ContaminantDB: Secobarbital

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (11)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:51 UTC

Update Date

2016-11-09 01:08:42 UTC

Accession Number

CHEM002190

Identification

Common Name

Secobarbital

Class

Small Molecule

Description

Secobarbital is only found in individuals that have used or taken this drug. It is a barbiturate derivative drug. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone. Secobarbital binds at a distinct binding site associated with a Cl^- ionopore at the GABA_A receptor, increasing the duration of time for which the Cl^- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Adjuvant
Adjuvant, Anesthesia
Amide
Amine
Barbiturate
Drug
GABA Modulator
Hypnotic and Sedative
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Secobarbital	ChEBI
5-(1-Methylbutyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Allyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Allyl-5-(1-methylbutyl)barbituric acid	ChEBI
5-Allyl-5-(1-methylbutyl)pyrimidine-2,4,6(1H,3H,5H)-trione	ChEBI
Quinalbarbitone	ChEBI
Secobarbitalum	ChEBI
Secobarbitone	ChEBI
Seconal	ChEBI
5-Allyl-5-(1-methylbutyl)barbitate	Generator
5-Allyl-5-(1-methylbutyl)barbitic acid	Generator
(+/-)-secobarbital	HMDB
Secobarbitale	HMDB
Sodium quinalbarbitone	HMDB
Sodium secobarbital	HMDB
Ranbaxy brand OF secobarbital sodium	HMDB
Secobarbital sodium	HMDB
Vangard brand OF secobarbital sodium	HMDB
Seconal sodium	HMDB
Sodium, secobarbital	HMDB
Meballymal	HMDB
Sebar	HMDB
Flynn brand OF secobarbital sodium	HMDB

Chemical Formula

C₁₂H₁₈N₂O₃

Average Molecular Mass

238.283 g/mol

Monoisotopic Mass

238.132 g/mol

CAS Registry Number

76-73-3

IUPAC Name

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

Traditional Name

secobarbital

SMILES

CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O

InChI Identifier

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Barbituric acid derivatives

Alternative Parents

Substituents

Barbiturate
N-acyl urea
Ureide
1,3-diazinane
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

barbiturates (CHEBI:9073 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

GABA modulator

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	100°C
Boiling Point	Not Available
Solubility	550 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	1.21 g/L	ALOGPS
logP	2.2	ALOGPS
logP	2.03	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.65 m³·mol⁻¹	ChemAxon
Polarizability	24.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9400000000-7060c19b726fabf79a65	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-0090000000-cd7b7b08df2b25a36a42	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9400000000-7060c19b726fabf79a65	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-0090000000-cd7b7b08df2b25a36a42	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fv-9640000000-bd64b937d195fac13712	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0190000000-db13804e78045568d611	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-d86de671e312eea0a25a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000f-9560000000-9d9b88d1074bc4050252	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-3ca3c567b6b2968e849d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-66fa917cc18fa12a1e35	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-0190000000-db13804e78045568d611	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1190000000-a32998e9d470646171bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1910000000-a7eedca671cea79ccabe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-008c-9100000000-27475f9b934cbdc3e650	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-8960000000-6fad2b5588666b99e2fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9710000000-a3d04768b9d678771dd4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-aa08a543bafa7b7a22bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-b039560fc84cd32f1088	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-91935f76c8fa79268cfc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-a49a216554329721fa1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0970000000-0de765aed5fb2211edc8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-1960000000-56c18517e4df3bf96800	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ldi-4900000000-03e38b2d7b88e080321d	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-6900000000-eb3ae85faebb012ef83b	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (1); Parenteral (1); Rectal (1).

Mechanism of Toxicity

Secobarbital binds at a distinct binding site associated with a Cl^- ionopore at the GABA_A receptor, increasing the duration of time for which the Cl^- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

Metabolism

Route of Elimination: Barbiturates are metabolized primarily by the hepatic microsomal enzyme system, and the metabolic products are excreted in the urine and, less commonly, in the feces.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the Short-term treatment of intractable insomnia for patients habituated to barbiturates

Minimum Risk Level

Not Available

Health Effects

Secobarbital causes slurred speech, disorientation and "drunken" behavior. It is physically and psychologically addictive.

Symptoms

Symptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00418

HMDB ID

HMDB0014562

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Link

General References

Not Available

Secobarbital (CHEM002190)

Structure for CHEM002190: Secobarbital