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>~~US Patent 3135659 –~~ Hydroxy and ~~Alkoxy Aryl Quinazolones~~</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.

'''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==

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 R4. In methaqualone, this structure is substituted at R2 with a methyl group. Additionally, methaqualone contains a phenyl ring with a methyl group bound to R2 which is attached to the quinazolinone structure at R3.

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 LD50 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>https://chemistry.mdma.ch/hiveboard/rhodium/quaalude.html</ref>

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 LD50 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==

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) ~~(PubMed~~.~~gov / NCBI) | http:/~~/~~www~~.~~ncbi~~.~~nlm.nih.gov/pubmed/26056160~~</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|GABAA]] 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" />

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|GABAA]] 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>~~http~~://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6821</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.

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 ~~GABAA~~ modulatory site located on the transmembrane b(+)/a(-) subunit interface.

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|GABAA]] modulatory site located on the transmembrane b(+)/a(-) subunit interface.

==Subjective effects==

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}}

===Experience reports===

~~There are currently no anecdotal~~ reports ~~which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:~~

{{Experience reports|erowid_experience_substance_label=Methaqualone}}

*[https://erowid.org/experiences/subs/exp_Methaqualone.shtml Erowid Experience Vaults: Methaqualone]

==Toxicity and harm potential==

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*'''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}}

*'''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>

*'''United Kingdom:''' Methaqualone is a Class B drug.<ref>~~http~~://www.legislation.gov.uk/ukpga/1971/38/schedule/2</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>

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[[Category:quinazolinone]]

[[Category:Depressant]]

@@ Line 3: / Line 3: @@
 {{SubstanceBox/Methaqualone}}
-'''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>US Patent 3135659 – Hydroxy and Alkoxy Aryl Quinazolones</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.
+'''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==
 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>https://chemistry.mdma.ch/hiveboard/rhodium/quaalude.html</ref>
+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==
-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) (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/26056160</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" />
+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>http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6821</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.
-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 GABAA modulatory site located on the transmembrane b(+)/a(-) subunit interface.
+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==
@@ Line 57: / Line 57: @@
 }}
 ===Experience reports===
-There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
+{{Experience reports|erowid_experience_substance_label=Methaqualone}}
-*[https://erowid.org/experiences/subs/exp_Methaqualone.shtml Erowid Experience Vaults: Methaqualone]
 ==Toxicity and harm potential==
@@ Line 86: / Line 84: @@
 *'''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}}
-*'''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>
-*'''United Kingdom:''' Methaqualone is a Class B drug.<ref>http://www.legislation.gov.uk/ukpga/1971/38/schedule/2</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>
@@ Line 111: / Line 109: @@
 [[Category:quinazolinone]]
 [[Category:Depressant]]
+{{#set:Featured=true}}