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SML0954

Sigma-Aldrich

Thiocolchicine

≥97% (HPLC)

Synonym(s):

10-Demethoxy-10-(methylthio)colchicine, 10-Thio-colchicine, N-[(7S)-5,6,7,9-Tetrahydro-1,2,3-trimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]-acetamide, NSC 186301

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About This Item

Empirical Formula (Hill Notation):
C22H25NO5S
CAS Number:
2730-71-4
Molecular Weight:
415.50
EC Number:
220-346-8
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

InChI

1S/C22H25NO5S/c1-12(24)23-16-8-6-13-10-18(26-2)21(27-3)22(28-4)20(13)14-7-9-19(29-5)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1

InChI key

CMEGANPVAXDBPL-INIZCTEOSA-N

Biochem/physiol Actions

Thiocolchicine is an antimitotic alkaloid and apoptosis inducer that inhibits tubulin polymerization and microtubule assembly.

Signal Word

Danger

Hazard Statements

H300 + H330,H318,H340

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Muta. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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[TENS + mesotherapy association in the therapy of cervico-brachialgia: preliminary data].
S Palermo et al.
Minerva anestesiologica, 57(10), 1084-1085 (1991-10-01)
L Sun et al.
Journal of medicinal chemistry, 36(5), 544-551 (1993-03-05)
A series of novel thiocolchicine analogs, 5,6-dihydro-6(S)-(acyloxy)-and 5,6-dihydro-6(S)-[(aroyloxy)-methyl]-1,2,3-trimethoxy-9-(methylthi o)-8H- cyclohepta[a]naphthalen-8-ones, possessing a six-membered ring B, have been synthesized and evaluated for their cytotoxicity against various tumor cell lines, including solid tumor cell lines, and for their interaction with tubulin. The
Bin Wang et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 41(11), 1057-1063 (2007-02-01)
To search for colchicine derivatives which have high efficacy and low toxicity. Colchicine was firstly converted into thiocolchicine, and then it was hydrolyzed to get 7-(N-deacetylthiocolchicine). At last, 7-(N-deacetylthiocolchicine) was amidated to get the target compounds. The chemical structure of
Bruno Danieli et al.
Chemistry & biodiversity, 1(2), 327-345 (2006-12-29)
The bifunctional taxoid-colchicinoid hybrids 6-8 were synthesized and evaluated in assays of cytotoxicity and tubulin assembly/disassembly. All compounds showed a high degree of cytotoxicity, but, while 6 and 7 behaved as bifunctional tubulin binders not unlike an equimolecular mixture of
B Wolach et al.
European journal of clinical investigation, 22(9), 630-634 (1992-09-01)
Colchicine has been used in diverse clinical settings such as gout, familial Mediterranean fever, liver cirrhosis, Behcet's disease and pericarditis. It also has an antimitotic potential hitherto unexplored due to its narrow therapeutic toxic ratio. The aim of the present
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