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(±)-Hexobarbital

(±)-Hexobarbital structure

CAS No:
56-29-1
Formula:
C12H16N2O3
Chemical Name:
(±)-Hexobarbital
Synonyms:
2,4,6(1H,3H,5H)-Pyrimidinetrione,5-(1-cyclohexen-1-yl)-1,5-dimethyl-;Barbituric acid,5-(1-cyclohexen-1-yl)-1,5-dimethyl-;5-(1-Cyclohexen-1-yl)-1,5-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione;Citopan;5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbituric acid;Cyclonal;Cyclopan;1,5-Dimethyl-5-(1-cyclohexenyl)barbituric acid;Dorico;Enhexymal;Evipal;Hexanastab Oral;Hexobarbital;Hexobarbitone;Methexenyl;N-Methyl-5-cyclohexenyl-5-methylbarbituric acid;Noctivane;Sombulex;Somnalert;Hexenal (barbiturate);Narcosan;5-(1-Cyclohexenyl-1)-1-methyl-5-methylbarbituric acid;Methylhexabital;Evipan;Barbidorm;Citodon;(±)-Hexobarbitone;(±)-Hexobarbital;(RS)-Hexobarbital;Sombucaps;Methylhexabarbital;NSC 71929;(±)-5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbituric acid;630-97-7;7200-11-5
Categories:
Analytical Chemistry > Standard

Description

White crystals.

Solid

Hexobarbital is a member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups. It derives from a barbituric acid.|A barbiturate that is effective as a hypnotic and sedative.

(±)-Hexobarbital Basic Attributes

Molecular Weight：

236.27

Exact Mass：

236.27

EC Number：

200-264-9

NSC Number：

71929

DSSTox ID：

DTXSID9023122

ATC Code：

N - Nervous system

Characteristics

PSA：

66.5

XLogP3：

1.98

Appearance：

Solid

Density：

1.225 g/cm3

Melting Point：

146.5 °C

Boiling Point：

368.8ºC at 760 mmHg

Flash Point：

11 °C

Refractive Index：

1.5460 (estimate)

Water Solubility：

434.7mg/L(25 ºC)

Storage Conditions：

2-8°C

PKA：

8.2None

Dissociation Constants：

8.2

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

3249

wgk germany：

hazard class code：

22-39/23/24/25-23/24/25-11

safety instructions：

36/37/39-45-36/37-16-7

RTECS Number：

CQ2625000

Marks：

Xn,T,F

Precautionary statement(s)：

P210-P260-P280-P301 + P310-P311

Hazard Statements：

H225-H301 + H311 + H331-H370

RIDADR：

UN 3249

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity Summary：

Symptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.

Protein Binding：

25%

Drug Information

Drug Indication：

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.

Pharmacology：

Hexobarbital is a barbiturate derivative having hypnotic and sedative effects. It was subsequently used in the 1940s and 1950s as an anesthetic for surgery. Furthermore, the agent also demonstrates a fairly quick onset of action that also possesses a short duration of action. However it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine, usually thiopental would be the barbiturate of choice for this application these days.

MeSH：

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)|Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)

Metabolism/Metabolites：

Hepatic.

Mechanism of Action：

Hexobarbital 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.

MeSH Entry Terms：

Evipan

(±)-Hexobarbital Use and Manufacturing

Medicine (sedative).

Computed Properties

Molecular Weight:236.27
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:236.11609238
Monoisotopic Mass:236.11609238
Topological Polar Surface Area:66.5
Heavy Atom Count:17
Complexity:428
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes