orally 30 min prior to indomethacin administration. Mice received intraperitoneal injections of sterilized phosphate buffered saline or mouse recombinant IL-1β (0.1 μg/kg) 3 h after indomethacin treatment. Vehicle or Colchicine (1 or 3 mg/kg) is also administered to NLRP3−/− mice before indomethacin administration. The lesion index is evaluated 24 h after indomethacin administration, and examined mRNA and protein expression of inflammasome components 6 h after indomethacin administration. References [1]. Bonfoco E, et al. Colchicine induces apoptosis in cerebellar granule cells. Exp Cell Res. 1995 May;218(1):189-200. [2]. Hastie SB. Interactions of colchicine with tubulin. Pharmacol Ther. 1991;51(3):377-401 [3]. Otani K, et al. Colchicine prevents NSAID-induced small intestinal injury by inhibiting activation of the NLRP3 inflammasome. Sci Rep. 2016 Sep 2;6:32587. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 726.0±60.0 °C at 760 mmHg Melting Point 150-160 °C (dec.)(lit.) Molecular Formula C22H25NO6 Molecular Weight 399.437 Flash Point 392.9±32.9 °C Exact Mass 399.168182 PSA 83.09000 LogP 0.92 Vapour Pressure 0.0±2.4 mmHg at 25°C Index of Refraction 1.585 InChIKey IAKHMKGGTNLKSZ-INIZCTEOSA-N SMILES COc1cc2c(c(OC)c1OC)-c1ccc(OC)c(=O)cc1C(NC(C)=O)CC2 Water Solubility 45 g/L (20 ºC) |
| Use of | Colchicine is a tubulin inhibitor and a microtubule disrupting agent. Colchicine inhibits microtubule polymerization with an IC50 of 3 nM. Properties Articles340 Name N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide Synonym More Synonyms Colchicine Biological Activity Description Colchicine is a tubulin inhibitor and a microtubule disrupting agent. Colchicine inhibits microtubule polymerization with an IC50 of 3 nM. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Natural Products >> Alkaloid Research Areas >> Cancer Microtubule/Tubulin[1] References [1]. Bonfoco E, et al. Colchicine induces apoptosis in cerebellar granule cells. Exp Cell Res. 1995 May;218(1):189-200. [2]. Hastie SB. Interactions of colchicine with tubulin. Pharmacol Ther. 1991;51(3):377-401 [3]. Otani K, et al. Colchicine prevents NSAID-induced small intestinal injury by inhibiting activation of the NLRP3 inflammasome. Sci Rep. 2016 Sep 2;6:32587. Chemical & Physical Properties Molecular Formula C22H25NO6 Exact Mass 399.168182 PSA 83.09000 Index of Refraction 1.585 InChIKey IAKHMKGGTNLKSZ-INIZCTEOSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Danger Regulations: 1544 International Maritime Transport Danger Regulations: 1544 International Air Transport Danger Regulations: 1544 14.2 United Nations shipping name European Land Transport Dangerous Regulations: ALKALOIDS, SOLID, N.O.S. (Colchicine) IMDG Code: ALKALOIDS, SOLID, N.O.S. (Colchicine) IMDG: Alkaloids, solid, n.o.s. (Colchicine) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Dangerous Regulations for land transport: I International Dangerous Regulations for sea transport: I International Dangerous Regulations for air transport: I 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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