Thiamylal

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Structural formula
Structure of thiamylal
Structural formula without stereochemistry
General
Non-proprietary name Thiamylal
other names
  • ( RS ) -dihydro-5- (1-methylbutyl) -5- (2-propenyl) -2-thioxo-(1 H , 5 H ) -pyrimidine-4,6-dione
  • (±) -dihydro-5- (1-methylbutyl) -5- (2-propenyl) -2-thioxo-(1 H , 5 H ) -pyrimidine-4,6-dione
  • rac -dihydro-5- (1-methylbutyl) -5- (2-propenyl) -2-thioxo-(1 H , 5 H ) -pyrimidine-4,6-dione
  • DL -dihydro-5- (1-methylbutyl) -5- (2-propenyl) -2-thioxo-(1 H , 5 H ) -pyrimidine-4,6-dione
Molecular formula C 12 H 18 N 2 O 2 S
External identifiers / databases
CAS number 77-27-0
EC number 201-018-3
ECHA InfoCard 100,000,927
PubChem 3032285
ChemSpider 2297298
DrugBank DB01154
Wikidata Q906102
Drug information
ATC code

Q N01AF90

Drug class

sedative

properties
Molar mass 254.35 g · mol -1
Physical state

firmly

Melting point

132-133 ° C

pK s value

7.48

solubility

49.4 mg l −1 in water

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301-311-331
P: 261-280-301 + 310-311
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Thiamylal is a heterocyclic chemical compound from the group of barbiturates . The substance was developed in the 1950s and used as a medicinal substance with the trade name Surital . The barbituric acid derivative is a short-acting sedative with anticonvulsant and hypnotic properties. Thiamylal is still used in veterinary medicine to induce anesthesia, but no preparation is approved in Germany or Switzerland.

chemistry

Thiamylal is a pale yellow and hygroscopic powder with an unpleasant odor. When heated, the solution precipitates . In medicine, mainly thiamylal sodium ( CAS number 337-47-3, molar mass 276.33 g / mol) is used. The pH value of a 5% solution is strongly alkaline (10.5–11.5).

pharmacology

Thiamylal nonselectively suppresses the central nervous system and can cause different moods from mild excitement to mild sedation and sleep to deep coma or even death. Only in higher doses does it induce pain relief ( analgesia ).

The effect of thiamylal is similar to that of thiopental . As with all barbiturates, the release of acetylcholine , norepinephrine and glutamate is hindered. The sedative effect is triggered by the GABA A receptor , which activates the chloride channels and thus increases the neuronal chloride conductivity.

The LD 50 when administered intravenously to rats is 51 mg / kg.

Legal status

In the Federal Republic of Germany, thiamylal is a marketable and prescription narcotic drug due to its listing in Appendix 3 BtMG. Handling without permission or prescription is generally punishable. Further information can be found in the main article Narcotics Law in Germany .

Internationally, thiamylal falls under the Convention on Psychotropic Substances .

Use in food-producing animals is permitted, as thiamylal is listed in Table 1 (Permissible Substances) of the Annex to Regulation (EU) No. 37/2010. However, there is currently no approved preparation in Germany that contains the active ingredient thiamylal.

Web links

Individual evidence

  1. a b c Entry on thiamylal in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  2. a b Data sheet Thiamylal from Sigma-Aldrich , accessed on October 16, 2016 ( PDF ).
  3. Regulation (EU) No. 37/2010 (PDF) .