T3DB: Butabarbital

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (6)XML

Targets (6)

Record Information

Version

2.0

Creation Date

2009-07-21 20:26:21 UTC

Update Date

2014-12-24 20:25:50 UTC

Accession Number

T3D2721

Identification

Common Name

Butabarbital

Class

Small Molecule

Description

Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital.

Compound Type

Amide
Amine
Anti-Anxiety Agent
Barbiturate
Drug
Hypnotic and Sedative
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
5-Ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
5-Ethyl-5-(1-methylpropyl)barbituric acid
5-Sec-butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
5-Sec-butyl-5-ethylbarbituric acid
5-Sec-butyl-5-ethylpyrimidine-2,4,6(1H,3H,5H)-trione
Butabarbitone
Butalan
Butisol
Butrate
Sarisol No. 2
Secbubarbital
Secbutabarbital
Secbutobarbital
Secbutobarbitone
Sodium Butabarbital

Chemical Formula

C₁₀H₁₆N₂O₃

Average Molecular Mass

212.246 g/mol

Monoisotopic Mass

212.116 g/mol

CAS Registry Number

125-40-6

IUPAC Name

5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione

Traditional Name

butabarbital

SMILES

CCC(C)C1(CC)C(O)=NC(=O)N=C1O

InChI Identifier

InChI=1/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)

InChI Key

InChIKey=ZRIHAIZYIMGOAB-UHFFFAOYNA-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:3228 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	166.5°C
Boiling Point	Not Available
Solubility	1360 mg/L
LogP	1.65

Predicted Properties

Property	Value	Source
Water Solubility	1.39 g/L	ALOGPS
logP	1.7	ALOGPS
logP	1.45	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	8.48	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	3	ChemAxon
Refractivity	53.4 m³·mol⁻¹	ChemAxon
Polarizability	21.41 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7i-8900000000-fc5f17ec8979e31b77ac	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1290000000-73748d3c96bdcbc7692d	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-3900000000-c62b6d06318be5ee7a26	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-d815b39070a4a2b620ee	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0296-8950000000-e8d3b0ea461e5ad69068	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9500000000-43d75b9170cae3f239fa	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9400000000-ec7399384bd48aaa6ee4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-121a04bb64c32af4a00f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3900000000-58caeb294d4571a30cf4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9300000000-527f2d60d78505d84953	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1290000000-994157d74b9e27e50e2d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-85bbea89298999fca7c3	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-6900000000-6e0cbc3d26c5541ad8eb	2014-09-20	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Butabarbital 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. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.

Metabolism

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

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures;

Minimum Risk Level

Not Available

Health Effects

They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.

Symptoms

Signs of overdose include confusion (severe), decrease in or loss of reflexes, drowsiness (severe), fever, irritability (continuing), low body temperature, poor judgment, shortness of breath or slow or troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness (severe).

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

3228

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Butabarbital

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Butabarbital

References

Synthesis Reference

Not Available

MSDS

T3D2721.pdf

General References

Drugs.com [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Neuronal acetylcholine receptor subunit alpha-4

General Function:: Ligand-gated ion channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
Gene Name:: CHRNA4
Uniprot ID:: P43681
Molecular Weight:: 69956.47 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [11264449 ]
Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [16248797 ]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [10487207 ]

Target Details

2. Neuronal acetylcholine receptor subunit alpha-7

General Function:: Toxic substance binding
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
Gene Name:: CHRNA7
Uniprot ID:: P36544
Molecular Weight:: 56448.925 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [11264449 ]
Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [16248797 ]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [10487207 ]

3. GABA-A receptor (anion channel) (Protein Group)

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Included Proteins:: P14867 , P47869 , P34903 , P48169 , P31644 , Q16445 , P18505 , P47870 , P28472 , O14764 , P78334 , Q8N1C3 , P18507 , Q99928 , O00591 , Q9UN88

References

Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [10209232 ]
Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [11264449 ]

Target Details

4. Gamma-aminobutyric acid receptor subunit alpha-1

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular Weight:: 51801.395 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]

Target Details

5. Glutamate receptor 2

General Function:: Ionotropic glutamate receptor activity
Specific Function:: Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. In the presence of CACNG4 or CACNG7 or CACNG8, shows resensitization which is characterized by a delayed accumulation of current flux upon continued application of glutamate.
Gene Name:: GRIA2
Uniprot ID:: P42262
Molecular Weight:: 98820.32 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [11264449 ]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [10487207 ]

Target Details

6. Glutamate receptor ionotropic, kainate 2

General Function:: Kainate selective glutamate receptor activity
Specific Function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus. Modulates cell surface expression of NETO2 (By similarity).
Gene Name:: GRIK2
Uniprot ID:: Q13002
Molecular Weight:: 102582.475 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [11264449 ]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [10487207 ]

Butabarbital (T3D2721)

Structure for T3D2721: Butabarbital

Targets

References

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