(-)-Demecolcine

Names

[ CAS No. ]:
477-30-5

[ Name ]:
(-)-Demecolcine

[Synonym ]:
Benzo[a]heptalen-9(5H)-one, 6,7-dihydro-1,2,3,10-tetramethoxy-7-(methylamino)-, (7S)-
Benzo[a]heptalen-9(5H)-one, 6,7-dihydro-1,2,3,10-tetramethoxy-7-(methylamino)-, (S)-
Demecolcine
Benzo(a)heptalen-9(5H)-one, 6,7-dihydro-1,2,3,10-tetramethoxy-7-(methylamino)-, (S)-
(7S)-1,2,3,10-Tetramethoxy-7-(methylamino)-6,7-dihydrobenzo[a]heptalen-9(5H)-one
demecolcinum
Colcemid
EINECS 207-514-6
demecolcina
N-Deacetyl-N-methylcolchicine
MFCD00075459

Biological Activity

[Description]:

Colcemid (Demecolcine), a derivative of colchicine, is a potent mitotic inhibitor[1][2]. Colcemid binds to the protein tubulin and arrest cells in metaphase for karyotyping assays. Colcemid incuces cell apoptosis and can be used for cancer research[2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[References]

[1]. T Tsuchida, et al. Colcemid-induced apoptosis of cultured human glioma: electron microscopic and confocal laser microscopic observation of cells sorted in different phases of cell cycle. Cytometry. 1998 Apr 1;31(4):295-9.

[2]. Ashley M Rozario, et al. Ultra-Low Colcemid Doses Induce Microtubule Dysfunction as Revealed by Super-Resolution Microscopy. Bioexiv.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
625.5±55.0 °C at 760 mmHg

[ Melting Point ]:
73-75ºC

[ Molecular Formula ]:
C₂₁H₂₅NO₅

[ Molecular Weight ]:
371.427

[ Flash Point ]:
332.1±31.5 °C

[ Exact Mass ]:
371.173279

[ PSA ]:
66.02000

[ LogP ]:
1.52

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.582

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GH0800000

CHEMICAL NAME :: Colchicine, N-deacetyl-N-methyl-

CAS REGISTRY NUMBER :: 477-30-5

BEILSTEIN REFERENCE NO. :: 2822892

LAST UPDATED :: 199801

DATA ITEMS CITED :: 49

MOLECULAR FORMULA :: C21-H25-N-O5

MOLECULAR WEIGHT :: 371.47

WISWESSER LINE NOTATION :: L B677 MV&T&J CO1 DO1 EO1 JM1 NO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 200 ug/kg

TOXIC EFFECTS :: Skin and Appendages - hair

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1700 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1700 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25530 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 35 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 87 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 3 mg/kg

SEX/DURATION :: female 7-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1800 ug/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - body wall

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1800 ug/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 500 ug/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 2500 ug/kg

SEX/DURATION :: female 2-26 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Sperm Morphology

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sex chromosome loss and nondisjunction

MUTATION DATA

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TEST SYSTEM :: Mammal - species unspecified

DOSE/DURATION :: 2 ug/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 201,423,1988 *** REVIEWS *** TOXICOLOGY REVIEW JAMAAP JAMA, Journal of the American Medical Association. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1883- Volume(issue)/page/year: 172,1765,1960 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3189 No. of Facilities: 105 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 412 (estimated) No. of Female Employees: 287 (estimated)

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
22-24/25-45-36/37/39

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ RTECS ]:
GH0800000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Precursor & DownStream

Precursor

DownStream

Articles

Determination of colchicine and O-demethylated metabolites in decomposed skeletal tissues by microwave assisted extraction, microplate solid phase extraction and ultra-high performance liquid chromatography (MAE-MPSPE-UHPLC).

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 960 , 145-50, (2014)

Microwave assisted extraction (MAE) followed by microplate solid phase extraction (MPSPE) coupled with ultra high performance liquid chromatography (UHPLC) for the semi-quantitative determination of c...

High-affinity accumulation of a maytansinoid in cells via weak tubulin interaction.

PLoS ONE 10(2) , e0117523, (2015)

The microtubule-targeting maytansinoids accumulate in cells and induce mitotic arrest at 250- to 1000-fold lower concentrations than those required for their association with tubulin or microtubules. ...

Differentiation of primordial germ cells from induced pluripotent stem cells of primary ovarian insufficiency.

Hum. Reprod. 30(3) , 737-48, (2015)

Can the induced pluripotent stem cells (iPSCs) derived from women with primary ovarian insufficiency (POI) differentiate into germ cells for potential disease modeling in vitro?The iPSC lines derived ...