Nitrazolam

Last updated
Nitrazolam
Nitrazolam.svg
Legal status
Legal status
Identifiers
  • 1-methyl-8-nitro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C17H13N5O2
Molar mass 319.324 g·mol−1
3D model (JSmol)
  • Cc1nnc2CN=C(c3ccccc3)c4cc(ccc4n12)[N+]([O-])=O
  • InChI=1S/C17H13N5O2/c1-11-19-20-16-10-18-17(12-5-3-2-4-6-12)14-9-13(22(23)24)7-8-15(14)21(11)16/h2-9H,10H2,1H3
  • Key:OYRPNABWTHDOFK-UHFFFAOYSA-N

Nitrazolam is a triazolobenzodiazepine (TBZD) , which are benzodiazepine (BZD) derivatives, [1] that has been sold online as a designer drug. [2] [3]

Contents

It is closely related to clonazolam or flunitrazolam, only differing by the removal of a chlorine or fluorine group respectively at the benzene ring.

A study in mice indicated that nitrazolam can be several times more potent than diazepam as an antagonist of electroshock-induced tonic-extensor convulsions but less potent than diazepam at preventing the righting reflex. [4]

Nitrazolam has been used as an example compound to demonstrate the microscale synthesis of reference materials utilizing polymer‐supported reagents. [5]

United Kingdom

In the UK, nitrazolam has been classified as a Class C drug by the May 2017 amendment to The Misuse of Drugs Act 1971 along with several other designer benzodiazepine drugs. [6]

See also

Related Research Articles

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

Alprazolam, sold under the brand name Xanax, is a fast-acting, potent tranquilizer of moderate duration within the triazolobenzodiazepine group of chemicals called benzodiazepines. Alprazolam is most commonly used in management of anxiety disorders, specifically panic disorder or 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.

Thailand's Psychotropic Substances Act is a law designed to regulate certain mind-altering drugs. According to the Office of the Narcotics Control Board, "The Act directly resulted from the Convention on Psychotropic Substances 1971 of which Thailand is a party." The Act divides psychotropic drugs into four Schedules. Offenses involving Schedule I and II drugs carry heavier penalties than those involving Schedule III and IV drugs. Note that this statute does not regulate most opioids, cocaine, or some amphetamines. The vast majority of narcotic painkillers, along with cocaine and most amphetamines are regulated under the Narcotics Act.

<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> Chemical compound

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> Chemical compound

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">Zapizolam</span> Chemical compound

Zapizolam is a pyridodiazepine drug, which is a benzodiazepine analog of pyridotriazolodiazepine group. It has sedative and anxiolytic effects similar to those produced by benzodiazepine derivatives, and has been sold illicitly as a designer drug.

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

Meclonazepam ((S)-3-methylclonazepam) was discovered by a team at Hoffmann-La Roche in the 1970s and is a drug which is a benzodiazepine derivative similar in structure to clonazepam. It has sedative and anxiolytic actions like those of other benzodiazepines, and also has anti-parasitic effects against the parasitic worm Schistosoma mansoni.

<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">Diclazepam</span> Benzodiazepine medication

Diclazepam (Ro5-3448), also known as chlorodiazepam and 2'-chloro-diazepam, is a benzodiazepine and functional analog of diazepam. It was first synthesized by Leo Sternbach and his team at Hoffman-La Roche in 1960. It is not currently approved for use as a medication, but rather sold as an unscheduled substance. Efficacy and safety have not been tested in humans.

<span class="mw-page-title-main">Flubromazepam</span> Benzodiazepine designer drug

Flubromazepam is a benzodiazepine derivative which was first synthesized in 1960, but was never marketed and did not receive any further attention or study until late 2012 when it appeared on the grey market as a novel designer drug.

<span class="mw-page-title-main">Clonazolam</span> Benzodiazepine derivative research chemical

Clonazolam is a drug of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. Little research has been done about its effects and metabolism, and is sold online as a designer drug.

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

Flubromazolam (JYI-73) is a triazolobenzodiazepine (TBZD), which are benzodiazepine (BZD) derivatives. Flubromazolam is reputed to be highly potent, and concerns have been raised that clonazolam and flubromazolam in particular may pose comparatively higher risks than other designer benzodiazepines, due to their ability to produce strong sedation and amnesia at oral doses of as little as 0.5 mg. Life-threatening adverse reactions have been observed at doses of only 3 mg of flubromazolam.

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

Deschloroetizolam is a thienotriazolodiazepine that is the dechlorinated analog of the closely related etizolam. The compound has been sold as a designer drug.

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

Triazolobenzodiazepines (TBZD) are a class of benzodiazepine (BZD) derivative pharmaceutical drugs. Chemically, they differ from other benzodiazepines by having an additional triazole ring fused to the diazepine ring. The triazole and diazepine rings share a nitrogen atom.

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

Flualprazolam is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It was first synthesised in 1976, but was never marketed. It can be seen as the triazolo version of fludiazepam. It has subsequently been sold as a designer drug, first being definitively identified as such in Sweden in 2018. It can be described as the 2'-fluoro derivative of alprazolam or the fluoro instead of chloro analogue of triazolam, and has similar sedative and anxiolytic effects.

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

Phenazolam, is a benzodiazepine derivative which acts as a potent sedative and hypnotic drug. It was first invented in the early 1980s, but was never developed for medical use. It has been sold over the internet as a designer drug, first being identified in seized samples by a laboratory in Sweden in March 2016.

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

Fluadinazolam is a benzodiazepine derivative developed in 1973, with sedative and anxiolytic effects. It is a derivative of the never commercially marketed benzodiazepine adinazolam and has similarly been sold as a designer drug.

<span class="mw-page-title-main">Flubrotizolam</span> Thienotriazolodiazepine

Flubrotizolam is a thienotriazolodiazepine derivative with potent sedative and anxiolytic effects, which has been sold as a designer drug.

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

Fluetizolam is a thienotriazolodiazepine derivative with potent sedative and anxiolytic effects, which has been sold as a designer drug.

References

  1. Hester Jr JB (19 October 1976). "Patent US3987052 - 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines". The Upjohn Company.
  2. "Nitrazolam". New Synthetic Drugs Database.
  3. Moosmann B, Bisel P, Franz F, Huppertz LM, Auwärter V (November 2016). "Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines - an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam and nitrazolam". Journal of Mass Spectrometry. 51 (11): 1080–1089. Bibcode:2016JMSp...51.1080M. doi:10.1002/jms.3840. PMID   27535017.
  4. Hester JB, Rudzik AD, Kamdar BV (November 1971). "6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines which have central nervous system depressant activity". Journal of Medicinal Chemistry. 14 (11): 1078–81. doi:10.1021/jm00293a015. PMID   5165540.
  5. Dowling G, Kavanagh PV, Eckhardt HG, Twamley B, Hessman G, McLaughlin G, et al. (March 2018). "An approach to shortening the timeframe between the emergence of new compounds on the drugs market and the availability of reference standards: The microscale syntheses of nitrazolam and clonazolam for use as reference materials, utilizing polymer-supported reagents" (PDF). Drug Testing and Analysis. 10 (7): 1198–1208. doi:10.1002/dta.2383. PMID   29542872. S2CID   205763816.
  6. "The Misuse of Drugs Act 1971 (Amendment) Order 2017".