Thiocolchicine

Suppliers

Names

[ Name ]:
Thiocolchicine

[Synonym ]:
thiocolhicine
N-[(7S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
10-Demethoxy-10-methylthiocolchicine
N-((S)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide
Thiocolchicine
thiocolchicine
EINECS 220-346-8
Colchicine,10-thio
N-((S)-1,2,3-Trimethoxy-10-methylmercapto-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamid
Thiocholchicine
Colchicine,10-demethoxy-10-(methylthio)

Chemical & Physical Properties

[ Density]:
1.27g/cm3

[ Boiling Point ]:
729.1ºC at 760mmHg

[ Molecular Formula ]:
C₂₂H₂₅NO₅S

[ Molecular Weight ]:
415.50300

[ Flash Point ]:
394.7ºC

[ Exact Mass ]:
415.14500

[ PSA ]:
99.16000

[ LogP ]:
3.97580

[ Vapour Pressure ]:
4.12E-21mmHg at 25°C

[ Index of Refraction ]:
1.609

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GH0878800

CHEMICAL NAME :: Colchicine, 10-demethoxy-10-methylthio-

CAS REGISTRY NUMBER :: 2730-71-4

LAST UPDATED :: 199409

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H25-N-O5-S

MOLECULAR WEIGHT :: 415.54

WISWESSER LINE NOTATION :: L B677 MV&T&J CO1 DO1 EO1 JMV1 NS1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 997 ug/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 24,636,1981

Safety Information

[ Symbol ]:

GHS05, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300 + H330-H318-H340

[ Precautionary Statements ]:
P201-P260-P264-P280-P284-P301 + P310

[ Hazard Codes ]:
T+

[ RIDADR ]:
UN 1544PSN1 6.1 / PGI

Precursor & DownStream

Precursor

Colchicine
Sodium thiomethoxide
Methyl mercaptan
Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)-
Ethanoic anhydride
N-(1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl)acetamide
diazomethane

DownStream

Acetamide,N-[(7S)-5,6,7,9-tetrahydro-1,2,3-trimethoxy-10-(methylsulfonyl)-9-oxobenzo[a]heptalen-7-yl]-
Benzo[a]heptalen-9(5H)-one,7-amino-6,7-dihydro-1,2,3-trimethoxy-10-(methylthio)-, (7S)-
3-demethylthiocolchicine
N-(1,2,3-trimethoxy-10-methylsulfinyl-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl)acetamide
Thiocolchicine analog
2,3-didemethylthiocolchicine
10-demethoxy-1-O,2-O-didemethyl-10-(methylthio)colchicine

Articles

Antiproliferative activity of colchicine analogues on MDR-positive and MDR-negative human cancer cell lines.

Anticancer Drug Des. 13 , 19-33, (1998)

In this study the in vitro antitumor activity of a series of 20 colchicine analogues was tested and compared with colchicine and thiocolchicine on three different human cancer cell lines, two of which...

Antitumor agents--CLXXV. Anti-tubulin action of (+)-thiocolchicine prepared by partial synthesis.

Bioorg. Med. Chem. 5(12) , 2277-82, (1997)

(+)-Thiocolchicine (2b) was prepared from (+/-)-colchicine (1) in a five-step reaction sequence that included chromatographic separation of appropriate camphanylated diastereomers. Acid hydrolysis of ...

Thiocolchicine dimers: a novel class of topoisomerase-I inhibitors.

Biochem. Pharmacol. 69(1) , 113-21, (2005)

During a cellular screening of thiocolchicine analogs, thiocolchicine dimers resulted particularly active in cisplatin-resistant A2780-CIS cells. In order to discover by which mechanism(s) thiocolchic...