Buy Nitrazolam CAS NO.28910-99-8. Nitrazolam is a triazolobenzodiazepine (TBZD) , which are benzodiazepine (BZD) derivatives, that has been sold online as a designer drug.
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.
Nitrazolam has been used as an example compound to demonstrate the microscale synthesis of reference materials utilizing polymer‐supported reagents.
Nitrazolam CAS NO.28910-99-8
- Product Details
Keywords
- 28910-99-8
- Nitrazolam
- 1-methyl-8-nitro-6-phenyl-4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine
Quick Details
- ProName:Nitrazolam
- CasNo:28910-99-8
- Molecular Formula:C17H13N5O2
- Appearance:WHITE POWDER
- Application:28910-99-8
- PackAge:As required
- ProductionCapacity:10 Kilogram/Month
- Purity:98%
- LimitNum:10 Gram
Superiority
Nitrazolam ? ? ? ? ? CAS:28910-99-8 NAME: 1-methyl-8-nitro-6-phenyl-4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine; 1-methyl-8-nitro-6-phenyl-4H-s-triazolo [4,3-a][1,4] benzodiazepine; 1-Methyl-8-nitro-6-phenyl-4H-s-triazolo[4,3-a]-[1,4]benzodiazepine; 1-Methyl-6-phenyl-8-nitro-4H-s-triazolo<4,3-a><1,4>-benzodiazepin; 1-Methyl-8-nitro-6-phenyl-TABDA MF: C17H13N5O2 MW:t 319.32
Popent Benzos powder Nitrazolam CAS 28910-99-8
Chapters and Articles
You might find these chapters and articles relevant to this topic.
Benzodiazepines
Christopher P. Holstege, in Encyclopedia of Toxicology (Second Edition), 2005•
Representative Chemicals: Alprazolam; Chlordiazepoxide; Clonazepam; Clorazepate dipotassium; Clorazepate monopotassium; Diazepam; Estazolam; Flunitrazepam; Flurazepam; Halazepam; Lorazepam; Midazolam; Nitrazepam; Oxazepam; Prazepam; Quazepam; Temazepam; Triazolam•
Chemical Abstracts Service Registry Numbers: CAS 28981-97-7 (alprazolam); CAS 439-14-5 (diazepam); CAS: 604-75-1 (oxazepam)•
Synonyms:○
Alprazolam – Xanax; C17H13ClN4; 8-Chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine○
Chlordiazepoxide – Librium; C16H14ClN3O; 7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine-4-oxide○
Clonazepam – Klonopin, Rivotril, Clonapam; C15H10ClN3O3; 5-(2-Chlorophenyl)-1,3-dihydro-7-nitro-2H-1,4-benzodiazepin-2-one○
Clorazepate dipotassium – Tranxene; ClorazeCaps; ClorazeTabs; C16H11ClK2N2O4○
Clorazepate monopotassium – Azene; C16H11ClKN2O4○
Diazepam – Valium, Vivol, E-Pam; C16H13ClN2O; 7-Chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one○
Estazolam – ProSom; C16H11ClN4; 8-Chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine○
Flunitrazepam – Rohypnol; C16H12FN3O3; 5-(2-Fluorophenyl)-1,3-dihydro-1-methyl-7-nitro-2H-1,4-benzodizepin-2-one○
Flurazepam – Dalmane, Somnol, Som Pam; C12H23ClFN3O; 7-Chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one○
Halazepam – Paxipam; C17H12ClF3N2O; 7-Chloro-1,3-dihydro-5-phenyl-1-(2,2,2-trifluoroethyl)-2H-1,4-benzodiazepin-2-one○
Lorazepam – Ativan; C15H10ClN2O2; 7-Chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one○
Midazolam – Versed; C18H13ClFN3; 8-Chloro-6-(2-fluorophenyl)-1-methyl-4H-imidadazo[1,5-a][1,4]benzodiazepine○
Nitrazepam – Mogadon; C15H11N3O3; 1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one○
Oxazepam – Serax; C15H11ClN2O2; 7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one○
Prazepam – Verstran; C19H17ClN2O; 7-Chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one○
Quazepam – Doral; C17H11ClF4N2S; 7-Chloro-5-(2-fluorophenyl)-1,3-dihydro-1-(2,2,2-trifluoroethyl)-2H-1,4-benzodiazepine-2-thione○
Temazepam – Restoril; 3-Hydroxydiazepam; C6H13ClN2O2; 7,-Chloro-l,3-dihydro-3-hydroxy-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one○
Triazolam – Halcion; C17H12Cl2N4; 8-Chloro-6-(2-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine•
Chemical/Pharmaceutical/Other Class: 5-Aryl-1,4-benzodiazepines•
Chemical Structure:
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Individual Analytes, Specimen Handling, Stability, and Other Issues
Robert M. WhiteSr., Christine M. Moore, in Detection of Drugs and Their Metabolites in Oral Fluid, 2018
Benzodiazepines
As a class of compounds, the 1,4-benzodiazepines are pharmacodynamically potent but chemically unstable. They demonstrate pH, light, and oxidation sensitivity. Perhaps, the only two stable ones for immunoassay calibration and control are nitrazepam (not approved for use in the United States) and nordiazepam (metabolite of diazepam).
The amino-metabolites of flunitrazepam, nitrazepam, and clonazepam are present at higher concentration and are more stable than the parent drugs in oral fluid.21 From 1001 samples positive for clonazepam and its main metabolite 7-aminoclonazepam, both were detected in 70.6%, only clonazepam in 6.3%, and only the metabolite in 23% of the specimens. For nitrazepam the numbers were similar: both drug and metabolite were present in 65.8% of specimens, the parent drug only in 7.5%, and metabolite only in 26.5%.22
Six-membered Rings with One Heteroatom and Fused Carbocyclic Derivatives
Marudai Balasubramanian, James G. Keay, in Comprehensive Heterocyclic Chemistry II, 1996
5.06.8.22 CNS Stimulants
Zopiclone (293) 〈73GEP(O)2300491〉, derived from 2-amino-5-chloropyridine and used as a CNS drug 〈90MI 506-03〉, is the first of a family of nonbenzodiazepines which show a pharmacological profile similar to chlordiazepoxide and nitrazepam. Linopirdine (294), an orally active cognitive enhancer targeted to ameliorate deficiencies associated with Alzheimer’s disease by stimulating CNS neurotransmitter release (such as acetylcholine, dopamine, and serotonin), is obtained by the alkylation of 1-phenyloxindole using two equivalents of 4-picolyl chloride hydrochloride under phase transfer conditions 〈93SC1617〉. 9-Amino-1,2,3,4-tetrahydroacridine (295) is used for the treatment of Alzheimer’s disease and is also an acetylcholinesterase inhibitor 〈87MI 506-04, 90MI 506-04, 91MI 506-04〉. The piperidine derivatives methylphenidate (296) 〈44HCA1748〉 and pipradrol (297) are used as CNS stimulants 〈48JA4001, 53USP2624739〉.
The use of magnetic nanoparticles in sample preparation devices and tools
Rüstem Keçili, … Chaudhery Mustansar Hussain, in Handbook of Nanomaterials in Analytical Chemistry, 2020
5.4.3 Magnetic solid-phase extraction for biological samples
MSPE for biological samples (i.e., blood plasma, urine, etc.) is another crucial application area of magnetic nanoparticles. In a study carried out by Heidari and Limouei-Khosrowshahi [88], magnetic Fe3O4 nanoparticles modified with carbon were prepared for the extraction of various pharmaceutical compounds including carvedilol, losartan, and amlodipine besylate from plasma samples. In this study, the detection limit values varied in the range between 0.09 and 0.69 ng mL−1.
In another important work [89], Asgharinezhad et al. developed magnetic nanocomposite composed of Fe3O4 nanoparticles and polyaniline. The developed magnetic nanocomposite was successfully applied for the efficient extraction of benzodiazepine drugs including nitrazepam and lorazepam from human plasma and urine samples. The schematic depiction of the extraction process for the target drugs from biological samples using magnetic nanocomposites is shown in Fig. 5.6. The detection limit values for nitrazepam and lorazepam were obtained in the range from 0.5 to 1.8 µg L−1 and 0.2 to 2.0 µg L−1, respectively.
Feng and colleagues reported the design and preparation of Fe3O4 nanoparticle-modified multi-walled carbon nanotubes (MWCNTs) [90]. The prepared MWCNT-based nanocomposites were successfully used for the efficient extraction of brucine (a neurotoxic alkaloid existing in the Nux-vomica tree) from human urine samples. In their study, the detection limit and quantification limit values were achieved as 6 and 21 ng mL−1, respectively.
In another interesting study conducted by Chen and coworkers [91], magnetic Fe3O4 nanoparticles having a layer composed of 1,3,5-triformylbenzene(Tb) and benzidine (Bd) (Fe3O4@TbBd) were prepared and successfully applied for the selective extraction of seven estrogens from human urine samples. The schematic demonstration of the preparation of magnetic Fe3O4@TbBd nanocomposite and extraction process for the target estrogens is shown in Fig. 5.7. In this study, the achieved detection limit values varied in the range from 0.2 to 7.7 ng L−1.
Mirzapour et al. reported the preparation of organic dendrimer-modified magnetic Fe3O4 nanoparticles for the efficient extraction of rosuvastatin from human urine, blood plasma, and tablet samples [92]. For this purpose, first, magnetic Fe3O4 nanoparticles were synthesized by using FeCl2 and FeCl3. Then the surface of the synthesized magnetic Fe3O4 nanoparticles was modified with organic dendrimers containing ethylene diamine and methyl methacrylate. The prepared organic dendrimer-modified magnetic Fe3O4 nanoparticles were successfully used for the extraction of the target pharmaceutical compound rosuvastatin from human urine, blood plasma, and tablet samples. In this study, the highest extraction capacity of the prepared organic dendrimer-modified magnetic Fe3O4 nanoparticles was achieved as 61 mg g−1.
In another study reported by Ji and colleagues [93], magnetic Fe3O4 nanoparticles having MIP layer were successfully prepared and applied for the selective extraction of 9-hydroxyrisperidone and risperidone from human urine samples. The obtained detection limit values for 9-hydroxyrisperidone and risperidone were 0.24 and 0.21 ng mL−1, respectively.
Azodi-Deilami and coworkers prepared magnetic Fe3O4 nanoparticles coated with molecularly imprinted polymeric shell for the selective extraction of paracetamol from human plasma samples [94]. In their study, the detection limit and quantification limit values for the target pharmaceutical compound paracetamol in human plasma were achieved as 0.17 and 0.4 μg L−1, respectively.
In another interesting study [95], Jiang et al. reported the development of magnetic Fe3O4@SiO2 nanoparticles modified with octadecyl (C18) functional groups for the efficient extraction of aromatic amines including 1-aminonaphthalene, 4-aminobiphenyl, 4,4ʹ-diaminodiphenylmethane and 4-aminophenylthioether from human urine samples. The detection limit values for 1-aminonaphthalene, 4-aminobiphenyl, 4,4ʹ-diaminodiphenylmethane, and 4-aminophenylthioether were obtained as 1.3, 0.88, 1.1, and 1.1 ng mL−1, respectively.
Zhang and colleagues prepared polydopamine-coated magnetic Fe3O4 nanoparticles modified with MWCNTs for the extraction of antiepileptic drugs including phenytoin, oxcarbazepine, and carbamazepine from human urine, plasma, and cerebrospinal fluid samples [96]. In their study, the achieved detection limit values for the target drug compounds were in the range between 0.4 and 3.1 ng mL−1.Read more
Liquid Chromatography | Clinical Applications☆
C. Ialongo, … E. Camera, in Encyclopedia of Analytical Science (Third Edition), 2019
Benzodiazepines
The BDZ drugs are a broad class of > 30 compounds acting as positive allosteric modulators of the GABAA-chloride channel of neurons whereby they produce sedation, hypnosis, anxiolysis, as well as muscle relaxation alongside anticonvulsant action. Pharmacologically, they are known to develop tolerance and induce dependence after prolonged administration. Due to this spectrum of actions BDZs are widespread drugs of abuse.29,30 They all share the heterocyclic backbone with the condensed diazepinic and benzenic rings. BDZs can be subgrouped into six classes based on the sidechain substitution: (a) 2-keto-BDZ: diazepam (DZP) and chlordiazepoxide (CDZ); (b) 3-hydroxy-BDZ: lorazepam (LZP), oxazepam (OXZ), and temazepam (TMZ); (c) 7-nitro-BDZ: clonazepam (CLZ) and nitrazepam (NTZ); (d) triazolo-BDZ: triazolam (TZL) and alprazolam (AZL); (e) imidazo-BDZ: midazolam (MDZ); (f) 2-thione-BDZ: quazepam (QZP).
Almost all the BDZs are substrates of hepatic cytochromes, undergoing hydroxylation, reduction or N-dealkylation. After the phase I biotransformation, BDZs are conjugated with glucuronic acid and excreted with urines, although small amount of free drug can be detected. Noteworthy, some metabolites retain the pharmacological activity of the parental drug but showing different potency and pharmacokinetics (e.g., half-life). By virtue of their retained pharmcological activity, metabolites are used and commercialized as BDZ drugs by themselves. For instance, the brand names Valium, Restoril, and Serax correspond to the DZP, its metabolite TMZ and the TMZ metabolite OXZ, respectively.
The testing of BDZs can be carried out in either plasma or urines; the former one is useful for the assessment of recent consumption, whereas the latter one is exploited to track past exposure. Historically, confirmatory analysis has been performed on urine samples with GC-MS using enzymatic hydrolysis of the glucuronide conjugates followed by derivatization. The range of polarity of BDZs is rather broad since some of the active compounds are hydrophilic metabolites as mentioned earlier. Alkalinization of plasma with ammonia solution followed by LLE with strong organic solvent can be carried out to estract BDZs successfully from biofluids. Alternatively, SPE based on mixed-phase bed (like the Oasis HLB already described) is suitable and amenable for the on-line semi-automated sample clean up by means of the switching-valve technique.
The broad polarity of BDZs also affects the chromatography where a pure C18 stationary phase offers poor retention to more polar compounds. Therefore, the aqueous-capable C18 stationary phase combined with mobile phases with properly adjusted pH are recommended. Optimized gradient elution allows the resolution of up to 30 BDZs residues within 10 min. ESI + and APCI + are comparably effective in the ionization of BDZs before MS detection. However, if the mobile phase pH is kept basic (e.g., pH = 9) the APCI + shows more efficient formation of BDZ-proton adduct; besides, background noise and ion suppression are minimized at higher pH. MRM transitions of representative BDZs are reported in Table 4.
Table 4. Typical APCI +/MRM of most representative BDZs
| Compound | Precursor iona | Product ion 1 | Product ion 2 | Product ion 3 |
|---|---|---|---|---|
| DZP | 285 | 193 | 154 | 222 |
| CDZ | 300 | 282 | 227 | 283 |
| LZP | 321 | 275 | 229 | 303 |
| OXZ | 287 | 241 | 269 | 104 |
| TMZ | 301 | 255 | 283 | 177 |
| CLZ | 316 | 270 | 214 | 302 |
| NTZ | 282 | 236 | 180 | 207 |
| TZL | 343 | 239 | 308 | 315 |
| AZL | 309 | 281 | 205 | 274 |
| MDZ | 326 | 291 | 249 | 222 |
| QZP | 387 | 258 | 324 | 247 |
am/z of [M + NH4]+ ion.
For quantitative purposes, the use of at least one deuterated reference compound for each chemical class of BDZ drugs is advisable. Noteworthy, in some cases it is preferable to use an IS also for the specific metabolite if its recovery and/or ionization efficiency is expected to differ substantially from its parental drug. For instance, the solubility of MDZ depends strongly on pH while the solubility of its major and active alpha-hydroxylated metabolite does not. Such a difference strongly affects recovery of the two compounds.
Nowadays CE-IVD kits are marketed for BDZs. Some of the commercially available kits extend the quantitation to other psychoactive drugs like the pharmacologically similar “Z-drugs.”Read more
Five-membered Rings with One Heteroatom and Fused Carbocyclic Derivatives
Ronald K. Russell, Jeffery B. Press, in Comprehensive Heterocyclic Chemistry II, 1996
2.12.3.1 CNS Agents
A preponderance of reports of biologically active thiophene derivatives arises in the area of CNS research. In the area of antipsychotic (neuroleptic) therapy, olanzepine (12) is nearing NDA submission as a therapeutic agent with reduced extrapyramidal side-effects (EPS) similar in profile to clozapine. Studies of conformational restriction of thieno[2,3-b][1,5]benzodiazepine analogues of (12) show that antidopaminergic and anticholinergic activities of the series are modulated by steric interference with the piperazine ring 〈82JMC1133〉. A number of thieno[3,2-b][1,5]benzoxazepine and -benzothiazepine derivatives, the thiophene positional isomers of (12), were made as analogues of clozapine. 7-Chloro substitution on these derivatives reduces propensity for undesired EPS 〈92AF896〉. The taclamine thiophene analogue (13), QM-7184, has interesting neuroleptic activity while also producing α-adrenergic blockade. Although (13) is less potent than typical neuroleptic drugs such as haloperidol, its effects on the adrenergic system are speculated to be particularly interesting for further study in schizophrenia 〈83AF1417〉. SKF 89145 (14) was discovered as a part of a program investigating selective D1 agonists 〈87MI 212-02, 87MI 212-03〉. Careful studies of (14) and its thiophene isomer SKF 89641 show it is a partial D1 agonist with greater efficacy than the benzene isostere 〈89MI 212-02〉.
Etizolam (15) was approved for use by Yoshitomi in 1984 with an antianxiety (anxiolytic) therapeutic profile similar to that of diazepam. Studies of the behavioral effects of brotizolam (16) suggest that it has anxiolytic effects with potency between that of diazepam and nitrazepam 〈84MI 212-02〉. These effects include antagonism of pentylenetetrazol-induced convulsions and electroshock seizures as well as sleep potentiation 〈84MI 212-03〉. Compound (16) is effective at improving poor sleep induced by high altitude 〈84MI 212-04〉. Nonbenzodiazepine derivatives also have anxiolytic potential. A series of thienylpyrazoloquinoline derivatives shows that (17) and its isostere have equal affinity for the benzodiazepine (BZ) receptor but that they cause opposite behavioral effects. This phenomenon is postulated to result from inverse agonism at the receptor 〈88JMC1738〉. Of a series of benzothieno[2,3-c]pyridines, AP159 (18) is among the most potent in anticonflict and memory impairment behavioral assays. Despite its bioisosterism with β-carbolines, (18) binds not to BZ but rather to 5-HT1A receptors 〈90JMC3110〉. Only the (R)-isomers of these derivatives selectively bind to the 5-HT1A receptor 〈93JMC3526〉. The BZ receptor is an allosteric regulatory site of the γ-aminobutyric acid (GABA) receptor. 3-Aryl-GABA congeners are specific ligands for bicuculline-insensitive GABAB receptors. The racemic β-heteroyl-GABA analogue (19) is a particularly effective ligand 〈91JMC2557〉. Derivative (19) antagonizes ileal GABAB receptors but is a full agonist at central receptors 〈92MI 212-01〉 and discriminates between GABAA and GABAB sites 〈93MI 212-02〉. Identification of a novel class of GABA uptake inhibitors has led to the developmental candidate, tiagabine (20), as an anticonvulsant 〈93JMC1716〉.
Compound (21) (T-588) is a cerebral activator with effects on normobaric hypoxia, KCN-induced anoxia, and ischemia 〈93MI 212-03〉. Activation of the CNS cholinergic system is at least one of the mechanisms of action of (21). Compound 8319 (22) is a novel noncompetitive N-methyl-d-aspartic acid (NMDA) antagonist and has neuroprotective and anticonvulsant properties in preclinical biological screens 〈90MI 212-01〉. A series of 2-amino-3-benzoylthiophene derivatives were prepared as adenosine A1 agonists, of which PD 81,723 (23) was the most interesting 〈90MI 212-02〉. Thiophene analogues of the local anesthetic lotucaine such as (24) also have platelet antiaggregatory properties 〈87FES267〉. Derivative S-14671 (25) is an exceptionally potent 5-HT1A antagonist with 5-HT1C antagonist properties 〈91MI 212-02〉. Sulfentanil (26) is a narcotic analgesic with greater potency and better therapeutic ratio than fentanyl; it was first marketed in the mid-1980s. SAR studies of (26) examining effects of replacing the methoxy moiety with varying acyl groups have been reported 〈89JMC968〉. The 2-thiophenecarboxamide derivative (27) as well as its 3-isomer have high μ-opioid vs. δ-opioid selectivity 〈92MI 212-02〉.
As part of an extensive study of phencyclidine (PCP), which is one of the most widely abused CNS drugs, the thiophene isostere (TCP, (28)) has become the preferred ligand for characterization of the PCP-binding site. Continuation of these studies has shown that cis(29) is an NMDA receptor antagonist which is similar to TCP in affinity for the PCP binding site and 38-fold more potent than the trans-isomer 〈91CPB1581〉. The benzo[b]thiophene isostere of PCP (BTCP, GK13, (30)) is a noncompetitive NMDA antagonist and a potent dopamine (DA) uptake inhibitor but has low affinity for the PCP receptor 〈89MI 212-03〉. Isocyanate (31) is the most efficient alkylating agent of a series of irreversible affinity ligands for the PCP recognition site of the NMDA receptor 〈92MI 212-03〉. [3H]-(28) labels two affinity binding sites in the human cortex 〈91MI 212-03, 86MI 212-01〉. [3H]-(30) also binds to two brain sites and further study shows that PCP interacts with DA-uptake sites but that these sites are not the PCP receptor 〈88MI 212-02〉. Some molecular modeling investigations led to the synthesis of several piperazine analogues of (30) which have high binding affinity 〈93EJM893〉. Other replacements for the piperidine moiety of (28) include pyrrolidine and morpholine derivatives 〈88MI 212-03〉. Several papers discuss the synthesis and biological evaluation of homologues of (30) at dopamine-uptake, PCP- and σ-binding sites 〈93JMC1188, 93JMC4075〉.
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Drugs of Abuse☆
Niamh NicDaéid, Craig McKenzie, in Encyclopedia of Analytical Science (Third Edition), 2019
Synthetic Drugs
Amphetamine and Amphetamine-Type-Stimulants (ATS)
After cannabis, ATS are the most commonly abused drugs globally. From a chemical point of view all amphetamine-type stimulants are related to β-phenethylamine which is the basic element of the neurotransmitters (such as dopamine and adrenaline) that convey the neuronal information of the central and vegetative nervous system. Amphetamine was first synthesized in 1887 but was not used for medical purposes until the early 1930s, when it was found to increase blood pressure, stimulate the central nervous system, to be effective against asthma and was useful in treating an epileptic seizure disorder. On the illicit drug market amphetamines have been sold as powders, liquids, crystals, tablets, and capsules.
The most common amphetamine derivatives on the illicit drug market include amphetamine sulfate, methylamphetamine, methylenedioxy amphetamine (MDA), methylenedioxy methyl amphetamine (MDMA), and methylenedioxy ethyl amphetamine (MDEA). Dosages in powders and tablets vary considerably but are generally in the range of 50–250 mg of drug in a single dose. Most, if not all, amphetamine and related compounds are synthesized in clandestine laboratories by various synthetic routes. As well as the drugs themselves being legislatively controlled, the synthetic precursors (e.g., benzyl methyl ketone (BMK), piperonyl methyl ketone (PMK), 1-phenyl- 2-propanone (P-2-P) and safrole), and pre-precursors (e.g., alphaphenylaceto-acetonitrile (APAAN) the precursor of BMK; phenylaceticacid, a precursor of P-2-P) are also controlled and closely monitored.
Ecstasy
When the term Ecstasy was first used in the early 1970s it was an American street name for preparations containing the active agent MDMA. Now the term describes tablets or capsules predominantly containing one or more (or combinations) of psychotropic active agents derived from the β-phenethylamine group.
Production and trafficking of amphetamine-type-stimulants (ATS)
There are well established global markets for amphetamine type stimulants (ATS) with distinct geographical variations. Amphetamine consumption and trafficking is more commonly observed in the Near and Middle East and Western and Central Europe. Methamphetamine synthesis and consumption in particular is increasing and there is high demand from East Asia, South East Asia, Oceania, and North America. Methamphetamine in the United States now primarily originates from large-scale clandestine laboratories in Mexico and the drug is then smuggled across the south western border of the United States. It is the second most commonly observed drug type in United States forensic laboratories after cannabis. Synthetic drugs, particularly amphetamine and ecstasy, are the second largest type of drug consumed in Europe. Unlike with other drugs of abuse the European Union is a major producer of these compounds, with Belgium, the Netherlands, Germany, and Poland being considered to be the main production sites. Illicit amphetamine and ecstasy laboratories have been found in 10 member states of the EU. Many laboratories are also known to exist in Eastern European countries such as Poland, Bulgaria, the Czech Republic, and the Baltic states. These laboratories can vary from simple kitchens to professional laboratories with consequent variability in production capacity but in Europe the majority of disrupted clandestine laboratories have been relatively small-scale operations. Such laboratories also produce large quantities of chemical waste with associated disposal problems.
Benzodiazepines
Benzodiazepines, therapeutically used as tranquilizers, hypnotics, anticonvulsants, and centrally acting muscle relaxants, rank among the most frequently prescribed drugs. In 1960, the first benzodiazepine, chlordiazepoxide, was introduced. To date, > 50 benzodiazepines have been marketed in over 100 different preparations. They appear mainly as capsules and tablets, however some are marketed in other forms such injectable solutions or powders. Benzodiazepines were introduced to replace barbiturates and methaqualone as tranquilizers, hypnotics, anticonvulsants and muscle relaxants. Currently there are 36 benzodiazepines on the United Nations Convention on Psychotropic Substances of 1971 control list including diazepam, alprazolam, and nitrazepam. A further 21 novel, or “designer” benzodiazepines have recently been detected on the illicit drug market, for example, etizolam and flubromazepam and are considered to be novel psychoactive substances. Many benzodiazepines, particularly in tablet form, available on the illicit drug market are diverted medicines as well as being illicitly manufactured, often visually similar to commercial tablets but containing a range of compounds which can change over time. In the United Kingdom, Etizolam, licensed only for use in India, Italy, and Japan and appearing in both diverted, but predominantly illicitly manufactured tablets has become one of the most commonly seized benzodiazepines, particularly in Scotland.
Synthetic Opioids
Synthetic opioids mimic the effects of naturally occurring or semisynthetic opiates. Such substances include buprenorphine, methadone, tramadol, pentacozine, pethidine, and fentanyl among others and are legitimately used as medicines and all are subject to nonmedical use. Fentanyl, a potent synthetic opioid, was first synthesized in 1959 and a number of related compounds were licensed following its introduction. These include carfentanil, a very potent fentanyl analogue designed for use with large animals and never licensed for human use. Medical fentanyl preparations include lozenges, tablets, injectable formulations, sprays, and transdermal patches. Nonmedical, illicitly produced fentanyl is becoming increasingly common, mixed with heroin, particularly in the North American markets with drug deaths from opioid overdoses increasing rapidly in recent years.
New/Novel Psychoactive Substances (NPS)
NPS are often former research chemicals and/or pharmaceutical drug candidates not taken forward to clinical trials; adaptations of such compounds; substances similar to existing controlled drugs whose molecular structure has been modified in order to optimize their effect and bypass national and international laws; or are completely new or novel substances. Over 700 new or novel substances have appeared on international illicit drug markets since 2005. The majority have relatively low prevalence compared to the more traditionally abused drugs, however some can be highly potent and have caused specific localized poisoning and intoxification events when a new, previously untested drug or drug product arrives on the market. NPS pose a particular challenge to analytical laboratories as they appear and disappear relatively quickly, there is often a lack of reference standards available to compare them to for the purpose of unequivocal identification and their toxicological and pharmacological profiles are often unknown or little researched and metabolites, which are often observed in biological fluids after the drug has been consumed, are unknown and their biological activity and effects are not understood. Such substances are reported to be produced in bulk in China (although there are other sources) and either transported in bulk for repackaging, processing, and sale by other vendors or are bought directly by users from vendors via clear- and dark-web sites on the internet.
The sheer number of new or novel substances entering the illicit drugs market since 2008 means that it is not possible to cover them in depth here. Such novel drugs can be classified either by chemical structure or their biological effects. The main classes are (i) the synthetic cannabinoid receptor agonists (SCRAs), potent drugs designed to mimic the effects of Δ9-THC by interacting, often more effectively, with the same pharmacological receptors which mediate the effects of Δ9-THC, for example, AMB-FUBINACA/FUB-AMB, 5F-ADB/5F-MDMB-PINACA, ADB-FUBINACA, MDMB-CHMICA, and AB-FUBINACA; (ii) the synthetic cathinones, for example, mephedrone, N-ethylpentylone, dibutylone, α-PVP (flakka); (iii) novel psychedelics/hallucinogens, tryptimines, and phenethylamines, for example, N,N-diallyltryptamine (DALT) derivatives such as N,N-di allyl-5-methoxy tryptamine (5-MeO-DALT), 1-propionyl-d-lysergic acid diethylamide, 2,5-dimethoxy-4-bromophenethylamine (2C–B) and 2,5-dimethoxy-4-iodophenethylamine (2C–I) and the NBOMe analogues such as 25I-NBOMe 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethan-amine); (iv) novel synthetic opioids, for example, furanyl fentanyl, U-47700 and its analogues, and MT-45 and (v) piperazines, for example, benzylpiperazine (BZP) and 3-trifluoromethyl-phenylpiperazine (TFMPP).Read more
Pharmaceutical applications of 1,4-benzodiazepines
Zahra Nikfarjam, … Ronald W. Brown, in Benzodiazepine-Based Drug Discovery, 2022
5.4.4 Flurazepam
Introduction: Flurazepam (as a generic name) under the brand name of Dalmane or Dalmadorm and IUPAC name of 7-chloro-1-(2-(diethylamino)ethyl)-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one is a long-acting 1,4-benzodiazepine known as a hypnotic drug for the treatment of insomniacs with difficulty in falling asleep, frequent nocturnal awakenings, and early morning awakenings (The US Food and Drug, 2007). It was initially introduced to the US as a sleep-inducing agent in 1970 and soon later became popular reaching 6.5 million prescriptions in 1973. Flurazepam is available as a yellow crystalline dihydrochloride salt that is highly soluble in water and alcohol. This medication is more potent than a placebo and displays the same efficiency as other hypnotic drugs in short-term treatments. However, flurazepam is more effective in long-term dosage therapy than other hypnotics such as barbiturates, glutethimide, chloral hydrate, meprobamate, and methaqualone (Greenblatt et al., 1975a). These medications become ineffective when administrated constantly over two weeks, however, flurazepam persists to provide pharmacologically effects even when ingested repeatedly for up to 4 weeks (Kales et al., 1970). These features signify flurazepam’s advantages over other nonbenzodiazepine hypnotics.
Pharmacodynamics: Several studies have described that flurazepam displays more central CNS depression and less anxiety reduction than other benzodiazepines (Randall et al., 1969; Tseng & Wang, 1971), which clarifies flurazepam’s usage as a hypnotic rather than as an antianxiety drug. These observations demonstrate that flurazepam acts as a central muscle relaxant via blockade of GABAergic interneurons at supraspinal level with no effects on the spinal cord. Cannizzaro and co-workers investigated the effect of flurazepam on rats after single-dose administration, where the medication resulted in CNS depression but no behavioral disinhibition (Cannizzaro et al., 1972). However, the mice showed tolerance to the depressant effects of flurazepam upon repeated ingestion, followed by the appearance of behavioral disinhibition. The drug has also an inhibitory effect on the direct electrical stimulation of interneurons in the brainstem reticular system, exhibiting no impact on both monosynaptic and polysynaptic reflex behaviors (Greenblatt et al., 1975a). In a study on mice given ataxia-producing doses of several benzodiazepines (Fennessy & Lee, 1972), it was shown that flurazepam decreases the amount of dopamine in their brain, whereas other benzodiazepines including diazepam, nitrazepam, chlordiazepoxide, clonazepam, and medazepam represent either no change or increased the dopamine brain content. Although many studies have been carried out on flurazepam behavior, the clinical connection of these analyses is not known yet.
Metabolism: Flurazepam concentration in the blood after administration is extremely low, which is observable only for a few hours after a single dose (Miller et al., 1988). The metabolic pathway of flurazepam is represented in Fig. 5.9, consisting of the formation of three metabolites. Flurazepam is quickly absorbed from the GI tract (within 30 min) and biotransformed to its metabolic derivatives. Concentrations of two major metabolites, e.g., hydroxyethyl flurazepam and desalkylflurazepam, become significantly high after approximately one hour of administration, where the desalkylflurazepam metabolite stays in the blood for a longer period. Therefore, these pharmacologically active metabolites may cause flurazepam’s clinical effects in the human body (Miller et al., 1988). Flurazepam and its metabolic derivatives are finally excreted in the urine, where hydroxyethyl flurazepam and desalkylflurazepam consist of 22%–55% and 1% of the dose, respectively.
Pharmacokinetics and dosage: In a clinical study, Greenblatt et al. have made an analysis on the pharmacokinetics of desalkylflurazepam as the major metabolite in 26 healthy noninsomniac volunteers aging from 19 to 85 years old after orally given 15 mg single dose of flurazepam (Greenblatt et al., 1981). Maximum desalkylflurazepam plasma concentration ranging from 5.0 to 20.2 ng/mL occurs between 0.5 and 96 h after administration, which is found to be higher in females possibly due to their lower body weights (Table 5.19). The elimination half-life of the metabolite increases with age in both genders as changes in body composition with age may influence the drug uptake of tissues, leading to altered pharmacokinetics. In a similar clinical analysis, the relative contribution of the parent drug and its metabolites in the human blood was investigated (Table 5.20) (Miller et al., 1988). The mean maximum plasma levels of flurazepam and flurazepam aldehydes are 2.4 and 7.8 ng/mL, respectively, which become undetectable within the respective 3 h and 6.9 h after administration. Hydroxyethyl flurazepam reaches the average concentration level of 15 ng/mL after 1.1 h, becoming unobservable after 8 h. On the contrary, desalkylflurazepam shows the highest plasma peak concentration (20.4 ng/mL) that occurs at 10.2 h after dosing with an average t1/2 = 71.4 h. This metabolite remains in the blood much longer than other species, which is still detectable after 9 days of administration.
Table 5.19. Pharmacokinetic parameters of desalkylflurazepam as the major flurazepam metabolite after single 15 mg oral dose.
| Gender (age) | Weight (kg) | Cmax (ng/mL) | Tmax (h) | t1/2 (h) |
|---|---|---|---|---|
| Male (19–34) | 62–86 | 5.3–9.6 | 0.5–16 | 37–118 |
| Female (20–33) | 52–61 | 11.5–20.0 | 0.75–73 | 35–133 |
| Male (66–72) | 66–89 | 8.2–15.1 | 0.75–96 | 71–289 |
| Female (61–85) | 46–73 | 10.3–19.1 | 0.75–24 | 85–165 |
Table 5.20. Pharmacokinetic parameters of flurazepam and its metabolites after single 30 mg oral dose.
| Species | Cmax (mean) (ng/mL) | Tmax (mean) (h) | Total AUC (mean) (ng/ml × h) | t1/2 (mean) (h) |
|---|---|---|---|---|
| Flurazepam | 0–10 (2.4) | 0.5–2.0 (1.0) | 0.5–4.4 (1.8) | 0–19.0 (5.3) |
| Flurazepam aldehyde | 3.1–19.3 (7.8) | 0.75–2.5 (1.3) | 1.3–28.9 (6.9) | 7.4–155.7 (48.3) |
| Hydroxyethyl flurazepam | 7.1–23.4 (15.1) | 0.75–2.0 (1.1) | 0.9–2.4 (1.3) | 14.8–65.2 (38.4) |
| Desalkylflurazepam | 7.4–47.0 (20.4) | 1.0–72 (10.2) | 34.1–154 (71.4) | 911–3084 (1969) |
Flurazepam is marketed as capsules containing 15 mg or 30 mg flurazepam hydrochloride (The US Food and Drug, 2007). The recommended dosage for adults is 30 mg before sleeping at night. However, this drug amount is reduced to 15 mg for elderly people (> 65 years old). There have been no clinical analysis of flurazepam in children, which is why this medication is not recommended for use in people under 15 years old.
Adverse effects: Flurazepam has an advantage over other hypnotics as there is no rapid eye movement (REM) rebound observed upon discontinuation of the drug (Isjanovski & Isjanovski, 2019). According to the FDA flurazepam instruction label, hangover, drowsiness, headache, and dry mouth are the most common side effects of flurazepam (The US Food and Drug, 2007). Studies have also shown that this drug has significantly less potential for abuse and displays less toxicity when ingested in excess (Greenblatt et al., 1975a; Greenblatt et al., 1975b). Flurazepam decreases the sleep time in stages 3 and 4, being maintained drug the medication withdrawal (Kales et al., 1971). Flurazepam is categorized as a Class X by the FDA, indicating that it should not be used during pregnancy (The US Food and Drug, 2007). Despite the global extensive administration of flurazepam, there is little clinical information available about its effect on the fetus during pregnancy. A study on the effect of flurazepam during organogenesis of the rat fetus has described that the medication ingestion during the second half of pregnancy may result in severe physical abnormalities (Takzare et al., 2008). The FDA has also reported the presence of high plasma concentration of desalkylflurazepam in the infant due to the transplacental transfer of this long-acting metabolite to the fetal circulation (The US Food and Drug, 2007).
Interactions: Common nonbenzodiazepine hypnotics such as barbiturates and glutethimide are known to modulate the performance of hepatic microsomal enzymes, causing severe interactions with other drugs, especially in the case of oral anticoagulant drugs. In contrast, flurazepam exhibits no significant enzyme induction, where it can be prescribed to patients simultaneously taking oral anticoagulants (Greenblatt et al., 1975b). Several studies have also shown that there is no noticeable interaction of small doses of flurazepam with alcohol in the human (Greenblatt et al., 1975b). Nevertheless, patients should be advised that flurazepam in high dosages may increase the CNS depression resulted from alcohol and other CNS-depressant drugs.Read more
Tandem mass spectrometry of organic nitro and halogen compounds: Competition between losses of molecules and of radicals
W.M.A. Niessen, in International Journal of Mass Spectrometry, 2021
3.5.1 Nitrazepam and related compounds
The nitro-group containing benzodiazepines nitrazepam ([M+H]+ with m/z 282.0873; [C15H12N3O3]+), flunitrazepam ([M+H]+ with m/z 314.0935; [C16N13FN3O3]+), and clonazepam ([M+H]+ with m/z 316.0483; [C15H11ClN3O3]+) show an abundant product ion due to the primary loss of the nitryl radical (•NO2), eventually in competition with a low-abundant product ion consistent with the loss of carbon monoxide (CO). At higher collision energy, the loss of •NO2 is in competition with the loss of dioxo-λ5-azane (HNO2), as is also frequently observed with the loss of other radicals, such chlorine (•Cl) and bromine (•Br) radicals (Section 4). At higher collision energy, additional fragmentation is observed, partly as secondary fragmentation of the odd-electron product ion, resulting from the initial loss of •NO2. In this, their fragmentation differs from that of other benzodiazepines, where the loss of CO is the primary fragmentation route [20].
In negative-ion mode, nitrazepam ([M–H]– with m/z 280.0728; [C15H10N3O3]–) shows product ions with m/z 252 due to the loss of CO, with m/z 222 due to the subsequent loss of a nitrosyl radical (•NO) or with m/z 206 due to the subsequent loss of •NO2, and m/z 194 due to the loss of CO from the ion with m/z 222.
Analysis of certain tranquilizers in biological fluids
M.M Hefnawy, in Journal of Pharmaceutical and Biomedical Analysis, 2002
A difference spectrophotometric method was reported for the determination of clonazepam and nitrazepam in biological fluids [117]. The use of fifth-order derivative spectrophotometry enabled the direct determination of nitrazepam in urine at 388 nm with a limit of detection of 1 μg/ml, but in plasma was carried out directly by fourth-order derivative spectrometry at 402 nm with a limit of detection of 1.5 μg/ml. Clonazepam was determined directly in urine by sixth-order derivative spectrometry at 384 nm with a limit of detection 1 μg/ml and in plasma by fourth-order derivative spectrometry at 384 nm with a limit of detection at 0.5 ppm. Similarly, chlordiazepoxide, diazepam, nordiazepam and oxazepam were determined in urine sample containing all these compounds by zero, first and second order derivative with spectra between 300 and 500 nm. The recoveries were 92–97% [118]. Also, Randez-Gil et al. [119] reported a third-order derivative UV spectrum of clonazepam in urine with detection limit of 150 ppb. An automatic kinetics spectrophotometry determination of oxazepam in urine was reported by continuous addition of NaNO2 and α-naphthol to oxazepam after hydrolysis with 6 M HCl and measured the colored at 530 nm [120].
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Toxicology covers a wide range of disciplines, including therapeutic drug monitoring, clinical toxicology, forensic toxicology (drug driving, criminal and …
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NitrazolaM, with the chemical formula C6H6N4O2, has the CAS number 28910-99-8. It appears as a white to off-white crystalline powder with no distinct odor.
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