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Aprobarbital

HCID 6464
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
77-02-1
Standard SMILES
C=CCC1(C(C)C)C(=O)NC(=O)NC1=O
InChIKey
UORJNBVJVRLXMQ-UHFFFAOYSA-N
Molecular formula
C10H14N2O3
Average molar mass
210.23 g/mol
Monoisotopic mass
210.10044231

Overview

Aprobarbital is a member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by an isopropyl and a prop-1-en-3-yl group at position 5.

Names & identifiers

Preferred name
Aprobarbital
IUPAC
5-propan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
English name
APROBARBITAL METHANOL SOLUTION
Molecular formula
C10H14N2O3
Molecular weight
210.23

Names & synonyms

APROBARBITALAllypropymalAlurateAllylpropymalAprobarbitoneAllonalAllionalAprozalNumal77-02-1Alurate elixir verdum5-Allyl-5-isopropylbarbituric acid
Show more names
IsonalNSC120769Aprobarbita
AllylisopropylmalonylureaIsopropylallylbarbituric acid5-Isopropyl-5-allylbarbituric acidAllylisopropylbarbituric acidAprobarbitalumBarbituric acid, 5-allyl-5-isopropyl-Q0YKG9L6RF5-(1-Methylethyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione

Database identifiers

CAS
77-02-1
PubChem CID
6464
DTXSID
DTXSID8022616
ChEMBL
CHEMBL7863
ChEBI
CHEBI:2791
UNII
Q0YKG9L6RF
EC Number
200-997-4
Nikkaji
J38.379A

Properties

Computed structural properties

XLogP
1.1
Topological polar surface area
75.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
15
Formal charge
0
Complexity
314

Experimental & physicochemical properties

Drugs · 3 items

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Barbiturates

Pharmaceuticals -> Listed in ZINC15

pHA SATURATED AQUEOUS SOLN IS ACID TO LITMUS
SpringerMaterials PropertiesDensity
LogP · 2 items

1.15

1.22

TasteSLIGHTLY BITTER
Color/Form · 2 items

CRYSTALS

Fine, white, crystalline powder

Solubility · 4 items

POWDER; HYGROSCOPIC; SLIGHTLY BITTER TASTE; VERY SOL IN WATER; SLIGHTLY SOL IN ALC; PRACTICALLY INSOL IN ETHER; AQ SOLN ARE ALKALINE TO LITMUS /APROBARBITAL SODIUM SALT/

ALMOST INSOL IN WATER, PETROLEUM ETHER, ALIPHATIC HYDROCARBONS; SOL IN ALC, CHLOROFORM, ETHER, ACETONE, BENZENE, GLACIAL ACETIC ACID, FIXED ALKALI HYDROXIDE SOLN.

Lipid solubility is low.

5.17e+00 g/L

DecompositionWhen heated to decomp it emits toxic fumes of oxides of nitrogen. /Aprobarbital sodium/

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)

Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Other Safety InformationIMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylethyl)-5-(2-propenyl)-: Human health tier I assessment
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-isopropylbarbituric 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-isopropylbarbituric 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 APROBARBITAL (6 total), please visit the HSDB record page.

Hazard Classes and Categories

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Mechanism of Action · 6 items

Aprobarbital (like all barbiturates) works by binding to the GABAA receptor at either the alpha or the beta sub unit. These are binding sites that are distinct from GABA itself and also distinct from the benzodiazepine binding site. Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor. This GABAA receptor binding decreases input resistance, depresses burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increases both the amplitude and decay time of inhibitory postsynaptic currents. In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. Glutamate is the principal excitatory neurotransmitter in the mammalian CNS. Aprobarbital also appears to bind neuronal nicotinic acetylcholine receptors.

... REVERSIBLY DEPRESS ACTIVITY OF ALL EXCITABLE TISSUES. ... CNS IS ... SENSITIVE, SO ... IN SEDATIVE OR HYPNOTIC DOSES, VERY LITTLE EFFECT ON SKELETAL, CARDIAC, OR SMOOTH MUSCLE OCCURS. ... PROBABLE THAT EXCITABILITY IN EACH TISSUE IS DEPRESSED BY AN ACTION ON OR IN A MEMBRANE & THAT ... MECHANISMS ... ARE ... SIMILAR. /BARBITURATES/

AS DOSE ... INCR, HYPOXIC & CHEM DRIVES TO RESP ARE DIMINISHED ... HOWEVER, HYPOXIC DRIVE PERSISTS @ LEVELS OF INTOXICATION CAUSING ... INSENSITIVITY OF RESP CENTERS TO CO2. ... AS INTOXICATION /INCR/ ... THERE IS SHIFT IN CONTROL OF RESP FROM CO2-SENSITIVE AREAS OF MEDULLA TO MORE PRIMITIVE ... CAROTID & AORTIC ... /BARBITURATES/

WHATEVER ... THE EFFECTS OF BARBITURATES ELSEWHERE IN CNS, IT IS EFFECT ON RETICULAR SYSTEM ... RESPONSIBLE FOR INABILITY TO MAINTAIN WAKEFULNESS UNDER INFLUENCE OF A BARBITURATE. /BARBITURATES/

BARBITURATES DECR TURNOVER OF 5-HYDROXYTRYPTAMINE & CATECHOLAMINES IN BRAIN OF EXPTL ANIMALS, BUT WHETHER THIS IS CAUSE OR EFFECT OF ANESTHESIA IS CONJECTURAL. /BARBITURATES/

For more Mechanism of Action (Complete) data for APROBARBITAL (10 total), please visit the HSDB record page.

Biological Half-Life · 2 items

APROBARBITAL DOSE 0.75 G ORAL REACHED CONCN 2.3 MG% IN 3-9 HR; T/2 WAS 24-36 HR. /FROM TABLE/

Plasma half-life is about 14 fto 40 hours.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Melting Point · 2 items

140-141.5 °C

141 °C

Refractive IndexINDEX OF REFRACTION ALPHA: 1.520; BETA: 1.581; GAMMA: 1.600
Physical DescriptionSolid
Stability/Shelf LifeSTABLE IN AIR

Physicochemical properties

Melting point
140 · 140-141.5°
Boiling point
349.75 °C · 349.75°C (rough estimate)
Density
1.2056 · 1.2056 (rough estimate)
refractive index
1.5 · 1.5000 (estimate)
storage temp.
2 · 2-8°C
solubility
DMSO (Slightly), Methanol (Slightly)
pka
7.81 · 7.81±0.10(Predicted)
form
Solid
color
White to Off-White
Water Solubility
4.121 g/L · 4.121g/L(25 ºC)
Major Application
forensics and toxicology
InChI
1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)
InChIKey
UORJNBVJVRLXMQ-UHFFFAOYSA-N
SMILES
O=C1C(C(C)C)(CC=C)C(NC(N1)=O)=O
FDA UNII
0 YKG9L6RF · Q0YKG9L6RF
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301
Precautionary statements
264 · P264-P270-P301+P310-P321-P330-P405-P501
target organs
Eyes,Central nervous system
Hazard Codes
F,T
Risk Statements
11 · 11-23/25-36/38
Safety Statements
16 · 16-24-45
WGK Germany
2 · WGK 2
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Hazardous Substances Data
77 · 77-02-1(Hazardous Substances Data)
Toxicity
50 i.p · LD50 i.p. in mice: 200 mg/kg (Frey)
DEA Controlled Substances
2100 CSA · CSCN: 2100CSA SCH: Schedule IIINARC: No
Acute Tox. 3 (100%)

Safety & protection

Storage ConditionsOral solution should be stored in tight, light-resistant containers at a temperature less than 40 °C, preferably between 15 to 30 °C; freezing should be avoided. ... Expiration date /is/ 4 years following the date of manufacture.

Toxicology

Interactions · 5 items

IN CAT CEREBRAL CORTEX, BARBITURATES IN ANESTHETIC DOSES SELECTIVELY ABOLISH EXCITATION BUT NOT INHIBITION ELICITED BY NOREPINEPHRINE APPLIED DIRECTLY TO VARIOUS SYNAPSES... /BARBITURATES/

AT SKELETAL NEUROMUSCULAR JUNCTIONS BLOCKING EFFECTS OF BOTH D-TUBOCURARINE & DECAMETHONIUM ARE ENHANCED BY BARBITURATES. /BARBITURATES/

BOTH CARDIAC GLYCOSIDES & BETA-ADRENERGIC AGONISTS ANTAGONIZE MYOCARDIAL DEPRESSANT ACTION /OF BARBITURATES/. /BARBITURATES/

INTENSITY OF CNS DEPRESSION CAN BE INCR BY ACIDIC DRUGS SUCH AS ASPIRIN ... WHICH DISPLACE BARBITURATES FROM PLASMA PROTEINS. /BARBITURATES/

For more Interactions (Complete) data for APROBARBITAL (14 total), please visit the HSDB record page.

Human Toxicity Excerpts · 5 items

... BARBITURATES REDUCE AMT OF TIME SPENT IN REM PHASE SLEEP, &, IN THIS ... BARBITURATE-INDUCED SLEEP DIFFERS FROM PHYSIOLOGICAL SLEEP. ... CLAIMED ... THAT DEPRIVATION OF THIS PHASE ... MAY HAVE DELETERIOUS EFFECTS. SUBJECTS DEPRIVED OF REM ... EXHIBIT REBOUND INCR IN ... TIME SPENT IN REM SLEEP FOLLOWING ... DEPRIVATION. /BARBITURATE/

PROLONGED USE OF BARBITURATES INCR RESTLESSNESS DURING LATE STAGES OF SLEEP, CAUSES ANXIETY, & INCR PLASMA CONCN OF GROWTH HORMONE BUT DECR THOSE OF ADRENOCORTICOIDS. ... IN SMALL DOSES, BARBITURATES MAY INCR REACTION TO PAINFUL STIMULI. /BARBITURATES/

OXYBARBITURATES TEND TO DECR TONUS OF GI MUSCULATURE & AMPLITUDE OF RHYTHMIC CONTRACTIONS. /OXYBARBITURATES/

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

For more Human Toxicity Excerpts (Complete) data for APROBARBITAL (17 total), please visit the HSDB record page.

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-isopropylbarbituric 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-isopropylbarbituric 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 APROBARBITAL (6 total), please visit the HSDB record page.

Safety data

wgk
WGK 2
Toxicity
LD50 i.p. in mice: 200 mg/kg (Frey)
risk_code
11-23/25-36/38
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
F,T
safety_code
16-24-45
Storage Class
3 - Flammable liquids
target organs
Eyes,Central nervous system
Hazard statements
H301
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501
DEA Controlled Substances
CSCN: 2100CSA SCH: Schedule IIINARC: No
Hazardous Substances Data
77-02-1(Hazardous Substances Data)
Metabolism/Metabolites · 4 items

PARTLY METABOLIZED IN LIVER BY OXIDN OF C-5 SUBSTITUENT(S) (ALLYL &/OR ISOPROPYL GROUPS) ... ALLYL GROUP ... MAY ALSO /BE REMOVED/. RESULTING /IN/ INACTIVE METABOLITES /HUMAN, ORAL/.

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

Partially metabolized in the liver by oxidation of the C5 substituent(s) (allyl and/or isopropyl groups). Removal of the allyl group at C5 may also occur. The resulting inactive metbolites, which have not been identified are excreted in the urine.

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, ketones, phenols, or carboxylic acids, which may appear in the urine as such or as glucuronic acid conjugates. In some instances (eg, 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 (eg, mephobarbital to phenobarbital).

Absorption, Distribution and Excretion · 5 items

RATE OF DECLINE OF BLOOD CONCN AFTER A LARGE DOSE FOR ... ALURATE ... IS 25-40% /PER 24 HR/ ... RATE OF DECLINE IS A FUNCTION OF ACCUMULATION IN LIVER, METAB OF DRUG & URINARY EXCRETION.

AS MUCH AS 50% OF HYPNOTIC DOSE OF ... APROBARBITAL MAY BE EXCRETED UNCHANGED BY KIDNEY. ... APROBARBITAL ... ELIMINATED SLOWLY, OVER A PERIOD OF SEVERAL DAYS.

A FRACTION OF BARBITURATE IN BLOOD IS REVERSIBLY BOUND TO PLASMA PROTEIN, CHIEFLY ALBUMIN. ... THE CEREBROSPINAL FLUID IS VIRTUALLY PROTEIN FREE. ACCORDINGLY, THE MAXIMAL CONCN OF BARBITURATES ATTAINED IN CEREBROSPINAL FLUID IS LESS THAN THE PLASMA CONCN, BEING IN MOST CASES SLIGHTLY LESS THAN THE CONCN IN AN ULTRAFILTRATE OF PLASMA. THE CONCN IN OCULAR FLUID IS SIMILAR TO THAT OF CEREBROSPINAL FLUID. IN TISSUES, THE BARBITURATE CONCN IS GENERALLY AS HIGH AS OR SLIGHTLY HIGHER THAN IN PLASMA. /BARBITURATES/

... SODIUM SALTS ARE MORE RAPIDLY ABSORBED THAN FREE ACIDS ... FOOD IN STOMACH DECR RATE OF ABSORPTION BUT NOT AMT ABSORBED. THERE EXISTS NO IMPENETRABLE BARRIER TO ... BARBITURATES IN BODY ... IF SOJOURN OF DRUG IN PLASMA IS SUFFICIENTLY LONG, IT WILL BE DISTRIBUTED TO ALL TISSUES & FLUIDS. /BARBITURATES/

For more Absorption, Distribution and Excretion (Complete) data for APROBARBITAL (10 total), please visit the HSDB record page.

Cellular LocationsMembrane

Uses & manufacturing

UsesMEDICATION
Formulations/Preparations · 2 items

Alurate Elixir, oral solution with aprobarbital 40 mg/5 ml and alcohol 20%.

Oral solution: 40 mg/5 ml, Alierate on Elixis (C-III with 20% alc)

Applications

UsesControlled substance (depressant). Sedative, hypnotic.

Upstream & downstream products

Upstream raw materials

Sodium hydroxideAllyl bromide5-ISOPROPYLBARBITURIC ACID

Additional notes

DefinitionChEBI: A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by an isopropyl and a prop-1-en-3-yl group at position 5.