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Merck
CN

S1503

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
NACRES:
NA.24
PubChem Substance ID:
329824480
UNSPSC Code:
41116107
EC Number:
200-982-2
MDL number:
MFCD00056088

Key Documents

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InChI key

KQPKPCNLIDLUMF-UHFFFAOYSA-N

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)

SMILES string

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

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, kontrollierte Droge in Deutschland

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)

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

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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.

Legal Information

German
Dieses Produkt fällt unter das Betäubungsmittelgesetz (BtMG). Für eine Bestellung dieses Produktes ist eine Erlaubnis nach § 3 BtMG zwingend erforderlich, es sei denn, es greift eine Ausnahme von der Erlaubnispflicht nach § 4 oder § 26 BtMG.

English
This product is subject to the German Narcotics Act. A permit under Section 3 of the German Narcotics Act is mandatory for ordering this product unless an exemption from the permit requirement under Section 4 or Section 26 of the German Narcotics Act applies.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

监管及禁止进口产品
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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)
T C Whiting et al.
Journal of analytical toxicology, 25(3), 179-189 (2001-05-01)
In order to achieve accurate quantitation of drugs and metabolites (analytes) in complex matrices, 2H- (and less commonly 13C-) labeled analogues of the analytes are now routinely adapted as the internal standards (IS) using linear calibration models to fit data
Robert T Gerhardt et al.
The American journal of emergency medicine, 29(1), 86-90 (2010-09-10)
The objective of the study was to determine whether the addition of postdischarge oral secobarbital to standard emergency department (ED) migraine headache therapy improves pain relief and headache resolution compared with placebo. The setting is an urban ED with 70
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