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Chemistry

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Also known as: Metolquizolone, 72-44-6, Quaalude, Methaqualoneinone, Metaqualon, Methaqualon
Molecular Formula
C16H14N2O
Molecular Weight
250.29  g/mol
InChI Key
JEYCTXHKTXCGPB-UHFFFAOYSA-N
FDA UNII
7ZKH8MQW6T

Metaqualone
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 It has been withdrawn from the market in many countries because of problems with abuse.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)
1 2D Structure

Metaqualone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methyl-3-(2-methylphenyl)quinazolin-4-one
2.1.2 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
2.1.3 InChI Key
JEYCTXHKTXCGPB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC=CC=C1N2C(=NC3=CC=CC=C3C2=O)C
2.2 Other Identifiers
2.2.1 UNII
7ZKH8MQW6T
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Hydrochloride, Methaqualone

2. Methaqualone Hydrochloride

3. Metolquizolone

4. Optimil

5. Ortonal

6. Quaalude

2.3.2 Depositor-Supplied Synonyms

1. Metolquizolone

2. 72-44-6

3. Quaalude

4. Methaqualoneinone

5. Metaqualon

6. Methaqualon

7. Ortonal

8. Cateudyl

9. Melsomin

10. Metakvalon

11. Tuazolone

12. Tuazole

13. Aqual

14. Dormigoa

15. Dormogen

16. Dormutil

17. Dorsedin

18. Fadormir

19. Holodorm

20. Methased

21. Mollinox

22. Mozambin

23. Nobedorm

24. Noctilene

25. Optinoxan

26. Orthonal

27. Parminal

28. Rouqualone

29. Sindesvel

30. Somberol

31. Somnomed

32. Hyminal

33. Hypocol

34. Hyptor

35. Ipnofil

36. Melsed

37. Motolon

38. Revonal

39. Roulone

40. Soverin

41. Torinal

42. Omnyl

43. Sonal

44. Sopor

45. Hyptor Base

46. Normi-nox

47. Citexal

48. Mequin

49. 3,4-dihydro-2-methyl-4-oxo-3-o-tolylquinazoline

50. Melsedin Base

51. Dormigoa-schlafmittel

52. Maoa

53. Pro-dorm

54. Rorer 148

55. Rorer 714

56. Somnafac

57. 2-methyl-3-(2-methylphenyl)-4(3h)-quinazolinone

58. Nethaqualone

59. Metachalon

60. 4(3h)-quinazolinone, 2-methyl-3-(2-methylphenyl)-

61. 2-methyl-3-o-tolyl-4-quinazolone

62. 2-methyl-3-tolyl-4-oxybensdiazine

63. Cn 38703

64. 2-methyl-3-o-tolyl-4(3h)-quinazolinone

65. Ci-705

66. Tr-495

67. Qz 2

68. R-148

69. 2-methyl-3-(2-tolyl)quinazol-4-one

70. Ric 272

71. 2-methyl-3-o-tolyl-4(3h)-chinazolone

72. Qz-2

73. 2-methyl-3-(2-methylphenyl)-4-quinazolinone

74. 2-methyl-3-(o-tolyl)-3,4-dihydro-4-quinazolinone

75. 2-methyl-3-o-tolyl-4(3h)-chinazolinon

76. 4(3h)-quinazolinone, 2-methyl-3-o-tolyl-

77. 7zkh8mqw6t

78. Mtq

79. Nsc-111388

80. Nsc-126877

81. Nsc-631628

82. Chebi:6821

83. 2-methyl-3-(2-methylphenyl)quinazolin-4-one

84. 2-methyl-3-(2-methylphenyl)quinazolin-4(3h)-one

85. Ci 705

86. Nsc631628

87. Tr 495

88. 2-methyl-3-(o-tolyl)quinazolin-4-one

89. Metachalon [czech]

90. Ncgc00245236-02

91. Cn-38703

92. Dsstox_cid_3279

93. Dsstox_rid_76954

94. Dsstox_gsid_23279

95. Metacualona [inn-spanish]

96. Methaqualonum [inn-latin]

97. Hypcol

98. Tuazol

99. Cas-72-44-6

100. Wln: T66 Bvn Enj Cr B1& D1

101. Hsdb 3120

102. Einecs 200-780-4

103. Unii-7zkh8mqw6t

104. Nsc 111388

105. 2-methyl-3-o-tolyl-4(3h)-chinazolinon [german]

106. Brn 0211874

107. Reposil

108. Dea No. 2565

109. Methaqualone [usan:usp:inn:ban]

110. Methaqualone [mi]

111. 2-methyl-3-(o-tolyl)quinazolin-4(3h)-one

112. (.+/-.)-methaqualone

113. Methaqualone [inn]

114. Methaqualone [jan]

115. Methaqualone [hsdb]

116. Methaqualone [usan]

117. Methaqualone [vandf]

118. Schembl43892

119. Methaqualone [mart.]

120. 5-24-03-00132 (beilstein Handbook Reference)

121. Mls000678342

122. Methaqualone [who-dd]

123. Chembl282052

124. Dtxsid7023279

125. 4(3h)-quinazolinone, 2-methyl-3-(2-methylphenyl)-, (-)-

126. Hms2626l18

127. Methaqualone [ep Impurity]

128. Zinc2568176

129. Methaqualone 0.1 Mg/ml In Methanol

130. Methaqualone 1.0 Mg/ml In Methanol

131. Tox21_112502

132. Tox21_112869

133. 2-methyl-3-o-tolylquinazolin-4-one

134. Nsc111388

135. Nsc126877

136. Stl386501

137. Akos000509786

138. Db04833

139. Nsc-111388-

140. Ncgc00245236-01

141. Smr000285241

142. 2-methyl-3-(o-tolyl)-3h-quinazolin-4-one

143. 4(3h)-quinazolinone, 2-methyl-3-o--tolyl-

144. C07560

145. D00557

146. 2-methyl-3-(o-tolyl)-quinazoline-4 (3h)-one

147. Q423912

148. J-511183

149. (2-methyl-3-(o-tolyl)-3,4-dihydro-4-(quinazolinone)

150. Methaqualone Solution, 1 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 250.29 g/mol
Molecular Formula C16H14N2O
XLogP32.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass250.110613074 g/mol
Monoisotopic Mass250.110613074 g/mol
Topological Polar Surface Area32.7 Ų
Heavy Atom Count19
Formal Charge0
Complexity390
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Sedatives, Nonbarbiturate

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


METHAQUALONE IS EFFECTIVE SEDATIVE & HYPNOTIC AGENT BUT LIKE SIMILAR DRUGS, MAY LOSE ITS EFFECTIVENESS BY 2ND WK OF CONTINUAL ADMIN. ... THIS DRUG IS PROBABLY SAFE FOR USE IN PATIENTS WITH HEREDITARY PORPHYRIA. /SRP: FORMER USE/

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 159


Mildly toxic doses ... are similar to those of other sedative-hypnotics. Coma lasting 4 and 90 hours after ingestion of 3 and 7.5 g, respectively, occurred.

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 597


MEDICATION: SEDATIVE-HYPNOTIC AGENT /SRP: FORMER USE/

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 159


A sedative hypnotic, anticonvulsant, antitussive, and weak antihistamine. It may potentiate analgesic properties of opioids (e.g., codeine). /SRP: former use/

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 727


4.2 Drug Warning

COMA HAS OCCURRED AFTER 2.4 G & DEATH AFTER 8 G. ... MOST FATALITIES OCCUR IN PERSONS WHO HAVE ALSO INGESTED ETHANOL. ... ABUSERS EMPLOY DOSES OF 75 MG-2 G/DAY, WITH AVG OF ABOUT 725 MG. SEVERE GRAND MAL CONVULSIONS MAY OCCUR AFTER ABRUPT WITHDRAWAL FROM HIGH DOSES ...

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 367


... PATIENTS ON THE DRUG SHOULD BE WARNED AGAINST DRIVING CAR OR OPERATING HAZARDOUS MACHINERY. ... USED WITH CAUTION IN PATIENTS WITH DEPRESSION OR SUICIDAL TENDENCIES & THOSE WITH LIVER DYSFUNCTION.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1018


... CONTRAINDICATED IN WOMEN WHO ARE OR MAY BECOME PREGNANT; ITS SAFE USE IN CHILDREN HAS NOT BEEN ESTABLISHED. PSYCHOLOGICAL DEPENDENCE HAS OCCURRED ... PHYSICAL DEPENDENCE HAS NOW REACHED ALARMING PROPORTIONS & SOME AUTHORITIES BELIEVE THAT POTENTIAL FOR ... ADDICTION & ABUSE ARE AS SERIOUS AS THOSE OF BARBITURATES & HEROIN.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1018


... SHOULD NOT BE USED FOR PERIODS LONGER THAN 3 MO. FURTHERMORE IT SHOULD NOT BE PRESCRIBED FOR ADDICTION-PRONE PATIENTS.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1018


4.3 Minimum/Potential Fatal Human Dose

Reputed oral ingestions in adults of 8 to 20 g (100-200 mg/kg) have caused death. An adult who ingested 24 g (300 mg/kg) survived with supportive care.

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 597


4.4 Drug Indication

For the treatment of insomnia, and as a sedative and muscle relaxant.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Hypnotics and Sedatives

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)


5.2 ATC Code

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CM - Other hypnotics and sedatives

N05CM01 - Methaqualone


5.3 Absorption, Distribution and Excretion

IN MAN, 99% OF METHAQUALONE IS ABSORBED IN 2 HOURS. IN THE PLASMA, 70 TO 90% IS BOUND TO ALBUMIN. ... METABOLITES ... ARE MAINLY CONJUGATED AND EXCRETED IN THE URINE, BUT THE 4-HYDROXY METABOLITE IS EXCRETED INTO BILE. THE PHARMACOKINETICS IS THAT OF A TWO-COMPARTMENT SYSTEM, WITH A DISTRIBUTION HALF-LIFE OF LESS THAN 1 HOUR AND AN ELIMINATION HALF-LIFE OF 10 TO 40 HOURS.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 367


AFTER ABSORPTION METHAQUALONE IS TAKEN UP BY ADIPOSE TISSUE & GRADUALLY RELEASED OVER PERIOD OF SEVERAL DAYS. AS IT IS RELEASED IT RAPIDLY UNDERGOES GLUCURONIDE CONJUGATION ... & IS EXCRETED EQUALLY IN URINE & FECES FOR UP TO 6-7 DAYS. IN TOXIC DOSES UNMETABOLIZED METHAQUALONE IS ALSO FOUND IN URINE.

Casarett, L.J., and J. Doull. Toxicology: The Basic Science of Poisons. New York: MacMillan Publishing Co., 1975., p. 649


BLOOD & URINE SAMPLES FROM ACUTELY INTOXICATED PATIENT STUDIED. 4 MAJOR MONOHYDROXYLATED METABOLITES FOUND CONJUGATED IN URINE. 2-METHYL-3-[2-(HYDROXYMETHYL)PHENYL]-4(3H)-QUINAZOLINONE FOUND UNCONJUGATED IN URINE & BLOOD.

KAZYAK L ET AL; J ANAL TOXICOL 3(2): 67 (1979)


URINARY EXCRETION OF 5 C-MONOHYDROXY METABOLITES & METHAQUALONE N-OXIDE MEASURED FOLLOWING ORAL ADMIN OF 250 MG TO GERIATRIC PT. TOTAL EXCRETION OF 6 METABOLITES IN 24 HR WAS APPROX ONE-HALF THAT IN GROUP OF YOUNG, HEALTHY ADULTS.

PMID:668786 REYNOLDS CN ET AL; EUR J CLIN PHARMACOL 13(4): 285 (1978)


For more Absorption, Distribution and Excretion (Complete) data for METHAQUALONE (10 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

MORE THAN 99% OF THE DRUG IS METABOLIZED BY THE HEPATIC MICROSOMAL SYSTEM, AND 4-HYDROXYMETHAQUALONE AND THE N'-OXIDE ARE THE MAJOR PRIMARY METABOLITES. AT LEAST EIGHT OTHER HYDROXYL METABOLITES ARE FORMED.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 367


YIELDS 3-(3-HYDROXY-2-METHYLPHENYL)-2-METHYL-4(3H)-QUINAZOLINONE, 3-(4-HYDROXY-2-METHYLPHENYL)-2-METHYL-4(3H)-QUINAZOLINONE, & 6-HYDROXY-2-METHYL-3-(O-TOLYL)-4(3H)-QUINAZOLINONE IN MAN. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. M-41


... METHAQUALONE ... GAVE 2-NITROBENZO-ORTHO-TOLUIDIDE ... AS HUMAN URINARY METABOLITE.

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 72


BIOTRANSFORMATION ... WOULD BE EXPECTED TO PROCEED BY HYDROXYLATION, & THIS LARGELY OCCURS IN PRACTICE, WHEN GLUCURONIDES OF ... 2-METHYL-3-(3-HYDROXY-2-METHYLPHENYL)-4(3H)-QUINAZOLINONE, 2-METHYL-3-O-TOLYL-6-HYDROXY-4(3H)-QUINAZOLINONE & 2-METHYL-3-O-TOLYL-8-HYDROXY-4(3H)-QUINAZOLINONE ... EXCRETED IN URINE OF ... RATS.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 156


For more Metabolism/Metabolites (Complete) data for METHAQUALONE (7 total), please visit the HSDB record page.


Methaqualone has known human metabolites that include hydroxy-methaqualone.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.5 Biological Half-Life

2-3 hr /From table/

Amdur, M.O., J. Doull, C.D. Klaasen (eds). Casarett and Doull's Toxicology. 4th ed. New York, NY: Pergamon Press, 1991., p. 942


5.6 Mechanism of Action

IN ADDITION TO SEDATIVE-HYPNOTIC PROPERTIES ... /IT/ POSSESSES ANTICONVULSANT, ANTISPASMODIC, LOCAL ANESTHETIC, & WEAK ANTIHISTAMINIC PROPERTIES. IN HIGH DOSES IT SELECTIVELY DEPRESSES POLYSYNAPTIC PATHWAYS IN THE SPINAL CORD. THE DRUG HAS ANTITUSSIVE ACTIVITY COMPARABLE TO THAT OF CODEINE ... IT LACKS ANALGESIC ACTIVITY.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 367


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