Thiocolchicoside

Names

[ CAS No. ]:
602-41-5

[ Name ]:
Thiocolchicoside

[Synonym ]:
Thiocolchicoside
Acetamide, N-[(7S)-3-(β-D-glucopyranosyloxy)-5,6,7,9-tetrahydro-1,2-dimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]-
UNII:T1X8S697GT
Thiocolchicine Glycoside
N-[(7S)-3-(b-D-glucopyranosyloxy)-1,2-dimethoxy-10-(methylthio)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
R. 271
Coltramyl
Musco-ril
N-[(7S)-3-(β-D-Glucopyranosyloxy)-1,2-dimethoxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
3,10-Di(demethoxy)-3-glucosyloxy-10-methylthiocolchicine
10-Thiocolchicoside
Tiocolchicoside

Biological Activity

[Description]:

Thiocolchicoside is a competitive γ-aminobutyric acid type A (GABAA) receptor antagonist and glycine receptor agonist in the central nervous system. Thiocolchicoside is a semisynthetic sulfur derivative of colchicoside. Thiocolchicoside is a muscle relaxant and has anti-inflammatory, and analgesic properties[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[Target]

GABAA) receptor; glycine receptor[1]

[In Vitro]

Thiocolchicoside (0.001, 0.1, 1, 10, 100 μM) reduces the amplitude of eIPSCs in a concentration-dependent manner with this effect being significant at 0.1 μM and maximal at 10 μM[1].

[References]

[1]. Carta M, et al. The muscle relaxant thiocolchicoside is an antagonist of GAB_AA receptor function in the central nervous system. Neuropharmacology. 2006 Sep;51(4):805-15.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
929.6±65.0 °C at 760 mmHg

[ Melting Point ]:
190-198ºC

[ Molecular Formula ]:
C₂₇H₃₃NO₁₀S

[ Molecular Weight ]:
563.617

[ Flash Point ]:
516.0±34.3 °C

[ Exact Mass ]:
563.182495

[ PSA ]:
189.31000

[ LogP ]:
-1.23

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.657

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AC2976015

CHEMICAL NAME :: Acetamide, N-(3-(beta-D-glucopyranosyloxy)-5,6,7,9-tetrahydro-1, 2-dimethoxy-10-(methy lthio)- 9-oxobenzo(a)heptalen-7-yl)-, (S)-

CAS REGISTRY NUMBER :: 602-41-5

BEILSTEIN REFERENCE NO. :: 0072205

LAST UPDATED :: 199801

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C27-H33-N-O10-S

MOLECULAR WEIGHT :: 563.67

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - excitement

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 109,386,1957

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 27500 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - excitement

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 109,386,1957

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - excitement

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 109,386,1957

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 ug/kg

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

REFERENCE :: FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 15,533,1960

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 mg/kg

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

REFERENCE :: FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 15,533,1960

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P301 + P312 + P330-P305 + P351 + P338

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
AC2976015

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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