2-methyl-3-(2-methylphenyl)-3,4-dihydroquinazolin-4-one

• ChemBase ID: 4377
• Molecular Formular: C16H14N2O
• Molecular Mass: 250.29516
• Monoisotopic Mass: 250.11061308
• SMILES: O=c1n(c2c(cccc2)C)c(nc2c1cccc2)C
• Canonical SMILES: Cc1nc2ccccc2c(=O)n1c1ccccc1C
• InChI: InChI=1S/C16H14N2O/c1-11-7-3-6-10-15(11)18-12(2)17-14-9-5-4-8-13(14)16(18)19/h3-10H,1-2H3
• InChIKey: JEYCTXHKTXCGPB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-3-(2-methylphenyl)-3,4-dihydroquinazolin-4-one
• IUPAC Traditional name: methaqualone; sonal
• Brand Name: Aqual; Cateudyl; Citexal; Dormigoa; Dormigoa-schlafmittel; Dormogen; Dormutil; Dorsedin; Fadormir; Holodorm; Hyminal; Hyminal monohydrochloride; Hypcol; Hypocol; Hyptor; Hyptor base; Ipnofil; Melsed; Melsed HCL; Melsedin; Melsomin; Mequal; Mequin; Metakvalon; Metaqualon; Methachalonum; Methaqualon; Methaqualoneinone; Methased; Metolquizolone; Mollinox; Motolon; Mozambin; Nethaqualone; Nobedorm; Noctilene; Normi-nox; Omnyl; Optimil; Optinoxan; Orthonal; Ortonal; Parest; Parminal; Pro-dorm; QZ 2 hydrochloride; Quaalude; Quaalude hydrochloride; Revonal; Rorer 148; Rorer 714; Roulone; Rouqualone; Sindesvel; Somberol; Somnafac; Somnofac; Somnomed; Sonal; Sopor; Sopor hydrochloride; Soverin; TR 495 monohydrochloride; Torinal; Tuazol; Tuazole; Tuazolone
• Synonyms: 2-Methyl-3-(2-methyl-phenyl)-4(3H)-quinazolinone; Sopor; Lude; Quaalude; Mandrax; Metolquizolone; QZ-2; Parest; Somnafac; NSC 111388; NSC 126877; NSC 631628; Methaqualone solution; 2-Methyl-3-o-tolyl-4(3H)-chinazolinon [German]; 2-Methyl-3-o-tolyl-4 (3H)-chinazolinon; 2-Methyl-3-o-tolyl-3H-quinazolin-4-one; 2-Methyl-3-(o-tolyl)-4-quinazolone hydrochloride; 2-Methyl-3-(o-tolyl)-4(3H)-quinazolinone hydrochloride; 2-Methyl-3-(o-tolyl)-3,4-dihydro-4-quinazolinone; 2-Methyl-3-(2-tolyl)quinazol-4-one; 2-Methyl-3-(2-methylphenyl)-4-quinazolinone; 2-Methyl-3-(2-methylphenyl)-4(3H)-quinazolinone; 3,4-Dihydro-2-methyl-4-oxo-3-o-tolylquinazoline; 2-Methyl-3-tolylchinazolon-4 hydrochloride; 2-Methyl-3-tolyl-4-oxybensdiazine; 2-Methyl-3-o-tolyl-4-quinazolone; 2-Methyl-3-o-tolyl-4(3H)-quinazolinone; 2-Methyl-3-o-tolyl-4(3H)-chinazolone; Diamthazole dihydrochloride; MAOA; Metachalon [czech]; Metacualona [inn-spanish]; Metaqualone [dcit]; Methaqualone hydrochloride; Methaqualonum [inn-latin]; Methyl-o-tolylquinazolone; Methylquinazolone hydrochloride; MTQ; MTQ hydrochloride; Methaqualone; 安眠酮 溶液

Database IDs

• CAS Number: 72-44-6
• MDL Number: MFCD00057320
• PubChem SID: 160967809; 46507178
• PubChem CID: 6292
• ATC CODE: N05CM01
• CHEMBL: 282052
• Chemspider ID: 6055
• DrugBank ID: DB04833
• KEGG ID: D00557
• Unique Ingredient Identifier: 7ZKH8MQW6T
• Wikipedia Title: Methaqualone

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.1684964
• LogD (pH = 7.4): 3.1684964
• Log P: 3.1684964
• Molar Refractivity: 77.1054 cm^3
• Polarizability: 28.366055 Å^3
• Polar Surface Area: 32.67 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.54
• LOG S: -3.79
• Solubility (Water): 4.07e-02 g/l

PROPERTIES

Physical Property

• Melting Point: 113°C (235.4°F)

Safety Information

• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1992
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• RID/ADR: UN 1992 3/PG 2
• Drug Control: kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Legal Status: Schedule I (US); Schedule III (Canada)
• Pregnancy Category: D (US)

Product Information

• Concentration: 1 mg/mL in methanol
• Grade: drug standard
• Empirical Formula (Hill Notation): C16H14N2O

DETAILS

DrugBank - DB04833

• Drug Groups: illicit; withdrawn
• Description: Methaqualone is a sedative-hypnotic drug that is similar in effect to barbiturates, a general central nervous system depressant. The sedative-hypnotic activity was first noted by Indian researchers in the 1950s and in 1962 methaqualone itself was patented in the US by Wallace and Tiernan. Its use peaked in the early 1970s as a hypnotic, for the treatment of insomnia, and as a sedative and muscle relaxant. It has also been used illegally as a recreational drug, commonly known as Quaaludes, Sopors, Ludes or Mandrax (particularly in the 1970s in North America) depending on the manufacturer. Since at least 2001, it has been widely used in South Africa, where it is commonly referred to as "smarties" or "geluk-tablette" (meaning happy tablets). Clandestinely produced methaqualone is still seized by government agencies and police forces around the world. [Wikipedia]
• Indication: For the treatment of insomnia, and as a sedative and muscle relaxant.
• Toxicity: Symptoms of overdose include delirium, convulsions, muscle spasms or seizure, cardiac arrest, shortness or loss of breath, vomiting or nausea, and coma or death. The LD50 for mice is 1250 mg/kg and for rats is 326 mg/kg (Strasenburg Labs).
• Affected Organisms: Humans and other mammals
• References: Potential Analgesics. Part I. Synthesis of substituted 4-quinazolones, I. K. Kacker and S. H. Zaheer, J. Ind. Chem. Soc. 28 (1951), pp. 344–346.
• External Links: Wikipedia

Toronto Research Chemicals - M225900

A quinazoline sedative-hypnotic. Controlled substance.

REFERENCES

• Potential Analgesics. Part I. Synthesis of substituted 4-quinazolones, I. K. Kacker and S. H. Zaheer, J. Ind. Chem. Soc. 28 (1951), pp. 344–346.
• Brown, S.S., et al.: Clin. Pharmacol. Ther., 14, 314 (1973)
• Patel, M., et al.: Anal. Profiles Drug Subs., 4, 245 (1973)