Phenazepam

Last updated
Phenazepam
Phenazepam.svg
Phenazepam ball-and-stick model.png
Clinical data
Trade names see below
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral, IM, IV
ATC code
Legal status
Legal status
  • AU:Unscheduled
  • BR: Class B1 (Psychoactive drugs) [1]
  • CA: Schedule IV
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class C
  • US:Unscheduled (Schedule I in Louisiana). [2] Not FDA approved.
  • (RU) Rx only [3]
Pharmacokinetic data
Bioavailability 16,7% (rat) [4]
Metabolism Hepaticaromatic oxidation and C3-hydroxylation [5]
Onset of action 1.5–4 hours
Elimination half-life 6–18 hours (active metabolite unknown)
Excretion Renal
Identifiers
  • 7-Bromo-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.207.405 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H10BrClN2O
Molar mass 349.61 g·mol−1
3D model (JSmol)
  • c1ccc(c(c1)C2=NCC(=O)Nc3c2cc(cc3)Br)Cl
  • InChI=1S/C15H10BrClN2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20) Yes check.svgY
  • Key:CGMJQQJSWIRRRL-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)

Phenazepam (also known in Russia as bromdihydrochlorphenylbenzodiazepine) is a benzodiazepine drug, first developed in the Soviet Union in 1975, [6] and now produced in Russia and several other countries.

Contents

Phenazepam is used in the treatment of various mental disorders such as psychiatric schizophrenia and anxiety. It can be used as a premedication before surgery as it augments the effects of anesthetics. Recently,[ when? ] phenazepam has gained popularity as a recreational drug; misuse has been reported in the United Kingdom, [7] Finland, [8] Sweden, [9] and the United States. [10] [11]

Indications

Usually, a course of treatment with phenazepam should not normally exceed 2 weeks (in some cases therapy may be prolonged for up to 2 months) due to the risk of drug abuse and dependence. To prevent withdrawal syndrome, it is necessary to reduce the dose gradually. [12]

Chemistry

Phenazepam is a drug of the benzodiazepine class. Benzodiazepine drugs contain a benzene ring fused to a diazepine ring, which is a seven membered ring with the two nitrogen constituents located at R1 and R4. The benzyl ring of phenazepam is substituted at R7 with a bromine group. Like most benzodiazepines, phenazepam has a phenyl ring in R5 which is substituted by chlorine in the R2' group. Phenazepam also contains an oxygen group double bonded to R2 of its diazepine ring to form a ketone. This oxygen substitution at R2 is shared with other benzodiazepine drugs with the suffix -azepam.

Like other benzodiazepines, phenazepam (7-bromo-5-(2-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one) is composed of a benzene ring fused to a seven-membered 1,4-diazepine ring. A 2-chlorophenyl ring is attached at the 5-position and a bromine is attached at the 7-position. Phenazepam has a molecular formula of C15H10BrClN2O and a molecular weight of 349.6 g/mol. [13] [14]

Side effects

Side effects include hiccups, dizziness, loss of coordination and drowsiness, along with anterograde amnesia which can be quite pronounced at high doses. [15] As with other benzodiazepines, in case of abrupt discontinuation following prolonged use, severe withdrawal symptoms may occur including restlessness, anxiety, insomnia, seizures, convulsions and death, though because of its intermediate half-life [16] [17] [18] as well as that of its active metabolites, these withdrawal symptoms may take two or more days to manifest.

Contraindications and special caution

Benzodiazepines require special precaution if used in the elderly, during pregnancy, in children, alcohol or drug-dependent individuals and individuals with comorbid psychiatric disorders. [19]

Phenazepam should not be taken with alcohol or any other CNS depressants. Phenazepam should not be used therapeutically for periods of longer than one month including tapering on and off the drug as recommended for any benzodiazepine in the British national formulary. Some patients may require longer term treatment.

Phenazepam was found to be a component in some "herbal incense" mixtures in Australia and New Zealand in 2011, namely "Kronic". The particular product variety was withdrawn from the market shortly after and replaced with a new formulation. [20]

Synthesis

First, 2-(o-chlorobenzoylamino)-5-bromo-2-chlorobenzophenone is prepared by acylation of p-bromoaniline with o-chlorobenzoic acid acyl chloride in the presence of a zinc chloride catalyst. This is hydrolysed with aqueous sulfuric acid to yield 2-amino-5-bromo-2'-chlorobenzophenone, which is then acylated with hydrochloride of aminoacetic acid acyl chloride in chloroform to form 2-(aminomethylkarbonylamino)-5-bromo-2-chlorobenzophenone hydrochloride, which is converted to a base with aqueous ammonia and then thermally cyclized to bromodihydrochlorophenylbenzodiazepine (phenazepam).

Hydrochloride of aminoacetic acid acyl chloride is prepared by chemical treating glycine with phosphorus pentachloride (PCl5) in chloroform. [21]

Phenazepam sythesis (USSR).png

This method of Phenazepam synthesis was developed in the 1970s at the Physico-Chemical Institute of the Academy of Sciences of the Ukrainian SSR. [21]

Detection in biological fluids

Phenazepam may be measured in blood or plasma by chromatographic methods. Blood phenazepam concentrations are typically less than 30 μg/L during therapeutic usage, but have frequently been in the 100–600 μg/L range in automotive vehicle operators arrested for impaired driving ability. [22]

China

As of October 2015, phenazepam is a controlled substance in China. [23]

United States

Under federal United States law, phenazepam is not currently classified as a controlled substance, as the Federal Analog Act only provides for automatic assumed classification of chemicals "substantially similar" to existing Schedule I or Schedule II drugs, whereas all controlled benzodiazepines under the Controlled Substances Act are classified as Schedule IV. Although phenazepam is currently not controlled, sale for human use remains illegal in the United States. [24] Suppliers attempt to circumvent this regulation by placing a "Not for human use" disclaimer on the product's label.

Individual states in the United States often ban these analog drugs by name as they appear. Since 2012, Louisiana has classified phenazepam as a controlled dangerous substance. [25] This ban affects several products, some of which were sold at retail stores under the guise of air freshener or similar, containing phenazepam yet claiming not to be for human use. This legislation was introduced after one such product, branded as "Zannie" and marketed as an air freshener rapidly gained publicity as the subject of numerous media reports, attracting the attention of officials. [26] The ensuing investigation effort, led by Senator Fred Mills and Louisiana Poison Center Director Mark Ryan, positively identified the active ingredient of "Zannie" as phenazepam. According to Ryan, chemical analysis identified the active ingredient as "100 percent phenazepam". [25]

Paul Halverson, director and state health officer for the Arkansas Department of Health, approved an emergency rule to ban the sale and distribution of phenazepam shortly after the Louisiana ban.

Alabama made Phenazepam a schedule I substance on March 18th, 2014. [27]

United Kingdom

Phenazepam is a class C drug in the UK. [28]

The UK home office banned importation of phenazepam on Friday 22 July 2011 [29] while it drafted legislation, released in January 2012 [30] to become law at the end of March 2012. [31] The bill was quashed following advice from the ACMD as it included two non-abusable steroids. [32] There was a new discussion about its fate on April 23, 2012, where it was decided that the bill would be rewritten and phenazepam would still be banned. [33]

It was eventually banned on June 13, 2012 as a class C, schedule II drug. [34]

Elsewhere

Phenazepam was classified as a narcotic in Finland in July, 2014. [35]

Phenazepam is considered a narcotic in Norway, as per a March 23, 2010 Health Department addition to the Regular Narcotic List.

In Russia, phenazepam is a controlled substance since March 22, 2021. [36]

In Estonia, phenazepam is a Schedule IV substance under the Narcotic Drugs and Psychotropic Substances Act.[ citation needed ] Schedule IV is the lowest classification of psychoactive substances in Estonia. It includes prescribable drugs, including other benzodiazepines.

UN Single Convention on Narcotic Drugs

On 8 March 2016 at its 59th Session, the Commission on Narcotic Drugs (CND) added Phenazepam to relevant schedules of the Convention on Psychtropic Substances of 1971. [37]

Trade names

RU :

See also

Related Research Articles

<span class="mw-page-title-main">Benzodiazepine</span> Class of depressant drugs

Benzodiazepines, colloquially called "benzos", are a class of depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed to treat conditions such as anxiety disorders, insomnia, and seizures. The first benzodiazepine, chlordiazepoxide (Librium), was discovered accidentally by Leo Sternbach in 1955, and was made available in 1960 by Hoffmann–La Roche, which followed with the development of diazepam (Valium) three years later, in 1963. By 1977, benzodiazepines were the most prescribed medications globally; the introduction of selective serotonin reuptake inhibitors (SSRIs), among other factors, decreased rates of prescription, but they remain frequently used worldwide.

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

Diazepam, sold under the brand name Valium among others, is a medicine of the benzodiazepine family that acts as an anxiolytic. It is used to treat a range of conditions, including anxiety, seizures, alcohol withdrawal syndrome, muscle spasms, insomnia, and restless legs syndrome. It may also be used to cause memory loss during certain medical procedures. It can be taken orally, as a suppository inserted into the rectum, intramuscularly, intravenously or used as a nasal spray. When injected intravenously, effects begin in one to five minutes and last up to an hour. When taken by mouth, effects begin after 15 to 60 minutes.

<span class="mw-page-title-main">Temazepam</span> Insomnia medication

Temazepam, sold under the brand name Restoril among others, is a medication of the benzodiazepine class which is generally used to treat severe or debilitating insomnia. It is taken by mouth. Temazepam is rapidly absorbed, and significant hypnotic effects begin in less than 30 minutes and can last for up to eight hours. Prescriptions for hypnotics such as temazepam have seen a dramatic decrease since 2010, while anxiolytics such as alprazolam, clonazepam, and lorazepam have increased or remained stable. Temazepam and similar hypnotics, such as triazolam (Halcion) are generally reserved for severe and debilitating insomnia. They have largely been replaced by z-drugs and atypical antidepressants as first line treatment for insomnia.

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

Alprazolam, sold under the brand name Xanax and others, is a fast-acting, potent tranquilizer of moderate duration within the triazolobenzodiazepine group of chemicals called benzodiazepines. Alprazolam is most commonly prescribed in the management of anxiety disorders, especially panic disorder and generalized anxiety disorder (GAD). Other uses include the treatment of chemotherapy-induced nausea, together with other treatments. GAD improvement occurs generally within a week. Alprazolam is generally taken orally.

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

Lorazepam, sold under the brand name Ativan among others, is a benzodiazepine medication. It is used to treat anxiety, trouble sleeping, severe agitation, active seizures including status epilepticus, alcohol withdrawal, and chemotherapy-induced nausea and vomiting. It is also used during surgery to interfere with memory formation and to sedate those who are being mechanically ventilated. It is also used, along with other treatments, for acute coronary syndrome due to cocaine use. It can be given orally, transdermally, intravenously (IV), or intramuscularly When given by injection, onset of effects is between one and thirty minutes and effects last for up to a day.

<span class="mw-page-title-main">Midazolam</span> Benzodiazepine used for anesthesia and procedural sedation

Midazolam, sold under the brand name Versed among others, is a benzodiazepine medication used for anesthesia, premedication before surgical anesthesia, and procedural sedation, and to treat severe agitation. It induces sleepiness, decreases anxiety, and causes anterograde amnesia.

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

Nimetazepam is an intermediate-acting hypnotic drug which is a benzodiazepine derivative. It was first synthesized by a team at Hoffmann-La Roche in 1964. It possesses powerful hypnotic, anxiolytic, sedative, and skeletal muscle relaxant properties. Nimetazepam is also a particularly potent anticonvulsant. It is marketed in 5 mg tablets known as Erimin, which is the brand name manufactured and marketed by the large Japanese corporation Sumitomo. Japan is the sole manufacturer of nimetazepam in the world. Outside of Japan, Erimin is available in much of East and Southeast Asia and was widely prescribed for the short-term treatment of severe insomnia in patients who have difficulty falling asleep or maintaining sleep. Sumitomo has ceased manufacturing Erimin since November 2015. It is still available as a generic drug or as Lavol.

<span class="mw-page-title-main">Adinazolam</span> Triazolobenzodiazepine drug

Adinazolam is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It possesses anxiolytic, anticonvulsant, sedative, and antidepressant properties. Adinazolam was developed by Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed. Adinazolam was never FDA approved and never made available to the public market; however, it has been sold as a designer drug.

<span class="mw-page-title-main">Etizolam</span> Benzodiazepine analog drug

Etizolam is a thienodiazepine derivative which is a benzodiazepine analog. The etizolam molecule differs from a benzodiazepine in that the benzene ring has been replaced by a thiophene ring and triazole ring has been fused, making the drug a thienotriazolodiazepine.

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

Brotizolam is a sedative-hypnotic thienotriazolodiazepine drug which is a benzodiazepine analog. It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties, and is considered to be similar in effect to other short-acting hypnotic benzodiazepines such as triazolam or midazolam. It is used in the short-term treatment of severe insomnia. Brotizolam is a highly potent and short-acting hypnotic, with a typical dose ranging from 0.125 to 0.25 milligrams, which is rapidly eliminated with an average half-life of 4.4 hours.

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

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<span class="mw-page-title-main">Codeine</span> Opiate and prodrug of morphine used to treat pain

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

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<span class="mw-page-title-main">Mephedrone</span> Synthetic stimulant drug

Mephedrone, also known as 4-methylmethcathinone, 4-MMC, and 4-methylephedrone, is a synthetic stimulant drug of the amphetamine and cathinone classes. Slang names include drone, M-CAT, White Magic, meow meow and bubble. It is chemically similar to the cathinone compounds found in the Khat plant of eastern Africa. It comes in the form of tablets or crystals, which users can swallow, snort or inject, producing effects similar to those of MDMA, amphetamines and cocaine.

<span class="mw-page-title-main">6-APB</span> Psychoactive drug

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<span class="mw-page-title-main">Methoxetamine</span> Dissociative drug

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

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<span class="mw-page-title-main">Flubromazolam</span> Triazolobenzodiazepine drug

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<span class="mw-page-title-main">Bromazolam</span> Triazolobenzodiazepine

Bromazolam (XLI-268) is a triazolobenzodiazepine (TBZD) which was first synthesised in 1976, but was never marketed. It has subsequently been sold as a designer drug, first being definitively identified by the EMCDDA in Sweden in 2016. It is the bromo instead of chloro analogue of alprazolam and has similar sedative and anxiolytic effects to it and other benzodiazepines. Bromazolam is a non subtype selective agonist at the benzodiazepine site of GABAA receptors, with a binding affinity of 2.81 nM at the α1 subtype, 0.69 nM at α2 and 0.62 nM at α5. The "common" dosage range for users of bromazolam was reported to be 1–2 mg, suggesting its potency is similar to alprazolam.

<span class="mw-page-title-main">Flualprazolam</span> Triazolobenzodiazepine drug

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