Secbutabarbital

Butrate · Nilox · Butatab · Butatal · Butisol · Secumal · Butabarb · Buticaps

Identifikatoren & physikalische Daten

CAS No.	125-40-6
Summenformel	C10H16N2O3
Durchschnittliche Molmasse	212,25 g/mol
Monoisotopische Masse	212,11609237 g/mol
SMILES	CCC(C)C1(CC)C(=O)NC(=O)NC1=O
InChIKey	ZRIHAIZYIMGOAB-UHFFFAOYSA-N
PubChem CID	2479
ChEMBL	CHEMBL449
ChEBI	CHEBI:3228
EC No.	204-738-6
DTXSID	DTXSID2022709
Lokaler Name	Secbutabarbital

Chemische & physikalische Eigenschaften

XLogP	1,6
Polarare Oberfläche (TPSA)	75,3
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	3
Schwere Atome	15
Formalladung	0
Komplexität	292
Arzneimittel	DEA NFLIS-Drug Category -> Depressants and Tranquilizers
SpringerMaterials Properties	Nuclear quadrupole resonance spectroscopy
LogP (Verteilungskoeffizient)	log Kow = 1.651.5
Geruch	Odorless
Geschmack	Bitter
Color/Form	Fine, white, microcrystalline powder
Löslichkeit	WHITE POWDERPRACTICALLY INSOL IN BENZENE & ABS ETHER /SODIUM SALT/1.39e+00 g/LDMSO (Slightly), Methanol (Slightly)848.3mg/L(25 ºC)
Human Drugs	Breast FeedingLactationMilk, HumanBarbituratesHypnotics and SedativesGABA ModulatorsPharmaceuticals
Decomposition	When heated to decomp it emits toxic fumes of oxides of /nitric oxide/.
Schmelzpunkt	165-168 °C166.5 °C166.5°C
Brechungsindex	INDEX OF REFRACTION: 1.465 (ALPHA)1.529 (BETA)1.532 (GAMMA) /SODIUM SALT/1.4550 (estimate)
Physical Description	Solid
Siedepunkt	352.08°C (rough estimate)
Dichte	1.1718 (rough estimate)
Flammpunkt	9℃
Lagerbedingungen	-20°C
Aggregatzustand	Solid
pKa (Säurekonstante)	7.93±0.10(Predicted)
Farbe	White
CAS Datenbank	125-40-6
EPA chemische Informationen	2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)- (125-40-6)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH301 (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 43 reports by companies from 1 notifications to the ECHA C&L Inventory.
Weitere Sicherheitsinformationen	IMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-: Human health tier I assessment
FDA-Anforderungen	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including butabarbital sodium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Butabarbital sodium/Butabarbital sodium 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. /Butabarbital sodium/Schedule III shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Each drug or substance has been assigned the DEA Controlled Substances Code Number set forth opposite it. ... Depressants: Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation which contains any quantity of the following substances having a depressant effect on the central nervous system: Any substance which contains any quantity of a derivative of barbituric acid or any salt thereof. DEA Code Number: 2100. /Derivatives of barbituric acid or any salt thereof/
Special Reports	DHHS/NIDAResearch Monographs Series 73: Urine Testing for Drugs of Abuse (1986)[Available from, as of March 29, 2010: http://www.nida.nih.gov/pdf/monographs/download73.html]
Hazard Classes and Categories	Acute Tox. 3 (100%)
Skin, Eye, and Respiratory Irritations	May cause irritation. Remove to fresh air. Flush with copious quantities of water.
Hazardous Reactivities and Incompatibilities	Solutions of butabarbital sodium should not be added to acidic solutions because precipitation of butabarbital may occur.
Brandbekämpfungsverfahren	Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials.As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
Lagerbedingungen	Store in tight container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.Store at controlled room temperature 20-25 °C (68-77 °F). Dispense in a tight container.
Reinigungsverfahren	Wipe up spillage or collect spillage using a high- efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.
Entsorgungsverfahren	SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
Preventive Measures	This material is assumed to be combustible. As with all dry powders, it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling./Use/ safety goggles and protect exposed skin.
Personal Protective Equipment (PPE)	Engineering controls such as exhaust ventilation are recommended.Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.
Wechselwirkungen	Concurrent administration of disulfiram with barbiturates may result in inhibition of metabolism of the barbiturates and an increased incidence of barbiturate toxic effects. /Barbiturates/Concurrent use with barbiturates may result in increased metabolism, leading to decreased serum concentrations and reduced elimination half-lives of carbamazepine or succinimide anticonvulsants because of induction of hepatic microsomal enzyme activity. Monitoring of serum concentrations as a guide to dosage is recommended, especially when carbamazepine or a succinimide anticonvulsant is added to or withdrawn from an existing regimen. /Barbiturates/Concurrent use with barbiturates, especially phenobarbital, may induce microsomal metabolism to increase formation of alkylating metabolites of cyclophosphamide, thereby reducing the half-life and increasing the leukopenic activity of cyclophosphamide. /Barbiturates/Concurrent use with barbiturates, especially phenobarbital, may reduce serum disopyramide to ineffective concentrationstherefore, monitoring of its serum concentrations is necessary during concurrent therapy. /Barbiturates/For more Interactions (Complete) data for Butabarbital (38 total), please visit the HSDB record page.
Gesundheitliche Auswirkungen	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.
Milk Concentrations	The /barbiturates/ are distributed into milk in concentrations much lower than those in plasma. /Barbiturates General Statement/
Toxizitätsübersicht	Butabarbital binds at a distinct binding site associated with a Cl<sup>-</sup> ionopore at the GABA<sub>A</sub> receptor, increasing the duration of time for which the Cl<sup>-</sup> 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.
Signs and 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).
Human Toxicity Excerpts	/SIGNS AND SYMPTOMS/ Symptoms of acute intoxication with barbiturates include unsteady gait, slurred speech, and sustained nystagmus. Mental signs of chronic intoxication include confusion, poor judgment, irritability, insomnia, and somatic complaints. Barbiturate intoxication may be confused with alcoholism, bromide intoxication, and with various neurological disorders./SIGNS AND SYMPTOMS/ Acute overdosage with barbiturates is manifested by CNS and respiratory depression which may progress to Cheyne-Stokes respiration, areflexia, constriction of the pupils to a slight degree (though in severe poisoning they may show paralytic dilation), oliguria, tachycardia, hypotension, lowered body temperature, and coma. Typical shock syndrome (apnea, circulatory collapse, respiratory arrest, and death) may occur./SIGNS AND SYMPTOMS/ In extreme overdose, all electrical activity in the brain may cease, in which case a "flat" EEG normally equated with clinical death cannot be accepted. This effect is fully reversible unless hypoxic damage occurs. Consideration should be given to the possibility of barbiturate intoxication even in situations that appear to involve trauma./SIGNS AND SYMPTOMS/ Symptomatology ... Drowsiness is usually first symptom. Transient period of confusion, excitement, delirium, and perhaps hallucinations is not uncommon. Ataxia, vertigo, slurred speech, headache, paresthesias, and subjective visual disturbances. Stupor progressing through deepening states of coma, with inhibition or absence of superficial and deep reflexes. Responses to painful stimuli gradually cease. Babinski toe sign may become positive. Respirations may be rapid and shallow or slow and labored, but min vol (pulmonary ventilation) is always reduced. Mild but progressive cardiovascular collapse, evidence by cyanosis, hypotension, weak rapid pulse, and cold and clammy skin. Circulatory insufficiency may or may not be result of hypoxia from respiratory depression. Transient electrocardiographic changes may be seen ... Pupils ... usually slightly constricted ... They may dilate during terminal asphyxia. Urine formation is slowed or suppressed completely. Body temp ... usually reduced. If fever develops, it usually signals bronchopneumonia but paradoxical hyperpyrexia is recognized as rare complication. Respirations become irregular, sometimes Cheyne-Stokes in character, and eventually cease. Although death is usually due to respiratory arrest, circulatory shock may be proximal cause. Occasionally severe grades of pulmonary edema ... are encountered ... Hypostatic or aspiration pneumonia late in course of illness may prove lethal. Renal shutdown due to circulatory collapse can complicate illness but is rarely irreversible. Among survivors, residual damage is rare, but occasional patient who has suffered prolonged and severe hypoxia during acute phase may exhibit permanent neurological damage. Irregular erythematous cutaneous lesions and bullae containing clear fluid are seen in many patients. Allergic reactions from acquired hypersensitivity are ... asthma, urticaria, angioneurotic edema, dermatitis, fever, delirium, liver necrosis. /Barbiturates/For more Human Toxicity Excerpts (Complete) data for Butabarbital (6 total), please visit the HSDB record page.
Carcinogen Classification	No indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts	/OTHER TOXICITY INFORMATION/ No long-term studies in animals have been performed with butabarbital sodium to determine carcinogenic and mutagenic potential, or effects on fertility.
Populations at Special Risk	Hypersensitivity reactions to barbiturates include urticaria, angioedema, morbilliform or scarlatiniform rash, fever, serum sickness, erythema multiforme, or Stevens-Johnson syndrome. Hypersensitivity reactions are most likely to occur in patients with asthma, urticaria, or angioedema. Rarely, photosensitivity reactions have been reported. Phenobarbital, metharbital, and mephobarbital appear to cause rashes more frequently than do other barbiturates. Exfoliative dermatitis, which may be accompanied by hepatitis and jaundice, has occurred rarely and has resulted in a few fatalities. Rarely, cutaneous reactions have preceded the development of barbiturate-induced systemic lupus erythematosus. Adverse cutaneous reactions may proceed to an irreversible stage even though the medication has been discontinued, because barbiturates are slowly metabolized and excreted. /Barbiturates General Statement/Barbiturates may elevate blood ammonia. Animal studies indicate that thiopental impairs the ability of the liver to metabolize ammonia. For this reason, it has been suggested that barbiturate administration be avoided in patients with ammonia intoxication. /Barbiturates/
Antidote and Emergency Treatment	/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B//SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/Emergency and supportive measures. Protect the airway and assist ventilation if necessary. Treat coma, hypothermia, and hypotension if they occur. /Barbiturates/For more Antidote and Emergency Treatment (Complete) data for Butabarbital (6 total), please visit the HSDB record page.
Effects During Pregnancy and Lactation	◉ Summary of Use during Lactation
Wassergefährdungsklasse (WGK)	1
UN-Transportnummer	3249
Zollcode	2933530000
R-Sätze (R)	11-23/24/25-39/23/24/25-25
Gefahrensymbole	F,T
Sicherheitshinweise (S)	16-36/37-45
Gefahrenklasse	6.1(b)
Verpackungsgruppe	III
Gefahrstoffdaten	125-40-6(Hazardous Substances Data)

Anwendungen & Verwendung

Beschreibung

Butabarbital (CRM) (Item No. 20088) is a certified reference material categorized as a barbiturate. It has a high abuse potential and increases risk of overdose morbidity and mortality in recreational drug users. Butabarbital is regulated as a Schedule III compound in the United States. Butabarbital (CRM) (Item No. 20088) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.

Verwenden

Butabarbital is also used as a soporific drug in various forms of insomnia and as a sedative. The most frequently used synonym is butizone.