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Home > Encyclopedia > 2,4,6(1H,3H,5H)-Pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-

2,4,6(1H,3H,5H)-Pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-

pharmaceutical raw materials
2,4,6(1H,3H,5H)-Pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)- structure

2,4,6(1H,3H,5H)-Pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)- 

structure
  • CAS No:

    151-83-7

  • Formula:

    C14H18N2O3

  • Chemical Name:

    2,4,6(1H,3H,5H)-Pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-

  • Synonyms:

    2,4,6(1H,3H,5H)-Pyrimidinetrione,1-methyl-5-(1-methyl-2-pentyn-1-yl)-5-(2-propen-1-yl)-;Barbituric acid,5-allyl-1-methyl-5-(1-methyl-2-pentynyl)-;2,4,6(1H,3H,5H)-Pyrimidinetrione,1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-;1-Methyl-5-(1-methyl-2-pentyn-1-yl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione;5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric acid;Compound 22451;Compound 25398;Methodrexitone;Methohexital;Methohexitone;Brietal;Brevital;Enallynymall;115621-33-5;7187-72-6;18652-93-2

  • Categories:

    Analytical Chemistry  >  Standard

Description

ChEBI: A barbiturate, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by allyl and 1-methylpent-2-ynyl groups.


Solid


Methohexital is a barbiturate, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by allyl and 1-methylpent-2-ynyl groups. It has a role as an intravenous anaesthetic and a drug allergen. It is a member of barbiturates and an acetylenic compound. It is a conjugate acid of a methohexital(1-).|Methohexital is a DEA Schedule IV controlled substance. Substances in the DEA Schedule IV have a low potential for abuse relative to substances in Schedule III.|An intravenous anesthetic with a short duration of action that may be used for induction of anesthesia.|Methohexital is a Barbiturate.|Methohexital is a rapid, short-acting barbituric acid derivative, with anesthetic activity. Methohexital binds to the chloride ionophore site of the gamma-aminobutyric acid (GABA)-A/chloride ionophore receptor complex, thereby enhancing the inhibitory actions of GABA-A in the brain. This leads to synaptic inhibition, decreased neuronal excitability, and induction of anesthesia. In addition, this agent decreases glutamate (Glu) responses.

2,4,6(1H,3H,5H)-Pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)- Basic Attributes

262.3

262.30

205-798-6

E5B8ND5IPE

2264

DTXSID1023287

C66116

N - Nervous system

2933599550

Characteristics

66.5

1.8

Solid

1.113

96 °C @ Solvent: Ethanol

1.504

5.24e-02 g/L

2-8°C

Safety Information

III

6.1(b)

3249

11-23/24/25-39/23/24/25

16-36/37-45

F,T

Missing Phrase - N15.00950417

H301

Toxicity

The onset of toxicity following an overdose of intravenously administered methohexital will be within seconds of the infusion. If methohexital is administered rectally or is ingested, the onset of toxicity may be delayed. The manifestations of an ultrashort-acting barbiturate in overdose include central nervous system depression, respiratory depression, hypotension, loss of peripheral vascular resistance, and muscular hyperactivity ranging from twitching to convulsive-like movements. Other findings may include convulsions and allergic reactions. Following massive exposure to any barbiturate, pulmonary edema, circulatory collapse with loss of peripheral vascular tone, and cardiac arrest may occur.

73%

Drug Information

Methohexital is indicated for use as an intravenous anaesthetic. It has also been commonly used to induce deep sedation.|FDA Label

Methohexital, a barbiturate, is used for the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.

Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)

The absolute bioavailability following rectal administration of methohexital is 17%.|Excretion occurs via the kidneys through glomerular filtration.

Metabolism occurs in the liver through demethylation and oxidation. Side-chain oxidation is the most important biotransformation involved in termination of biologic activity.

5.6 ± 2.7 minutes

Methohexital binds at a distinct binding site associated with a Cl- ionopore at the GABAA 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.

Brevimytal Natrium

Methohexital|Brevital|2264|Schedule IV - Substances in the DEA Schedule IV have a low potential for abuse relative to substances in Schedule III.|No

2,4,6(1H,3H,5H)-Pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)- Use and Manufacturing

Methohexital is a short-acting barbiturate used as a sedative. Methohexital is used an anesthetic for oral surgery and dentistry and is also used to induce anesthesia prior to electroconvulsive therapy (ECT). Methohexital is a Controlled Substance.

Computed Properties

Molecular Weight:262.30
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:262.13174244
Monoisotopic Mass:262.13174244
Topological Polar Surface Area:66.5
Heavy Atom Count:19
Complexity:497
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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