5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

• ChemBase ID: 130315
• Molecular Formular: C12H18N2O3
• Molecular Mass: 238.28292
• Monoisotopic Mass: 238.13174245
• SMILES: O=C1NC(=O)NC(=O)C1(C(C)CCC)CC=C
• Canonical SMILES: CCCC(C1(CC=C)C(=O)NC(=O)NC1=O)C
• InChI: InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
• InChIKey: KQPKPCNLIDLUMF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: secobarbital
• Brand Name: Seconal
• Synonyms: Secobarbital solution; Secobarbital; Secobarbital; 5-(1-Methylbutyl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione; (RS)-Secobarbital; (+/-)-Quinalbarbitone; 5-Allyl-5-(1-methylbutyl)barbituric Acid; Evronal; Hypotrol; Immenox; Meballymal; Quinalbarbital; Quinalbarbitone; Secobarbitone; Seconal; Somatarax; 司可巴比妥 溶液; 5-烯丙基-5-(1-甲基丁基)巴比妥酸; 西康乐; 速可眠; 司可巴比妥

Database IDs

• CAS Number: 76-73-3
• EC Number: 200-982-2
• MDL Number: MFCD00056088
• PubChem SID: 24899579; 24899481; 162224594
• PubChem CID: 5193
• CHEBI ID: 9073
• ATC CODE: QN51AA02; N05CA06
• CHEMBL: 447
• Chemspider ID: 5005
• DrugBank ID: DB00418
• KEGG ID: D00430
• Unique Ingredient Identifier: 1P7H87IN75
• Wikipedia Title: Secobarbital
• Medline Plus: a682386

CALCULATED PROPERTIES

• Acid pKa: 8.478766
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.0333812
• LogD (pH = 7.4): 1.9994502
• Log P: 2.0338318
• Molar Refractivity: 62.648 cm^3
• Polarizability: 24.39162 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 11 °C; 51.8 °F

Safety Information

• RTECS: CP9450000
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230; 2811
• German water hazard class: 1; 3
• Hazard Class: 3; 6.1
• Packing Group: 2; 3
• Risk Statements: 11-23/24/25-39/23/24/25; 25-36/37/38
• Safety Statements: 16-36/37-45; 26-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H311-H331-H370; H301-H315-H319-H335
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311; P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1230 3/PG 2; UN 2811 6.1/PG 3
• Drug Control: Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Half Life: 15-40 hours
• Metabolism: Hepatic
• Protein Bound: 45-60%
• Legal Status: Schedule II, except when combined in a dosage unit with another active drug (in which case Schedule III) (US)
• Pregnancy Category: D (United States)

Product Information

• Concentration: 1.0 mg/mL in methanol; 1.0 mg/mL±5% in methanol
• Grade: analytical standard, for drug analysis

DETAILS

Toronto Research Chemicals - S235000

Barbiturates are being widely used as antiepileptics, hypnotics, and anesthetics.Controlled substance.

REFERENCES

• Inaba, T., et al.: Clin. Pharm. Ther., 20, 439 (1976)
• Sun, S., et al.: J. Pharm. Sci., 66, 477 (1976)
• Coudore, F., et al.: J .Anal. Toxicol., 17, 109 (1976)
• Ferslew, K., et al.: J. Forensic Sci., 40, 245 (1976)