Methaqualone
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| Systematic (IUPAC) name | |
|---|---|
| '2-methyl-3-o-tolyl-4(3H)-quinazolinone; 3,4-dihydro-2-methyl-4-oxo-3-o-tolylquinazoline; 2-methyl-3-(2-methylphenyl)-4-(3H)-quinazolinone |
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| Identifiers | |
| CAS number | 72-44-6 |
| ATC code | N05CM01 |
| PubChem | 6292 |
| DrugBank | ? |
| ChemSpider | 6055 |
| Chemical data | |
| Formula | C16H14N2O |
| Mol. mass | 250.30 |
| Physical data | |
| Melt. point | 113 °C (235 °F) |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | ? |
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Methaqualone is a sedative drug that is similar in effect to barbiturates, a general CNS depressant. Its use peaked in the 1960s and 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 (particularly in the 1970s in North America) or as Mandrax (methaqualone 250 mg combined with diphenhydramine 5 mg). In the 2000s, it is widely used in South Africa, "the largest abuser of Mandrax in the world."[1]
Methaqualone was first synthesised in India in 1951 by Indra Kishore Kacker and Syed Hussain Zaheer,[2][3] and was soon introduced to Japanese and European consumers as a safe barbiturate substitute.[citation needed] By 1965 it was the most commonly prescribed sedative in Britain, where it has been sold legally under the names Malsed, Malsedin, and Renoval. In 1965 Methaqualone and an antihistamine combination were sold as the sedative drug Mandrax by Rousell Laboratories. At about the same time (1965) it was starting to become a popular recreational drug named mandies or mandrake. In 1972 it was the sixth best selling sedative on the market in the United States,[4] where it was legally sold by the name of Quaalude, and "luding out" was a popular college pastime.[5]
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[edit] Effects
Usual effects include relaxation, euphoria, and drowsiness, also reducing heart rate, respiration, increased sexual arousal (aphrodisia) and parasthesias (Numbness of the fingers and toes). Bigger doses can bring about respiratory depression, slurred speech, headache and photophobia (pain in the eyes when exposed to light).
An overdose can cause delirium, convulsions, hypertonia, hyperreflexia, vomiting, renal insufficiency, coma, and death through cardiac or respiratory arrest. It resembles barbiturate poisoning, but with increased motor difficulties and a lower incidence of cardiac or respiratory depression. Toxicity is treated with diazepam and sometimes other anticonvulsants.
This is one of the drugs taken in his life time by Elvis Aaron Presley ( January 8, 1935 - August 16, 1977 ), which many believe contributed to his death at age 42.
[edit] Recreational use
Quaaludes became increasingly popular as a recreational drug in the late 1960s and early 1970s. The drug was used during sexual activity because of heightened sensitivity coupled with relaxation and euphoria. The drug was more tightly regulated in Britain under the Misuse of Drugs Act 1971 and in the U.S. from 1973. It was withdrawn from many developed markets in the 1980s, being made a Schedule I drug in the US in 1984.
Smoking methaqualone, either alone or as an adulterant added to various legal and illegal smoking mixtures, gained popularity in the United States during the mid-1970s. When smoked, methaqualone gives the user an immediate trance-like euphoria that quickly wears off. Because the various binders and inert ingredients that were contained in the pill form were toxic when smoked, this practice was roundly decried by the medical community as a serious health risk. Smoking methaqualone pills can lead to emphysema and other chronic lung disorders, most notably talcosis.
[edit] South Africa
Commonly known as Mandrax, M-pills or buttons, it is not taken orally but is crushed and mixed in a pipe (or in the neck of a broken bottle) with marijuana. Methaqualone is one of the most commonly used hard drugs in South Africa.[1][6] The low price (South African Rand R30.00 average, which is about USD $3.02 or EUR €2.34 (as of March 13 2009))[citation needed] of methaqualone together with the ready availability of cheap, low-grade marijuana make it (in addition to methamphetamine and temazepam) the preferred hard drug of the low-income section of South African society.[1]
Methaqualone is no longer legally produced, so methaqualone for the South African market is manufactured either in India or in South Africa itself — or in other African countries.[7]
In the feature film comedy " Dick " ( 1999 ), starring Dan Hedaya ( 1940 - ), Michelle Williams ( 1980 - ) and Kirsten Dunst( 1982 - ), the character Larry Jobs, brother to Dunst's character, and played by Devon Gummershall ( 1978 - ), who is a stoner, is claimed to have later ( after Watergate ) invented Qualuudes, but obviously this is not true, although meant as an amusing aside.
[edit] See also
[edit] References
- ^ a b c "Mandrax" (in English). DrugAware. Reality Media. 2003. http://www.drugaware.co.za/mandrax.html. Retrieved 2009-08-13.
- ^ p. 142, A survey of reported synthesis of methaqualone and some positional and structural isomers, Etienne F. van Zyl, Forensic Science International 122, #2-3 (1 November 2001), pp. 142–149, doi:10.1016/S0379-0738(01)00484-4.
- ^ 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.
- ^ GC/MS Assays for Abused Drugs in Body fluids, p. 39
- ^ Scheindlin, Stanley (2005). "Antimalarials: Shortages and Searches". Molecular Interventions 5 (5): 268-272. doi:.
- ^ McCarthy G, Myers B, Siegfried N. Treatment for methaqualone dependence in adults. Cochrane Database of Systematic Reviews. 2005 Apr 18;(2):CD004146. PMID 15846700
- ^ van Zyl EF (November 2001). "A survey of reported synthesis of methaqualone and some positional and structural isomers". Forensic Sci. Int. 122 (2-3): 142–9. PMID 11672968. http://linkinghub.elsevier.com/retrieve/pii/S0379-0738(01)00484-4.
- Bioavailability of Methaqualone
Smyth RD, Lee JK, Polk A, Chemburkar PB, Savacool AM (October 1973). "Bioavailability of methaqualone". J Clin Pharmacol 13 (10): 391–400. PMID 4490663. http://jcp.sagepub.com/cgi/pmidlookup?view=long&pmid=4490663.
Nayak RK, Smyth RD, Chamberlain JH, et al. (April 1974). "Methaqualone pharmacokinetics after single- and multiple-dose administration in man". J Pharmacokinet Biopharm 2 (2): 107–21. PMID 4427217.
Chemburkar PB, Smyth RD, Buehler JD, et al. (April 1976). "Correlation between dissolution characteristics and absorption of methaqualone from solid dosage forms". J Pharm Sci 65 (4): 529–33. PMID 1271252.
[edit] External links
- The Meth Epidemic Frontline discusses quaaludes as part of the history of methamphetamine
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