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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| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Schedule III (CA) Schedule I (US) |
| Identifiers | |
| CAS number | 72-44-6  |
| ATC code | N05CM01 |
| PubChem | CID 6292 |
| DrugBank | DB04833 |
| ChemSpider | 6055 |
| UNII | 7ZKH8MQW6T |
| KEGG | D00557 |
| ChEMBL | CHEMBL282052 |
| Chemical data | |
| Formula | C16H14N2O |
| Mol. mass | 250.30 g/mol |
| SMILES | eMolecules & PubChem |
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| Physical data | |
| Melt. point | 113 °C (235 °F) |
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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.[1] 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 (
/ˈkweɪljuːdz/ kway-lewdz), 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,[2] 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.
Methaqualone was first synthesized in India in 1951 by Indra Kishore Kacker and Syed Hussain Zaheer,[3][4] 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 a Methaqualone/antihistamine combination was sold as the sedative drug Mandrax, by Roussel Laboratories (now part of Sanofi-Aventis). At about the same time, it was becoming a popular recreational drug (called "mandies" or "mandrake" or "mandrix"). In 1972 it was the sixth-bestselling sedative in the USA,[5] where it was legal under the brand name Quaalude; at that time "luding out" was a popular college pastime. This is the similar effect of an alcoholic blackout with no recollection of events.[6]
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[edit] Effects
Effects can include euphoria, drowsiness, reduced heart rate, reduced respiration, increased sexual arousal (aphrodisia), and paresthesias (numbness of the fingers and toes). Larger doses can bring about respiratory depression, slurred speech, headache, and photophobia (a symptom of excessive sensitivity to light).
An overdose can cause delirium, convulsions, hypertonia, hyperreflexia, vomiting, renal failure, 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.[citation needed]
[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 and lowered inhibition coupled with relaxation and euphoria.[citation needed]
The drug was often used by people who went dancing at glam rock clubs in the early 1970s and at discos in the late 1970s. (One slang term for Quaaludes was disco biscuits.) In the mid 1970s there were bars in Manhattan called juice bars that only served non-alcoholic drinks that catered to people who liked to dance on methaqualone.[7]
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 early 1980s (in 1982 in the United States), being made a Schedule I drug in the U.S. in 1984.
Smoking methaqualone, either by itself or as an adulterant added to various legal and illegal smoking mixtures, gained popularity in the US among a few during the mid-1970s. 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
Methaqualone is one of the most commonly used hard drugs in South Africa.[2][8] Commonly known as Mandrax, M-pills, buttons, or smarties, it is not taken orally but is crushed and mixed in a pipe with marijuana. The low price (South African Rand 30 R average, which is about $4) of methaqualone together with readily available cheap, low-grade marijuana (in addition to methamphetamine and temazepam) makes it the preferred hard drug of the lower-income sections of South African society.[2]
[edit] Slang terms
Methaqualone was manufactured in the United States under the name Quaalude by the pharmaceutical giants "Rorer" and "Lemmon" with the numbers 714 stamped on the tablet, so people often referred to Quaaludes as 714's,"Lemmons", or "Lemmon 7s". After the legal manufacture of the drug ended in the United States in 1982, underground laboratories in Mexico continued illegal manufacture of methaqualone all through the 1980s, continuing the use of the "714" stamp, until their popularity waned in the early 1990s.
Other widely used slang terms (given here in the plural) used for the drug methaqualone included: furies, ludes, mandrakes, quales, quas, quacks, quads, soaps, soapers, sopes, and super soper. A user can be commonly referred to as "ducking out." [7]
[edit] See also
- Methaqualone in popular culture
- Cloroqualone
- Diproqualone
- Etaqualone
- Mebroqualone
- Mecloqualone
- Methylmethaqualone
- Nitromethaqualone
[edit] References
- ^ US Patent 3135659 - Hydroxy and Alkoxy Aryl Quinazolones
- ^ a b c "Mandrax". 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:10.1124/mi.5.5.2. PMID 16249521.
- ^ a b Methaqualone:
- ^ McCarthy G, Myers B, Siegfried N. Treatment for methaqualone dependence in adults. Cochrane Database of Systematic Reviews. 2005 Apr 18;(2):CD004146. PMID 15846700
[edit] External links
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