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Merck
CN

S1503

Supelco

Secobarbital

analytical standard

Synonym(s):

5-(1-Methylbutyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione, 5-Allyl-5-(1-methylbutyl)barbituric acid, Quinalbarbitone, Seconal

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About This Item

Empirical Formula (Hill Notation):
C12H18N2O3
CAS Number:
76-73-3
Molecular Weight:
238.28
EC Number:
200-982-2
MDL number:
MFCD00056088
UNSPSC Code:
41116107
PubChem Substance ID:
329824480
NACRES:
NA.24

Key Documents

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grade

analytical standard

drug control

USDEA Schedule II; Home Office Schedule 2; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IIC (Portugal); Pszichotróp anyag / Psychotropic Substance (Hungary), 78/2022. (XII. 28.) BM rendelet

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

SMILES string

O=C1C(CC=C)(C(C)CCC)C(NC(N1)=O)=O

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)

InChI key

KQPKPCNLIDLUMF-UHFFFAOYSA-N

Gene Information

human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562), GABRD(2563), GABRE(2564), GABRG1(2565), GABRG2(2566), GABRG3(2567), GABRP(2568), GABRQ(55879)

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General description

Secobarbital is a barbiturate sedative-hypnotic and anticonvulsant, mainly employed for preoperative sedation. It is commonly used for the short term treatment of insomnia, acute tetanus convulsions and acute psychotic agitation. Its mode of action involves functioning through the central nervous system (CNS) as a depressant with quick action.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Secobarbital may be used as an internal standard for the determination of barbiturates in biological samples using high-performance liquid chromatography technique. It may be used as an analytical reference standard for the quantification of the analyte in biological samples using gas chromatography technique.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品
This item has

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Certificates of Analysis (COA)

Lot/Batch Number
105H0534V
105H0534

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Desk Reference of Clinical Pharmacology, (2) (1983)
Application of thermoresponsive HPLC to forensic toxicology: determination of barbiturates in human urine
Kanno S, et al.
Forensic Toxicology, 27(2), 103-106 (2009)
Monitoring saliva concentrations of methaqualone, codeine, secobarbital, diphenhydramine and diazepam after single oral doses
Sharp.E.M, et al.
Journal of Analytical Toxicology, 7(1), 11-14 (1983)
Secobarbital poisoning in an Amur tiger (Panthera tigris altaica).
S Hewitt et al.
The Veterinary record, 167(5), 178-180 (2010-08-03)
Christopher M Anderson et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 22(21), 9203-9209 (2002-11-06)
Barbiturates are widely used as anesthetics, anticonvulsants, and neuroprotective agents. However, barbiturates may also inhibit mitochondrial respiration, and mitochondrial inhibitors are known to potentiate NMDA receptor-mediated neurotoxicity. Here we used rat cortical cultures to examine the effect of barbiturates on
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