57-33-0

Usage

Chemical Properties

A white or almost white, crystalline powder, hygroscopic.

Originator

Nembutal,Abbott,US

Uses

Different sources of media describe the Uses of 57-33-0 differently. You can refer to the following data:
1. Sedative, hypnoyic. Controlled substance (depressant).
2. Human Pentobarbital as sodium salt has been used as a sedative and hypnotic in the short-term management of insomnia. Pentobarbital sodium has also been used for premedication in anesthetic procedures. Pentobarbital is FDA-approved for the emergency control of certain acute convulsive episodes, e.g., those associated with status epilepticus, cholera, eclampsia, meningitis, tetanus, and toxic reactions to strychnine or local anesthetics. The other indications for pentobarbital include treatment of nonfatal submersion and traumatic/nontraumatic raised intracranial pressure. Animal Intraperitoneal (IP) injection of pentobarbital is used in experimental medicine as an anesthetic in small animals such as rat and mouse. Pentobarbital is an important drug for relieving convulsive seizures, especially when caused by strychnine.

Manufacturing Process

Sodium (9.6 parts) was dissolved in butanol (192 parts) and di-n-butyl ethyl 1-methyl-n-butylmalonate (62.8 parts) and urea (14.4 parts) were added to the warm solution with agitation. The mixture was then heated to reflux temperature in three quarters of an hour and maintained for 2 hours. The reaction mass was kept, water (150 parts) added, the aqueous portion separated, and the butanol layer extracted with water (3 x 50 parts). The combined aqueous extracts were then given 3 small extractions with benzene, the aqueous liquors separated, charcoaled, filtered and precipitated with concentrated hydrochloric acid (acid to congopaper). The solid was collected, washed with water, dissolved in N-sodium hydroxide and reprecipitated with carbon dioxide. On recrystallization, from aqueous alcohol, the pentobarbitone was obtained.

Brand name

Nembutal (Ovation).

Therapeutic Function

Hypnotic, Sedative

General Description

Crystalline granules or white powder. Used as an anesthetic and sedative.

Air & Water Reactions

Freely soluble in water. Aqueous solutions are unstable upon storage.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, intravenous, intraduodenal, intramuscular, intracerebral, parented, and rectal routes. An experimental teratogen. Other experimental reproductive effects. Human systemic effects by ingestion: wakefulness, change in motor activity, ataxia, and antipsychotic effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and Na2O.

Environmental Fate

Routes and Pathways Relevant Physicochemicals Properties Pentobarbital sodium, with a molecular weight of 248.3, consists of white, crystalline granules or white powder with a slight characteristic odor. The melting point equals 130 °C and respective vapor pressure is 3.02 × 1010 mmHg at 25 °C. Pentobarbital is very soluble in water (679 mg l1), freely soluble in alcohol, and practically insoluble in ether. pH of a 10% solution in water is between 9.8 and 11.0. Its dissociation constant (pK) and octanol/water partition coefficient (log Kow) are 7.88 and 2.10, respectively. Henry’s law constant is 8.5  108 Pa m3 mol1 at 25°C.Environmental Persistency Due to lack of hydrolyze-prone functional groups, pentobarbital is not expected to undergo hydrolysis in the environment. Also, pentobarbital does not contain chromophores to absorb wavelengths higher than 290 nm and therefore is not susceptible to direct photolysis by sunlight.Environmental Degradation Pentobarbital has been positively identified (not quantified) in a ground-water sample collected from a well 300 m from a landfill which received wastes between 1968 and 1969 and re-sampling 21 years later (in 1991) revealed the presence of pentobarbital at a concentration of 1 mg l-1 which shows persistency of pentobarbital in the environment.

InChI:InChI=1/C11H18N2O3.Na/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);/q;+1

Upstream product

• 76-74-4 pentobarbital 

Downstream Products

• 76-75-5 thiopentone 

Relevant academic research and scientific papers

Preparation method of sodium 5-ethyl-5-(1-methylbutyl)barbiturate

The invention belongs to the field of pharmaceutical preparation and particularly relates to a preparation method of sodium 5-ethyl-5-(1-methylbutyl)barbiturate used before calming, hypnosis and anesthetization and as an anticonvulsant drug. The preparation method utilizes a 5-ethyl-5-(1-methylbutyl)malonylurea compound as a raw material. The preparation method comprises that A, 5-ethyl-5-(1-methylbutyl)malonylurea in an acetone solution and a methanol solution of sodium methylate undergo a reaction to produce a wet product of sodium 5-ethyl-5-(1-methylbutyl)barbiturate, and B, the product is subjected to vacuum drying to form a sodium 5-ethyl-5-(1-methylbutyl)barbiturate finished product. The preparation method has the advantages of stable processes, simple operation, short production period, good product quality, high purity, high yield, low production cost, low energy consumption, recovery and recycling of a mother liquid, few three wastes and industrial production feasibility.

Growth, shrinking, and breaking of pluronic micelles in the presence of drugs and/or β-cyclodextrin, a study by small-angle neutron scattering and fluorescence spectroscopy

The associative structures between F127 Pluronic micelles and four drugs, namely, lidocaine (LD), pentobarbital sodium salt (PB), sodium naproxen (NP), and sodium salicylate (SAL), were studied by small-angle neutron scattering (SANS). Different outcomes for the micellar aggregates are observed, which are dependent on the chemical nature of the drug and the presence of charge or otherwise: the micelles grow with LD, are hardly modified with PB, and decrease in size with both NP and SAL. The partition coefficient, determined by fluorescence spectroscopy, is directly correlated to the amount of charge, following NP ≈ SAL a slightly deeper localization of LD and more superficial for PB. All drugs can form inclusion complexes with heptakis(2,6-di-O-methyl) β-cyclodextrin (hep2,6 β-CD). Hep2,6 β-CD, as shown in previous studies (Joseph, J.; Dreiss, C. A.; Cosgrove, T. Langmuir, 2008, 24, 10005-10010; Dreiss, C. A.; Nwabunwanne, E.; Liu, R.; Brooks, N. J. Soft Matter, 2009, 5, 1888-1896), is also able to form a complex with F127, resulting in micellar breakup. In the ternary mixtures, a fine balance of forces is involved, which results in drastic micellar changes, as observed from the SANS patterns. Depending on the ratio of drug, polymer, and hep2,6 β-CD and the nature of the interactions (which is directly linked to the drug chemical structure), the presence of drug either hinders micellar breakup by β-CD (at high enough concentration of LD or PB) or leads to micellar growth (NP). These effects are mainly attributed to a preferential drug/β-CD interaction (except for PB), which, at least in the conditions studied here, explains the higher β-CD concentration needed for micellar breakup to occur.