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Pentobarbital

CAS No.
76-74-4
Chemical Name:
Pentobarbital
Synonyms
C07422;Mebumal;Neodorm;Dorsital;Nembutal;Rivadorm;Ethaminal;Mebubarbital;neodorm(new);Neodorm (new)
CBNumber:
CB5402863
Molecular Formula:
C11H18N2O3
Molecular Weight:
226.27
MDL Number:
MFCD00057561
MOL File:
76-74-4.mol
Last updated:2023-06-08 09:02:48

Pentobarbital Properties

Melting point 129.5°C
Boiling point 367.89°C (rough estimate)
Density 1.1376 (rough estimate)
refractive index 1.4620 (estimate)
Flash point 9℃
storage temp. 2-8°C
solubility Very slightly soluble in water, freely soluble in ethanol. It forms water-soluble compounds with alkali hydroxides and carbonates and with ammonia.
form A neat solid
pka pK1:8.11(0) (25°C)
Water Solubility 679 mg/L
CAS DataBase Reference 76-74-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII I4744080IR
ATC code N05CA01
NIST Chemistry Reference Pentobarbital(76-74-4)
EPA Substance Registry System Pentobarbital (76-74-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H301-H336-H361d
Precautionary statements  P201-P202-P261-P264-P270-P301+P310
Hazard Codes  T,F
Risk Statements  25-63-39/23/24/25-36/38-23/24/25-11
Safety Statements  7-16-36/37-45-36/37/39-22
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  CQ5775000
HazardClass  6.1(b)
PackingGroup  III
HS Code  2933530000
Toxicity A barbiturate that causes CNS depression, apparently due to a facilitation of GABA-ergic inhibition. It appears that the site of action of pentobarbital may be the macromolecular complex made up of a GABA receptor, chloride channel, benzodiazepine-binding site, and picrotoxin-binding site. Barbiturates have been shown to compete for dihydropicrotoxinin-binding sites. In clinical use, barbiturates such as pentobarbital have been largely replaced as sedative-hypnotics by the much safer benzodiazepines. The sedative-hypnotic properties of barbiturates may lead to abuse, as tolerance and dependence are known to occur. In animals, pentobarbital is routinely used for its anesthetic and anticonvulsant properties, as well as for euthanasia. Pentobarbital, like other barbiturates, can induce the metabolism of other compounds by altering cytochrome P450 activity. The oral LD50 in rats is 118 mg/kg.
NFPA 704
0
3 0

Pentobarbital price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P-010 Pentobarbital solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 76-74-4 1mL $27.7 2024-03-01 Buy
Sigma-Aldrich 1507002 Pentobarbital United States Pharmacopeia (USP) Reference Standard 76-74-4 200mg $581 2024-03-01 Buy
Cayman Chemical 20966 Pentobarbital (CRM) 76-74-4 1mg $22 2023-06-20 Buy
Cayman Chemical 20965 Pentobarbital 76-74-4 5mg $59 2023-06-20 Buy
Cayman Chemical 20965 Pentobarbital 76-74-4 1mg $20 2023-06-20 Buy
Product number Packaging Price Buy
P-010 1mL $27.7 Buy
1507002 200mg $581 Buy
20966 1mg $22 Buy
20965 5mg $59 Buy
20965 1mg $20 Buy

Pentobarbital Chemical Properties,Uses,Production

Description

Pentobarbital (CRM) (Item No. 20966) is a certified reference material categorized as a barbiturate. Pentobarbital is regulated as a Schedule II compound in the United States. Pentobarbital (CRM) (Item No. 20966) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.

Chemical Properties

A white or almost white, crystalline powder or colourless crystals

Originator

Nembutal,Abbott,US

Uses

Sedative-hypnotic.

Definition

ChEBI: A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.

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)[Name previously used: Pentobarbitone.];Aethaminalum;Barbityral;Barbopent;Burtylonel;Cafergot p.b.;Calpental;Di-barbs;Dipental;Distonocalm;Ergobel plus;Hypnol;Hypnotal;Hyptonal;Insom rapido;Isoamytal;Isom rapido;Iturate;Narcoren;Nembudeine;Nicaphlogyl;Novarectal;Nova-rectal;Novopentobarb;Novo-pentobarb;Or-trin;Palpent;Pembul;Penbon;Pentalgin;Pentanca;Pentodormol;Pentogen;Pentolos;Petab;Petonel;Praecicalm;Prodormol;Somnophyt;Somnotol;S-spac;Stopp-15;Wans;Wigraine-pb;Yastyl.

Therapeutic Function

Hypnotic, Sedative

World Health Organization (WHO)

Pentobarbital is a short-acting barbiturate which is controlled under Schedule III of the 1971 Convention on Psychotropic Substances. See WHO comment for barbiturates. (Reference: (UNCPS3) United Nations Convention on Psychotropic Substances (III), , , 1971)

Purification Methods

A solution of the sodium salt in 10% HCl is prepared, and the acid is extracted with ether. Evaporation of the extract gives a solid which is then purified by repeated crystallisation from CHCl3. It sublimes at 95-105o/10-12mm. [Bucket & Sandorfy J Phys Chem 88 3274 1984.] The (+)-and (-)-enantiomers crystallise from 50% aqueous EtOH with m 120-121o and have [] 25 +4.73o to –4.93o (EtOH) [Kleiderer & Shonle J Am Chem Soc 56 1772 1934]. [Beilstein 24

76-72-2
57-13-6
76-74-4
Synthesis of Pentobarbital from Diethyl ethyl(1-methylbutyl)malonate and Urea
5-Ethyl-5-(1-methylbutyl)malonylurea 5-Ethyl-5-(sec-pentyl)barbituric acid 5-ethyl-5-(sec-pentyl)barbituricacid 6(1h,3h,5h)-pyrimidinetrione,5-ethyl-5-(1-methylbutyl)-4 Barbituric acid, 5-ethyl-5-(1-methylbutyl)- barbituricacid,5-ethyl-5-(2-pentyl) component of Emesert Dorsital Ethaminal Ethyl-propylmethylcarbinylbarbituric acid ethyl-propylmethylcarbinylbarbituricacid Mebubarbital Mebumal Nembutal Neodorm Neodorm (new) neodorm(new) Pentabarbital Pentabarbitone pentobarbitalum Pentobarbiturate Pentobarbituric acid pentobarbituricacid Rivadorm PENTOBARBITAL pentobarbitone 5-ethyl-5-(1-methylbutyl)barbituric acid 5-ETHYL-5-[1-METHYLBUTYL]-2,4,6-TRIOXOHEXAHYDROPYRIMIDINE 5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione pentobarbital free acid--dea*schedule ii item pentobarbital methanol solution PENTOBARBITAL FREE ACID--DEA*SCHEDULE II PENTOBARBITAL,USP 5-Ethyl-5-(1-methylbutyl)-2,4,6-trioxohexahydropyrimidine, Nembutal Pentobarbital solution (-)-5-Ethyl-5-[(S)-1-methylbutyl]-2,4,6(1H,3H,5H)-pyrimidinetrione (-)-5-Ethyl-5-[(S)-1-methylbutyl]barbituric acid (+)-5-Ethyl-5-[(R)-1-methylbutyl]-2,4,6(1H,3H,5H)-pyrimidinetrione (+)-5-Ethyl-5-[(R)-1-methylbutyl]barbituric acid C07422 Pentobarbital CII (200 mg) 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylbutyl)- 5-Ethyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione 5-Ethyl-5-(1-methylbutyl)barbituric acidcid 5-ethyl-5-(1-methylbutyl)-barbituricaci WEXRUCMBJFQVBZ-UHFFFAOYSA-N Pentobarbitone Solution, 1000ppm Pentobarbitone Solution, 100ppm Pentobarbital (CRM) 5-ethyl-5-[(1RS)- 1-methylbutyl]pyrimidine-2,4,6(1H,3H,5H)-trione Pentobarbital USP/EP/BP Thiopental Sodium and Sodium Carbonate EP Impurity B Thiopental Sodium and Sodium Carbonate Impurity B 76-74-4 C11H18N2O3