Nitromethaqualone

Nitromethaqualone
Nitromethaqualone
Systematic (IUPAC) name
2-methyl-3-(2-methoxy-4-nitrophenyl)-4(3H)-quinazolinone
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 340-52-3
ATC code None
PubChem CID 63339
ChemSpider 57006
Chemical data
Formula C16H13N3O4 
Mol. mass 311.29
SMILES eMolecules & PubChem

Nitromethaqualone (Parnox)[1] is an analogue of methaqualone which has similar sedative and hypnotic properties.[2] It is significantly more potent (10x) compared to the parent compound; the typical dose is approximately 25 mg.[3] However the aromatic nitro group is metabolised to the corresponding aniline which proved to be a mutagen,[4][5] and consequently nitromethaqualone was not developed further due to toxicity concerns.

References

  1. ^ Patent US 3162634 
  2. ^ Szirmai, A. (1963). "Pharmacological and Therapeutic Studies with a New Quinazolone Derivative, Nitromethaqualone". Therapeutische Umschau. Revue therapeutique 20: 542–546. PMID 14101319.  edit
  3. ^ Van Boven, M.; Daenens, P. (1982). "Biotransformation and excretion of nitromethaqualone in rats and humans". Journal of pharmaceutical sciences 71 (10): 1152–1157. doi:10.1002/jps.2600711019. PMID 7143214.  edit
  4. ^ J Pharm Sci 1982, 71(10), p.1152
  5. ^ Annales des Falsifications de l'Expertise Chimique et Toxicologique 1987, 80(854), p.25
v · d · eHypnotics/Sedatives (N05C)
GABAA Agonists/PAMs
Barbiturates: Allobarbital • Amobarbital • Aprobarbital • Barbital • Butabarbital • Butobarbital • Cyclobarbital • Ethallobarbital • Heptabarbital • Hexobarbital • Mephobarbital • Methohexital • Pentobarbital • Phenobarbital • Proxibarbal • Reposal • Secobarbital • Talbutal • Thiamylal • Thiopental • Vinbarbital • Vinylbital; Benzodiazepines: Brotizolam • Clonazepam • Cinolazepam • Climazolam • Doxefazepam • Estazolam • Flunitrazepam • Flurazepam • Flutoprazepam • Haloxazolam • Loprazolam • Lormetazepam • Midazolam • Nimetazepam • Nitrazepam • Quazepam • Temazepam • Triazolam; Carbamates: Carisoprodol • Ethinamate • Hexapropymate • Meprobamate • Methocarbamol • Procymate • Tybamate; Neuroactive Steroids: Acebrochol • Allopregnanolone • Alphadolone • Alphaxolone • Eltanolone • Ganaxolone • Hydroxydione • Minaxolone • Org 20599 • Org 21465 • Tetrahydrodeoxycorticosterone; Nonbenzodiazepines: CL-218,872 • Eszopiclone • Indiplon • JM-1232 • Lirequinil • Necopidem • Pazinaclone • ROD-188 • Saripidem • Suproclone • Suriclone • SX-3228 • U-89843A • U-90042 • Zaleplon • Zolpidem • Zopiclone; Phenols: Fospropofol • Propofol; Piperidinediones: Glutethimide • Methyprylon • Pyrithyldione • Piperidione; Quinazolinones: Afloqualone • Cloroqualone • Diproqualone • Etaqualone • Mebroqualone • Mecloqualone • Methaqualone • Methylmethaqualone • Nitromethaqualone; Others: 2-Methyl-2-butanol • Acetophenone • Acetylglycinamide chloral hydrate • Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Centalun • Chloral hydrate • Chloralose • Chloralodol • Clomethiazole • Dichloralphenazone • Ethanol (Alcohol) • Ethchlorvynol • Etomidate • Gaboxadol • Loreclezole • Methylpentynol • Metomidate • Paraldehyde • Petrichloral • Sulfonmethane • Trichloroethanol • Triclofos • Valerenic acid (Valerian)
GABAB Agonists
1,4-Butanediol • Aceburic acid • GABOB • GHB • GBL • GVL
H1 Inverse agonists
α1-Adrenergic Antagonists
α2-Adrenergic Agonists
5-HT2A Antagonists
Melatonin Agonists
Agomelatine • LY-156,735 • Melatonin • Ramelteon • Tasimelteon
Orexin Antagonists
Almorexant • SB-334,867 • SB-408,124 • SB-649,868 • Suvorexant • TCS-OX2-29
Others


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