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Talbutal

HCID 8275
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Basic information

CAS
115-44-6
Standard SMILES
C=CCC1(C(C)CC)C(=O)NC(=O)NC1=O
InChIKey
BJVVMKUXKQHWJK-UHFFFAOYSA-N
Molecular formula
C11H16N2O3
Average molar mass
224.26 g/mol
Monoisotopic mass
224.11609238

Overview

Talbutal is a member of barbiturates.

Names & identifiers

Preferred name
Talbutal
IUPAC
5-butan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
English name
TALBUTAL CIII (250 MG)
Molecular formula
C11H16N2O3
Molecular weight
224.26

Names & synonyms

TALBUTALLotusateProfundol115-44-65-Allyl-5-sec-butylbarbituric acidTalbutaleTalbutalumsec-Butyl allyl barbituric acidWIN 5095DTXSID8023630Barbituric acid, 5-allyl-5-sec-butyl-4YIR8202AX
Show more names
LatusateTALBUTAL CIII (250 MG)sec-butylallylbarbituricacid5-isobutyl-5-allylbarbituricacid5-allyl-5-sec-butyl-barbituricaci5-allyl-5-sec-butylbarbituricacid
2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylpropyl)-5-(2-propenyl)-DTXCID4036305-(butan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trioneRefChem:56087allyl-sec-butyl-barbituric acidN05CA07204-090-4Talbutal [INN]

Database identifiers

CAS
115-44-6
PubChem CID
8275
DTXSID
DTXSID8023630
ChEMBL
CHEMBL1200802
ChEBI
CHEBI:134923
UNII
4YIR8202AX
EC Number
204-090-4
Nikkaji
J47.150J

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
75.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
16
Formal charge
0
Complexity
329

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Barbiturates

pHSATURATED AQ SOLN IS ACID TO LITMUS
LogP1.47
OdorMAY HAVE SLIGHT ODOR OF CARAMEL
TasteSLIGHTLY BITTER TASTE
Color/Form · 2 items

CRYSTALS FROM WATER OR DIL ALCOHOL

WHITE, CRYSTALLINE POWDER

SolubilityPRACTICALLY INSOL IN WATER & PETROLEUM ETHER SOL IN ALCOHOL, CHLOROFORM, ETHER, ACETONE, GLACIAL ACETIC ACID, FIXED ALKALI HYDROXIDE SOLN
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point108-110 °C
Dissociation Constants · 2 items

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

FDA Requirements · 5 items

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

5-Allyl-5-sec-butylbarbituric acid is a chemical derivative of barbituric acid, named in section 502(d) of the Federal Food, Drug, and Cosmetic Act, and is hereby designated as habit forming.

Warning and caution statements for 5-allyl-5-sec-butylbarbituric acid specifically required by law. PREPARATIONS CONTAINING HABIT-FORMING DERIVATIVES OF SUBSTANCES NAMED IN SECTION 502(d) OF THE FEDERAL FOOD, DRUG, AND COSMETIC ACT ... The statement "Warning-May be habit forming" is required to appear on the labels of all drugs containing derivatives designated in 21 CFR 329.1 ... as habit forming.

Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III includes any substance which contains any quantity of a derivative of barbituric acid or any salt thereof. DEA Code #2100; Drug class: Depressant. /Derivatives of barbituric acid or any salt thereof/

For more FDA Requirements (Complete) data for TALBUTAL (7 total), please visit the HSDB record page.

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety & protection

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Pharmacodynamics · 1 item

Talbutal is a short to intermediate-acting barbiturate that is a nonselective central nervous system (CNS) depressant. As with other barbiturates, talbutal is capable of producing all levels of CNS mood alteration from excitation to mild sedation, hypnosis, and deep coma. Barbiturates may also induce anesthesia at sufficiently high therapeutic doses.

Mechanism of Action · 6 items

Talbutal binds to GABA<sub>A</sub> receptors at a distinct binding site associated with a Cl<sup>-</sup> ionopore of the receptor. Upon binding, talbutal increases the duration of time for which the Cl<sup>-</sup> ionopore is open, leading to prolonged inhibitory effect of GABA at the postsynaptic thalamic neuron.

BARBITURATES REVERSIBLY DEPRESS ACTIVITY OF ALL EXCITABLE TISSUES. NOT ALL TISSUES ARE AFFECTED @ SAME DOSE OR CONCN; CNS IS EXQUISITELY SENSITIVE, SO THAT WHEN BARBITURATES ARE GIVEN IN SEDATIVE OR HYPNOTIC DOSES, VERY LITTLE EFFECT ON SKELETAL, CARDIAC, OR SMOOTH MUSCLE OCCURS. /BARBITURATES/

... RETICULAR ACTIVATING SYSTEM IS EXQUISITELY SENSITIVE TO DEPRESSANT EFFECTS OF BARBITURATES ... WHATEVER ... EFFECTS OF BARBITURATES ELSEWHERE IN CNS, IT IS EFFECT ON RETICULAR SYSTEM THAT SEEMS TO BE RESPONSIBLE FOR INABILITY TO MAINTAIN WAKEFULNESS UNDER INFLUENCE OF BARBITURATE. /BARBITURATES/

BARBITURATES ARE RESP DEPRESSANTS, AFFECTING BOTH DRIVE TO RESP & MECHANISM RESPONSIBLE FOR RHYTHMIC CHARACTER OF RESP MOVEMENT. /BARBITURATES/

The mechanism(s) of action of the barbiturates is not completely known. Although the drugs act throughout the CNS, a site of particular sensitivity is the polysynaptic midbrain reticular formation which is concerned with the arousal mechanism. Barbiturates induce an imbalance in central inhibitory and facilitatory mechanisms influencing the cerebral cortex and the reticualar formation. The significance of the effect of barbiturates on neurotransmitters is unclear. It appears that the drugs decrease the excitability of both presynaptic and postsynaptic membranes. It has not been determined which of the various actions of barbiturates at cellular and synaptic levels are responsible for their sedative and hypnotic effects. /Barbiturates/

For more Mechanism of Action (Complete) data for TALBUTAL (9 total), please visit the HSDB record page.

Related reactions

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Compound notes

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7.79 (at 25 °C)

PKA: ABOUT 9.4

Other Experimental PropertiesMAY OCCUR IN POLYMORPHIC FORM THAT MELTS @ ABOUT 111 °C

Physicochemical properties

Melting point
108 · 108-110°
Boiling point
365.66 °C · 365.66°C (rough estimate)
Density
1.1672 · 1.1672 (rough estimate)
refractive index
1.5 · 1.5000 (estimate)
solubility
Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
form
Solid
color
White to Off-White
Water Solubility
2.16 g/L · 2.16g/L(temperature not stated)
EWG's Food Scores
1 · 1
FDA UNII
4 YIR8202AX · 4YIR8202AX
EPA Substance Registry System
2 · 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylpropyl)-5-(2-propen-1-yl)- (115-44-6)
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301
Precautionary statements
264 · P264-P270-P301+P310-P321-P330-P405-P501
RIDADR
3249 · 3249
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Hazardous Substances Data
115 · 115-44-6(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in rats: 57.5 mg/kg (Schafer)
Storage Conditions
Store below 40 °C (104 °F), preferably between 15 and 30 °C. ... Store in a tight container.

Toxicology

Body BurdenBarbiturates are distributed into the milk of nursing women. /Barbiturates/
Interactions · 5 items

... BARBITURATES MAY CAUSE DECR HYPOPROTHROMBINEMIC EFFECT OF ORAL ANTICOAGULANTS. ... BARBITURATES INTERACT WITH ADRENAL CORTICOSTEROIDS TO CAUSE REDUCED SERUM LEVELS & DECR SYSTEMIC EFFECTS OF STEROIDS; PROBABLE MECHANISM IS INDUCTION OF MICROSOMAL ACTIVITY. /BARBITURATES/

DECR SERUM LEVELS OF DOXYCYCLINE (VIBRAMYCIN) ... REPORTED WHEN BARBITURATE ... GIVEN CONCURRENTLY; PROBABLE MECHANISM IS INDUCTION OF MICROSOMAL ENZYME ACTIVITY. DECR SERUM LEVELS OF GRISEOFULVIN ... NOTED ... CHLORPROMAZINE MAY BE MORE RAPIDLY METABOLIZED WHEN BARBITURATES ... GIVEN CONCURRENTLY. /BARBITURATES/

MONOAMINE OXIDASE INHIBITORS POTENTIATE ACTION OF BARBITURATES ... /BARBITURATES/

LETHAL BLOOD ... /LEVEL/ ... MAY BE ... 1 MG/100 ML FOR INTERMEDIATE- & SHORT-ACTING BARBITURATES; IF OTHER DEPRESSANT DRUGS OR ALC ARE ALSO PRESENT, LETHAL CONCN MAY BE EVEN LOWER. /BARBITURATES, SHORT & INTERMEDIATE ACTING/

For more Interactions (Complete) data for TALBUTAL (16 total), please visit the HSDB record page.

Milk ConcentrationsBarbiturates are distributed into the milk of nursing women. /Barbiturates/
Human Toxicity Excerpts · 5 items

SEVERE OLIGURIA OR ANURIA MAY OCCUR IN ACUTE ... POISONING, LARGELY AS RESULT OF MARKED HYPOTENSION. /BARBITURATES/

BARBITURATES COMBINE WITH CYTOCHROME P-450 & ... COMPETITIVELY INTERFERE WITH BIOTRANSFORMATIONS OF ... /ITS/ SUBSTRATES. /BARBITURATES/

SHORT-ACTING BARBITURATES ARE MORE POTENT &, OF COURSE, MORE TOXIC THAN LONG-ACTING COMPD. /BARBITURATES, SHORT-ACTING/

May be habit forming.

For more Human Toxicity Excerpts (Complete) data for TALBUTAL (13 total), please visit the HSDB record page.

Non-Human Toxicity Excerpts · 1 item

IN ACUTE BARBITURATE POISONING RESPIRATION BECOMES SHALLOW & LOW &, WHEN INTOXICATION IS FULLY DEVELOPED, THERE IS EXTREME LETHARGY & COMA, WITH DISAPPEARANCE OF REFLEXES; PUPILS BECOME DILATED. DEATH OCCURS FROM RESP FAILURE, DUE TO DEPRESSION OF RESPIRATORY CENTER. /BARBITURATES/

Antidote and Emergency Treatment · 4 items

TREATMENT: Stabilization: Respiratory arrest is the major cause of early death. Assess the patency of the airway and the adequacy of ventilation first. Appropriate corrective measures include supplemental oxygen, head tilt-chin lift, intubation, and assisted ventilation. Establish an iv line with Ringer's lactate and give a fluid challenge up to 2 l for patients who are hypotensive. Cardiac dysrhythmias are rare but were reported. ... Be sure to give glucose, naloxone, and thiamine to all patients with depressed mental status. /Barbiturates/

Gut Decontamination: Because of decr gastrointestinal mobility and delayed gastric emptying, gut decontamination is indicated 6-8 hr postingestion in obtunded patients. Barbiturates are well absorbed by charcoal; 10 times the ingested dose (or 1 g/kg body weight) should be given together with a cathartic (sorbitol, magnesium citrate) to all patients. /Barbiturates/

Elimination Enhancement: Most overdose patients respond to supportive care and require no special measures. ... Alkaline diuresis is ineffective for short and intermediate acting barbiturates. ... Hemoperfusion: This measure is more effective than dialysis for short and intermediate acting barbiturates. ...

Antidotes: No effective antidotes are available. Respiratory and central nervous stimulants incr complications and should be avoided. /Barbiturates/

Regulatory information

FDA Requirements · 5 items

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

5-Allyl-5-sec-butylbarbituric acid is a chemical derivative of barbituric acid, named in section 502(d) of the Federal Food, Drug, and Cosmetic Act, and is hereby designated as habit forming.

Warning and caution statements for 5-allyl-5-sec-butylbarbituric acid specifically required by law. PREPARATIONS CONTAINING HABIT-FORMING DERIVATIVES OF SUBSTANCES NAMED IN SECTION 502(d) OF THE FEDERAL FOOD, DRUG, AND COSMETIC ACT ... The statement "Warning-May be habit forming" is required to appear on the labels of all drugs containing derivatives designated in 21 CFR 329.1 ... as habit forming.

Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III includes any substance which contains any quantity of a derivative of barbituric acid or any salt thereof. DEA Code #2100; Drug class: Depressant. /Derivatives of barbituric acid or any salt thereof/

For more FDA Requirements (Complete) data for TALBUTAL (7 total), please visit the HSDB record page.

Safety data

ridadr
3249
Toxicity
LD50 orally in rats: 57.5 mg/kg (Schafer)
Signal word
Danger
Symbol(GHS)
GHS06
hazard_class
6.1(b)
packing_group
III
Hazard statements
H301
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501
Hazardous Substances Data
115-44-6(Hazardous Substances Data)
Biological Half-LifeHalf-life 15 hr
Metabolism/Metabolites · 3 items

MOST BARBITURATES ARE TRANSFORMED IN BODY TO INACTIVE METABOLITES. PRINCIPAL SITE OF BIOTRANSFORMATION IS LIVER. OXYBARBITURATES ARE TRANSFORMED ONLY BY LIVER; THIOBARBITURATES MAY BE TRANSFORMED TO SMALL EXTENT IN OTHER TISSUES, ESP KIDNEY & BRAIN ... /BARBITURATES/

Hepatic biotransformation, primarily by the hepatic microsomal enzyme system. /Barbiturates/

With the exception of the less lipid-soluble aprobarbital and phenobarbital, nearly complete metabolism and/or conjugation of barbiturates in the liver precedes their renal excretion. The oxidation of radicals at C5 is the most important biotransformation responsible for termination of biological activity. Oxidation results in the formation of alcohols, kentones, phenols, or carboxylic acids, which may appear in the urine as such or as glucuronic acid conjugates. In some instances (e.g., phenobarbital), N-glucosylation is an important metabolic pathway. Other biotransformations include N-hydroxylation, desulfuration of thiobarbiturates to oxybarbiturates, opening of the barbituric acid ring, and N-dealkylation of N-alkylbarbiturates to active metabolites (e.g., mephobarbital to phenobarbital).

Absorption, Distribution and Excretion · 5 items

THERE EXISTS NO IMPENETRABLE BARRIER TO DIFFUSION OF BARBITURATES IN BODY ... SMALL AMT ... MAY APPEAR IN MILK AFTER INGESTION OF LARGE DOSES. ... READILY CROSS PLACENTAL BARRIER, &, WITHIN FEW MIN AFTER INJECTION OF SHORT-... ACTING BARBITURATE, CONCN IN FETAL BLOOD APPROACHES THAT IN MATERNAL VENOUS BLOOD. /BARBITURATES/

THREE MOST IMPORTANT FACTORS AFFECTING DISTRIBUTION & FATE OF BARBITURATES ARE LIPID SOLUBILITY ... PROTEIN BINDING, & EXTENT OF IONIZATION. ... THE MORE HIGHLY LIPID-SOL COMPD ARE SHORT-ACTING AGENTS... THEY TEND TO BE MORE RAPIDLY DEGRADED METABOLICALLY & ARE ALMOST COMPLETELY REABSORBED BY RENAL TUBULE. /BARBITURATES/

For sedative hypnotic use, the barbiturates are usually administered orally. Such doses are rapidly and probably completely absorbed; sodium salts are absorbed more rapidly than the corresponding free acids, especially from liquid formulations. The onset of action varies from 10 to 60 min, depending upon the agent and the formulation, and is delayed by the presence of food in stomach. /Barbiturates/

Barbiturates are distributed widely and readily cross the placenta. Binding to plasma proteins is a function of lipid solubility and is greatest for thiopental, which is bound to the extent of 65% or more. The highly lipid soluble barbiturates, led by those used to induce anesthesia, undergo redistribution after intravenous injection. Uptake into less vascular tissue, especially muscle and fat, leads to a decline in the concentration of barbiturate in the plasma and brain.

Elimination/% excreted unchanged: renal/trace

Uses & manufacturing

UsesMEDICATION
Methods of ManufacturingBY GENERAL METHOD DESCRIBED ... /FOR BARBITAL/ USING ALLYL BROMIDE & SEC-BUTYL BROMIDE AS ALKYLATING AGENTS.
Formulations/Preparations · 2 items

LOTUSATE (WINTHROP). DOSAGE FORMS--TABLETS NF (TABLET IN CAPSULE FORM): 30, 50, & 120 MG.

Lotusate Caplets, oral caplets with talbutal 120 mg, lactose, magnesium stearate, starch, talc.

Applications

UsesA stuctural isomer of Butalbital (B690100). A short to intermediate-acting barbiturate that act as nonselective depressants of the central nervous system (CNS). Sedative, hypnotic. Controlled Substance.

Additional notes

DefinitionChEBI: Talbutal is a member of barbiturates.