Reclazepam

Last updated
Reclazepam
Reclazepam.svg
Clinical data
ATC code
  • none
Identifiers
  • 2-[7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1,4-benzodiazepin-1-yl]-1,3-oxazol-4-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C18H13Cl2N3O2
Molar mass 374.22 g·mol−1
3D model (JSmol)
  • Clc1ccccc1/C4=N/CCN(C\2=N\C(=O)CO/2)c3ccc(Cl)cc34
  • InChI=1S/C18H13Cl2N3O2/c19-11-5-6-15-13(9-11)17(12-3-1-2-4-14(12)20)21-7-8-23(15)18-22-16(24)10-25-18/h1-6,9H,7-8,10H2 Yes check.svgY
  • Key:MQGIGGJUPITZSE-UHFFFAOYSA-N Yes check.svgY
   (verify)

Reclazepam is a drug which is a benzodiazepine derivative. It has sedative and anxiolytic effects similar to those produced by other benzodiazepine derivatives, and has a short duration of action. [1]

Contents

Synthesis

Patent: Chloroacetyl isocyanate: Prec: Reclazepam synthesis.svg
Patent: Chloroacetyl isocyanate: Prec:

The reduction of the lactam in Delorazepam with lithium aluminium hydride gives CID:20333776 (1). Condensation with 2-chloroacetylisocyanate [4461-30-7] (2) proceeds to afford urea, CID:20333773 (3). Reaction of that with sodium iodide and base probably proceeds initially by halogen exchange of iodine for chlorine (Finkelstein reaction). Subsequent replacement of iodide by the enol anion of the urea oxygen results in formation of the oxazolone ring. There is thus obtained reclazepam (4).

See also

Related Research Articles

Demethylation is the chemical process resulting in the removal of a methyl group (CH3) from a molecule. A common way of demethylation is the replacement of a methyl group by a hydrogen atom, resulting in a net loss of one carbon and two hydrogen atoms.

<span class="mw-page-title-main">Amobarbital</span> Barbiturate

Amobarbital is a drug that is a barbiturate derivative. It has sedative-hypnotic properties. It is a white crystalline powder with no odor and a slightly bitter taste. It was first synthesized in Germany in 1923. It is considered a short to intermediate acting barbiturate.

<span class="mw-page-title-main">Oxibendazole</span> Chemical compound

Oxibendazole is a benzimidazole drug that is used to protect against roundworms, strongyles, threadworms, pinworms and lungworm infestations in horses and some domestic pets. It is usually white to yellowish in appearance, and may take the form of a powder, tablet or paste.

<span class="mw-page-title-main">Thiourea</span> Organosulfur compound (S=C(NH2)2)

Thiourea is an organosulfur compound with the formula SC(NH2)2 and the structure H2N−C(=S)−NH2. It is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom ; however, the properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. Thioureas are a broad class of compounds with the general structure R2N−C(=S)−NR2.

<span class="mw-page-title-main">Sulfamic acid</span> Chemical compound

Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, sulphamic acid and sulfamidic acid, is a molecular compound with the formula H3NSO3. This colourless, water-soluble compound finds many applications. Sulfamic acid melts at 205 °C before decomposing at higher temperatures to water, sulfur trioxide, sulfur dioxide and nitrogen.

<span class="mw-page-title-main">Potassium cyanate</span> Chemical compound

Potassium cyanate is an inorganic compound with the formula KOCN. It is a colourless solid. It is used to prepare many other compounds including useful herbicide. Worldwide production of the potassium and sodium salts was 20,000 tons in 2006.

<span class="mw-page-title-main">Thiophenol</span> Chemical compound

Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols. An exception is the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom.

<span class="mw-page-title-main">Methohexital</span> Anesthetic and barbiturate-type sedative

Methohexital or methohexitone is a drug which is a barbiturate derivative. It is classified as short-acting, and has a rapid onset of action. It is similar in its effects to sodium thiopental, a drug with which it competed in the market for anesthetics.

Ethotoin is an anticonvulsant drug used in the treatment of epilepsy. It is a hydantoin, similar to phenytoin. It is not available in the United States.

<span class="mw-page-title-main">Ethinamate</span> Pharmaceutical drug

Ethinamate is a short-acting carbamate-derivative sedative-hypnotic medication used to treat insomnia. Regular use leads to drug tolerance, and it is usually not effective for more than 7 days. Prolonged use can lead to dependence.

<span class="mw-page-title-main">Semicarbazide</span> Chemical compound

Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.

<span class="mw-page-title-main">Rosoxacin</span> Antibiotic

Rosoxacin is a quinolone antibiotic indicated for the treatment of urinary tract infections and certain sexually transmitted diseases. Rosoxacin is not available in the United States.

Trifluorotoluene is an organic compound with the formula of C6H5CF3. This colorless fluorocarbon is used as a specialty solvent in organic synthesis and an intermediate in the production of pesticides and pharmaceuticals.

<span class="mw-page-title-main">Zomebazam</span> Chemical compound

Zomebazam produced by Hoechst is a pyrazolodiazepinone derivative drug with anxiolytic properties. It is structurally related to razobazam and zometapine.

<span class="mw-page-title-main">Binedaline</span> Chemical compound

Binedaline (also called binodaline or binedaline hydrochloride;) is a drug that was investigated as an antidepressant in the 1980s but was never marketed. It acts as a selective norepinephrine reuptake inhibitor (Ki = 25 nM), with relatively insignificant influence on the serotonin (Ki = 847 nM) and dopamine (Ki >= 2 μM) transporters. It has negligible affinity for the α-adrenergic, mACh, H1, or 5-HT2 receptors.

<span class="mw-page-title-main">Diethyl carbonate</span> Chemical compound

Diethyl carbonate (sometimes abbreviated DEC) is an ester of carbonic acid and ethanol with the formula OC(OCH2CH3)2. At room temperature (25 °C) diethyl carbonate is a colorless liquid with a low flash point.

<span class="mw-page-title-main">Dimethylol ethylene urea</span> Chemical compound

Dimethylol ethyleneurea is an organic compound derived from formaldehyde and urea. It is a colourless solid that is used for treating cellulose-based heavy fabrics to inhibit wrinkle formation. Dimethylol ethylene urea (DMEU) bonds with the hydroxyl groups present in long cellulose chains and prevents the formation hydrogen bonding between the chains, the primary cause of wrinkling. This treatment produces permanently wrinkle-resistant fabrics and is different from the effects achieved from using fabric softeners. An additional names for DMEU includes 1,3-bis(hydroxymethyl)-tetrahydro-2-imidazolone.

<span class="mw-page-title-main">Pyrazolam</span> Benzodiazepine

Pyrazolam (SH-I-04) is a benzodiazepine derivative originally developed by a team led by Leo Sternbach at Hoffman-La Roche in the 1970s. It has since been "rediscovered" and sold as a designer drug since 2012.

<span class="mw-page-title-main">Prorenone</span> Chemical compound

Prorenone is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed. It is the lactonic form of prorenoic acid (prorenoate), and prorenoate potassium (SC-23992), the potassium salt of prorenoic acid, also exists. Prorenoate potassium is about 8 times more potent than spironolactone as an antimineralocorticoid in animals, and it may act as a prodrug to prorenone. In addition to the mineralocorticoid receptor, prorenone also binds to the glucocorticoid, androgen, and progesterone receptors. The antiandrogenic potency of prorenone in vivo in animals is close to that of spironolactone. Similarly to spironolactone, prorenone is also a potent inhibitor of aldosterone biosynthesis.

<span class="mw-page-title-main">Dimethylcarbamoyl chloride</span> Chemical compound

Dimethylcarbamoyl chloride (DMCC) is a reagent for transferring a dimethylcarbamoyl group to alcoholic or phenolic hydroxyl groups forming dimethyl carbamates, usually having pharmacological or pesticidal activities. Because of its high toxicity and its carcinogenic properties shown in animal experiments and presumably also in humans, dimethylcarbamoyl chloride can only be used under stringent safety precautions.

References

  1. "Reclazepam". Pscyhotropics.dk. 20 January 1986. Retrieved 24 August 2009.[ dead link ]
  2. US 4208327,Yonan PK,"5-Aryl-1-(2-oxazolin-2-yl)-1H-1,4-benzodiazepines and related compounds",issued 17 June 1980, assigned to GD Searle LLC.
  3. Speziale AJ, Smith LR (April 2003). "α‐Chloroacetyl Isocyanate: Isocyanic acid, anhydride with chloroacetic acid". Organic Syntheses. 46: 16. doi:10.1002/0471264180.os046.05.
  4. US 3144439,Reeder E, Sternbach LH,"Process for production of benzodiazepines",issued 1964, assigned to Hoffmann-La Roche Inc