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Methaqualone: Difference between revisions
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'''Methaqualone''' (brand name '''Quaalude''' in the US and '''Mandrax''' in the UK) is a central nervous system (CNS) [[psychoactive class::depressant]] of the [[chemical class::quinazolinone]] class that acts as a [[sedative]] and [[hypnotic]]. The sedative–hypnotic activity of methaqualone was first noted by researchers in the 1950s and in 1962 methaqualone itself was patented in the US by Wallace and Tiernan.<ref> | '''Methaqualone''' (brand name '''Quaalude''' in the US and '''Mandrax''' in the UK) is a central nervous system (CNS) [[psychoactive class::depressant]] of the [[chemical class::quinazolinone]] class that acts as a [[sedative]] and [[hypnotic]]. The sedative–hypnotic activity of methaqualone was first noted by researchers in the 1950s and in 1962 methaqualone itself was patented in the US by Wallace and Tiernan.<ref>{{Citation | vauthors=((Vithal, S. B.)), ((Campanella, L. A.)), ((Hays, E. E.)) | title=Hydroxy and alkoxy aryl quinazolinones | url=https://patents.google.com/patent/US3135659A/en}}</ref> Its use peaked in the early 1970s as a hypnotic, for the treatment of insomnia, and as a [[sedative]] and [[muscle relaxant]]. It is still produced and used clandestinely as a recreational drug throughout the world. The drug was popular in the 1970s with hippies and in the disco club scene, known as '''ludes''' (from "quaaludes") or '''disco biscuits'''. | ||
==Chemistry== | ==Chemistry== | ||
Methaqualone, or 2-methyl-3-(2-methylphenyl)-4(3H)-quinazolinone, is a compound of the quinazolinone class. Quinazolinone is a bicyclic structure containing a phenyl ring bound to another six-membered ring with two nitrogen members and a ketone group bound to R<sub>4</sub>. In methaqualone, this structure is substituted at R<sub>2</sub> with a methyl group. Additionally, methaqualone contains a phenyl ring with a methyl group bound to R<sub>2</sub> which is attached to the quinazolinone structure at R<sub>3</sub>. | Methaqualone, or 2-methyl-3-(2-methylphenyl)-4(3H)-quinazolinone, is a compound of the quinazolinone class. Quinazolinone is a bicyclic structure containing a phenyl ring bound to another six-membered ring with two nitrogen members and a ketone group bound to R<sub>4</sub>. In methaqualone, this structure is substituted at R<sub>2</sub> with a methyl group. Additionally, methaqualone contains a phenyl ring with a methyl group bound to R<sub>2</sub> which is attached to the quinazolinone structure at R<sub>3</sub>. | ||
Methaqualone is also known as 3,4-dihydro-2-methyl-4-oxo-3-o-tolylquinazoline, 2-methyl-3-(2-methylphenyl)-4-(3H)-quinazolinone, Metholquizolone, QZ-2, 2-Methyl-3-o-tolyl-4(3H)-quinazolinone, RIC-272, TR-495 and Quaalude. The Methaqualone LD<sub>50</sub> for mice is 1250 mg/kg, and for rats both the values 255 and 326 mg/kg has been published. A common human dose (as sedative) is 150 mg for a 75 kg person.<ref>{{Citation | title=Methaqualone (Quaalude) Synthesis - [www.rhodium.ws] | url=https://chemistry.mdma.ch/hiveboard/rhodium/quaalude.html}}</ref> | |||
==Pharmacology== | ==Pharmacology== | ||
Despite prior speculation, a 2015 study demonstrates that methaqualone exhibits distinct functional properties at the [[GABA]] [[receptor]] sites compared with other allosteric modulators, and it mediates these through a different mechanism than the [[barbiturates]] and [[benzodiazepines]] that it historically has been lumped together with.<ref name="ncbi qualuude study">A Multifaceted GABAA Receptor Modulator: Functional Properties and Mechanism of Action of the Sedative-Hypnotic and Recreational Drug Methaqualone (Quaalude) | Despite prior speculation, a 2015 study demonstrates that methaqualone exhibits distinct functional properties at the [[GABA]] [[receptor]] sites compared with other allosteric modulators, and it mediates these through a different mechanism than the [[barbiturates]] and [[benzodiazepines]] that it historically has been lumped together with.<ref name="ncbi qualuude study">{{cite journal | vauthors=((Hammer, H.)), ((Bader, B. M.)), ((Ehnert, C.)), ((Bundgaard, C.)), ((Bunch, L.)), ((Hoestgaard-Jensen, K.)), ((Schroeder, O. H.-U.)), ((Bastlund, J. F.)), ((Gramowski-Voß, A.)), ((Jensen, A. A.)) | journal=Molecular Pharmacology | title=A Multifaceted GABAA Receptor Modulator: Functional Properties and Mechanism of Action of the Sedative-Hypnotic and Recreational Drug Methaqualone (Quaalude) | volume=88 | issue=2 | pages=401–420 | date= August 2015 | issn=1521-0111 | doi=10.1124/mol.115.099291}}</ref> These distinctions could contribute to the reported differences in the in vivo effects induced by methaqualone and classic CNS [[depressants]]. In any case, the multifaceted functionality of methaqualone at [[GABA#Drugs_targeting_GABA-A|GABA<sub>A</sub>]] receptors seems to be at the root of its clinical efficacy, as well as the addiction liability and recreational use associated with the drug.<ref name="ncbi qualuude study" /> | ||
Methaqualone is a member of the class of quinazolines that is quinazolin-4-one substituted at positions 2 and 3 by methyl and o-tolyl groups respectively. A depressant that increases the activity of the GABA receptors in the brain and nervous system, it is used as a sedative and hypnotic medication. It has a role as a GABA agonist and a sedative.<ref> | Methaqualone is a member of the class of quinazolines that is quinazolin-4-one substituted at positions 2 and 3 by methyl and o-tolyl groups respectively. A depressant that increases the activity of the GABA receptors in the brain and nervous system, it is used as a sedative and hypnotic medication. It has a role as a GABA agonist and a sedative.<ref>{{Citation | title=methaqualone (CHEBI:6821) | url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6821}}</ref> | ||
It could be speculated that despite differences in targeted receptors, methaqualone essentially produces a variety of effects by binding to its receptor sites and magnifying the efficiency and effects of the [[neurotransmitter]] gamma aminobutyric acid (GABA) by acting on its receptors. As this site is the most prolific inhibitory receptor set within the brain, its modulation would explain the resulting [[sedating]] or [[anxiety suppression|calming]] effects which ensue. | It could be speculated that despite differences in targeted receptors, methaqualone essentially produces a variety of effects by binding to its receptor sites and magnifying the efficiency and effects of the [[neurotransmitter]] gamma aminobutyric acid (GABA) by acting on its receptors. As this site is the most prolific inhibitory receptor set within the brain, its modulation would explain the resulting [[sedating]] or [[anxiety suppression|calming]] effects which ensue. | ||
Although some early research indicated it may operate at the benzodiazepine receptor site, this doesn’t appear to be the case. More recent evaluations have pointed to a different [[GABA#Drugs_targeting_GABA-A|GABA<sub>A</sub>]] modulatory site located on the transmembrane b(+)/a(-) subunit interface. | |||
==Subjective effects== | ==Subjective effects== | ||
{{Preamble/SubjectiveEffects}} | {{Preamble/SubjectiveEffects}} | ||
{{effects/base | {{effects/base | ||
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*'''[[Effect::Dream potentiation]]''' | *'''[[Effect::Dream potentiation]]''' | ||
*'''[[Effect::Analysis suppression]]''' | *'''[[Effect::Analysis suppression]]''' | ||
*'''[[Effect::Cognitive euphoria | *'''[[Effect::Cognitive euphoria]]''' | ||
*'''[[Effect::Compulsive redosing]]''' | *'''[[Effect::Compulsive redosing]]''' | ||
*'''[[Effect::Increased libido]]''' | *'''[[Effect::Increased libido]]''' | ||
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}} | }} | ||
===Experience reports=== | ===Experience reports=== | ||
{{Experience reports|erowid_experience_substance_label=Methaqualone}} | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
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*'''Austria:''' Methaqualone is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}} | *'''Austria:''' Methaqualone is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}} | ||
*'''Canada:''' Methaqualone is Schedule III in Canada, meaning it requires a prescription or license to legally possess.{{citation needed}} | *'''Canada:''' Methaqualone is Schedule III in Canada, meaning it requires a prescription or license to legally possess.{{citation needed}} | ||
*'''Germany:''' Methaqualone is controlled under BtMG Anlage II, making it illegal to manufacture, import, possess, sell, or transfer it without a license.<ref>http://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html</ref> | *'''Germany:''' Methaqualone is controlled under BtMG Anlage II, making it illegal to manufacture, import, possess, sell, or transfer it without a license.<ref>{{Citation | title=Anlage II BtMG - Einzelnorm | url=http://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html}}</ref> | ||
*'''Switzerland:''' Methaqualone is a controlled substance specifically named under Verzeichnis A. Medicinal use is permitted.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | *'''Switzerland:''' Methaqualone is a controlled substance specifically named under Verzeichnis A. Medicinal use is permitted.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | ||
*'''United Kingdom:''' Methaqualone is a Class B drug.<ref> | *'''United Kingdom:''' Methaqualone is a Class B drug.<ref>{{Citation | vauthors=((Participation, E.)) | title=Misuse of Drugs Act 1971 | url=https://www.legislation.gov.uk/ukpga/1971/38/schedule/2}}</ref> | ||
*'''United States:''' Methaqualone is a Schedule I drug, and is illegal to possess without a license.<ref>http://www.drugs.com/article/csa-schedule-1.html</ref> | *'''United States:''' Methaqualone is a Schedule I drug, and is illegal to possess without a license.<ref>http://www.drugs.com/article/csa-schedule-1.html</ref> | ||
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[[Category:quinazolinone]] | [[Category:quinazolinone]] | ||
[[Category:Depressant]] | [[Category:Depressant]] | ||
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