76-75-5 Usage
Chemical Properties
Off-White Solid
Originator
Pentothal,Abbott
Uses
A thio-derivative of Barbituric acid. Controlled substance (depressant). Anesthetic
Manufacturing Process
130 g of ethyl (1-methylbutyl) malonic ester is added to a concentrated
solution of sodium ethylate prepared from 34 g of sodium in absolute alcohol;
with stirring, 60 g of finely divided thiourea is added, and, the mixture
refluxed for 10 hours. Most or all of the solvent is evaporated and the residual
mass is dissolved in cold water. The barbituric acid derivative so formed is
precipitated by the addition of dilute hydrochloric acid. It may be 1 purified by
solution in dilute ammonium hydroxide solution and precipitated by carbon
dioxide, followed by recrystallization from 95% alcohol. The ethyl (1-
methylbutyl)thiobarbituric acid so obtained is a white crystalline solid, melting
at 158-159°C and readily forming salts with alkalies.
Therapeutic Function
Narcotic analgesic, Anesthetic
Safety Profile
Poison by intraperitoneal, intravenous, and rectal routes. Moderately toxic by ingestion. An experimental teratogen. Human mutation data reported. A short-acting intravenous anesthetic. When heated to decomposition it emits very toxic fumes of NOx and SOx
Check Digit Verification of cas no
The CAS Registry Mumber 76-75-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 6 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 76-75:
(4*7)+(3*6)+(2*7)+(1*5)=65
65 % 10 = 5
So 76-75-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H18N2O2S/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
76-75-5Relevant articles and documents
Barbiturates bind in the GLIC ion channel pore and cause inhibition by stabilizing a closed state
Fourati, Zaineb,Ruza, Reinis Reinholds,Laverty, Duncan,Drège, Emmanuelle,Delarue-Cochin, Sandrine,Joseph, Delphine,Koehl, Patrice,Smart, Trevor,Delarue, Marc
, p. 1550 - 1558 (2017/02/10)
Barbiturates induce anesthesia by modulating the activity of anionic and cationic pentameric ligand-gated ion channels (pLGICs). Despite more than a century of use in clinical practice, the prototypic binding site for this class of drugs within pLGICs is yet to be described. In this study, we present the first X-ray structures of barbiturates bound to GLIC, a cationic prokaryotic pLGIC with excellent structural homology to other relevant channels sensitive to general anesthetics and, as shown here, to barbiturates, at clinically relevant concentrations. Several derivatives of barbiturates containing anomalous scatterers were synthesized, and these derivatives helped us unambiguously identify a unique barbiturate binding site within the central ion channel pore in a closed conformation. In addition, docking calculations around the observed binding site for all three states of the receptor, including a model of the desensitized state, showed that barbiturates preferentially stabilize the closed state. The identification of this pore binding site sheds light on the mechanism of barbiturate inhibition of cationic pLGICs and allows the rationalization of several structural and functional features previously observed for barbiturates.
Solubility profiles for several barbiturates in hydroalcoholic mixtures.
Breon,Paruta
, p. 1306 - 1313 (2007/10/04)
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