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Substance Name: Methaqualone [USAN:USP:INN:BAN]
RN: 72-44-6
UNII: 7ZKH8MQW6T
InChIKey: JEYCTXHKTXCGPB-UHFFFAOYSA-N

Note

  • A quinazoline derivative with hypnotic and sedative properties. It has been withdrawn from the market in many countries because of problems with abuse. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604)

Molecular Formula

  • C16-H14-N2-O

Molecular Weight

  • 250.2996
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Hypnotics and Sedatives
  • Reproductive Effect
  • Sedative-Hypnotic

Superlist Classification Code

  • DEA Schedule I
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Names and Synonyms

Name of Substance

  • Methaqualone
  • Methaqualone [USAN:USP:INN:BAN]

MeSH Heading

  • Methaqualone

Synonyms

  • 2-Methyl-3-(2-methylphenyl)-4(3H)-quinazolinone
  • 2-Methyl-3-(2-methylphenyl)-4-quinazolinone
  • 2-Methyl-3-(2-tolyl)quinazol-4-one
  • 2-Methyl-3-(o-tolyl)-3,4-dihydro-4-quinazolinone
  • 2-Methyl-3-o-tolyl-4(3H)-chinazolinon
  • 2-Methyl-3-o-tolyl-4(3H)-chinazolinon [German]
  • 2-Methyl-3-o-tolyl-4(3H)-chinazolone
  • 2-Methyl-3-o-tolyl-4(3H)-quinazolinone
  • 2-Methyl-3-o-tolyl-4-quinazolone
  • 2-Methyl-3-tolyl-4-oxybensdiazine
  • 3,4-Dihydro-2-methyl-4-oxo-3-o-tolylquinazoline
  • 5-24-03-00132 (Beilstein Handbook Reference)
  • Aqual
  • BRN 0211874
  • Cateudyl
  • CI-705
  • Citexal
  • CN 38703
  • Dormigoa
  • Dormigoa-Schlafmittel
  • Dormogen
  • Dormutil
  • Dorsedin
  • EINECS 200-780-4
  • Fadormir
  • Holodorm
  • HSDB 3120
  • Hyminal
  • Hypocol
  • Hyptor
  • Hyptor Base
  • Ipnofil
  • MAOA
  • Melsed
  • Melsedin Base
  • Melsomin
  • Mequin
  • Metachalon
  • Metachalon [Czech]
  • Metacualona
  • Metacualona [INN-Spanish]
  • Metakvalon
  • Metaqualon
  • Metaqualone
  • Metaqualone [DCIT]
  • Methachalonum
  • Methaqualon
  • Methaqualone
  • Methaqualoneinone
  • Methaqualonum
  • Methaqualonum [INN-Latin]
  • Methased
  • Methyl-o-tolylquinazolone
  • Metolquizolone
  • Mollinox
  • Motolon
  • Mozambin
  • MTQ
  • Nobedorm
  • Noctilene
  • Normi-nox
  • NSC 111388
  • Omnyl
  • Optinoxan
  • Orthonal
  • Ortonal
  • Parminal
  • Pro-Dorm
  • Quaalude
  • QZ 2
  • QZ-2
  • R-148
  • Revonal
  • RIC 272
  • Rorer 148
  • Rorer 714
  • Roulone
  • Rouqualone
  • Sindesvel
  • Somberol
  • Somnafac
  • Somnomed
  • Sonal
  • Sopor
  • Soverin
  • Torinal
  • TR-495
  • Tuazole
  • Tuazolone
  • UNII-7ZKH8MQW6T

Systematic Names

  • 4(3H)-Quinazolinone, 2-methyl-3-(2-methylphenyl)-
  • 4(3H)-Quinazolinone, 2-methyl-3-o-tolyl-
  • Methaqualone

Superlist Names

  • DEA No. 2565
  • Methaqualone

Registry Numbers

CAS Registry Number

  • 72-44-6

FDA UNII

  • 7ZKH8MQW6T

Other Registry Number

  • 93240-42-7

System Generated Number

  • 0000072446

Structure Descriptors

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

Smiles

Cc1ccccc1n2c(nc3ccccc3c2=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intraperitoneal 235mg/kg (235mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Farmakologiya i Toksikologiya Vol. 27, Pg. 413, 1964.
human TDLo oral 57mg/kg (57mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archiv fuer Toxikologie. Vol. 20, Pg. 31, 1963.
man LDLo oral 114mg/kg (114mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Archiv fuer Toxikologie. Vol. 20, Pg. 31, 1963.
mouse LD50 intraperitoneal 180mg/kg (180mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: STIFFNESS
Indian Journal of Medical Research. Vol. 69, Pg. 1008, 1979.
mouse LD50 oral 420mg/kg (420mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 42, 1959.
mouse LD50 parenteral 500mg/kg (500mg/kg) BEHAVIORAL: ANALGESIA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: TREMOR
Pharmaceutical Chemistry Journal Vol. 7, Pg. 626, 1973.
rabbit LD50 intravenous 100mg/kg (100mg/kg)   Archiv fuer Toxikologie. Vol. 20, Pg. 31, 1963.
rat LD50 intraperitoneal 125mg/kg (125mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 242, 1967.
rat LD50 oral 185mg/kg (185mg/kg)   Journal of Medicinal Chemistry. Vol. 24, Pg. 490, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 120 deg C   EXP
log P (octanol-water) 4.330 (none)   EST
Water Solubility 4.730 mg/L 25 EST
Vapor Pressure 1.16E-07 mm Hg 25 EST
Henry's Law Constant 2.76E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.66E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.