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Efavirenz: Difference between revisions

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{{SubstanceBox/Efavirenz}}
{{SubstanceBox/Efavirenz}}


'''Efavirenz''' (sold by the brand name '''Sustiva''') is an antiretroviral medication used in the treatment and prevention of HIV/AIDS.<ref>Vrouenraets, S. M., Wit, F. W., Tongeren, J. V., & Lange, J. M. (2007). Efavirenz: a review. Expert Opinion on Pharmacotherapy, 8(6), 851-871. https://doi.org/10.1517/14656566.8.6.851</ref> It is notable for being able to produce [[psychedelic]] and [[hallucinogenic]] effects despite possessing an extremely novel pharmacological profile and chemical structure not shared with any other psychedelic substance.
'''Efavirenz''' (sold by the brand name '''Sustiva''') is an antiretroviral medication used in the treatment and prevention of HIV/AIDS.<ref>
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{{cite journal | vauthors=((Vrouenraets, S. M.)), ((Wit, F. W.)), ((Tongeren, J. van)), ((Lange, J. M.)) | journal=Expert Opinion on Pharmacotherapy | title=Efavirenz: a review | volume=8 | issue=6 | pages=851–871 | date= April 2007 | url=http://www.tandfonline.com/doi/full/10.1517/14656566.8.6.851 | issn=1465-6566 | doi=10.1517/14656566.8.6.851}}</ref> It is notable for being able to produce [[psychedelic]] and [[hallucinogenic]] effects despite possessing an extremely novel pharmacological profile and chemical structure not shared with any other psychedelic substance.


Efavirenz was approved for medical use in the United States in 1998.{{citation needed}} It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.<ref>{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|accessdate=8 December 2016|date=April 2015|deadurl=no|archiveurl=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archivedate=13 December 2016|df=}}</ref>
Efavirenz was approved for medical use in the United States in 1998.{{citation needed}} It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.<ref>{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|accessdate=8 December 2016|date=April 2015|deadurl=no|archiveurl=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archivedate=13 December 2016|df=}}</ref>


Recreational use of efavirenz for its hallucinogenic and dissociative effects has been reported in South Africa. The tablets are crushed and smoked in a mixture known as ''whoonga'' and ''nyaope''.<ref>[http://news.bbc.co.uk/2/hi/africa/7768059.stm Getting high on HIV drugs in S Africa. BBC News, 8 December 2008.] {{webarchive|url=https://web.archive.org/web/20081209053431/http://news.bbc.co.uk/2/hi/africa/7768059.stm |date=9 December 2008 }}</ref><ref>[http://www.abcnews.go.com/Health/MindMoodNews/story?id=7227982&page=1 'No Turning Back': Teens Abuse HIV Drugs. ABC News, April 6, 2009.] {{webarchive|url=https://web.archive.org/web/20090408041457/http://abcnews.go.com/Health/MindMoodNews/story?id=7227982&page=1 |date=April 8, 2009 }}</ref><ref>[https://www.youtube.com/watch?v=W7BCi5ax7jk Getting High On HIV Medication] {{webarchive|url=https://web.archive.org/web/20140411153925/https://www.youtube.com/watch?v=W7BCi5ax7jk |date=2014-04-11 }} Vice 7.04.2014.</ref>
Recreational use of efavirenz for its hallucinogenic and dissociative effects has been reported in South Africa. The tablets are reportedly crushed and smoked in a mixture known as "whoonga" , "nyaope" , and "wonga". A form of black tar heroin. Although current analyses of whoonga samples have yet to confirm the presence efavirenz in the mixture.   <ref>{{Citation | year=2008 | title=Getting high on HIV drugs in S Africa | url=http://news.bbc.co.uk/2/hi/africa/7768059.stm}}</ref><ref>{{Citation | vauthors=((News, A. B. C.)) | title=“No Turning Back”: Teens Abuse HIV Drugs | url=https://abcnews.go.com/Health/MindMoodNews/story?id=7227982&page=1}}</ref><ref>{{Citation | vauthors=((Vice)) | year=2014 | title=Getting High On HIV Medication - Part 1/2 | url=https://www.youtube.com/watch?v=W7BCi5ax7jk}}</ref>


==Chemistry==
==Chemistry==
Unlike most psychedelics, efavirenz is not a [[tryptamine]], [[phenethylamine]] or [[lysergamide]]. Efavirenz is classified as a benzoxazine and has several different moieties which give it a unique pharmacological profile. On the two position of the benzoxazine ring, efavirenz has a ketone attached. Efavirenz also has a trifluoromethyl group as well as a cyclopropane ring.
Unlike most psychedelics, efavirenz is not a [[tryptamine]], [[phenethylamine]] or [[lysergamide]]. Efavirenz is classified as a benzoxazine and has several different moieties which give it a unique pharmacological profile. On the two position of the benzoxazine ring, efavirenz has a ketone attached. Efavirenz also has a trifluoromethyl group as well as a cyclopropane ring.


Efavirenz is a white to slightly pink crystalline powder with a molecular mass of 315.68 g/mol. It is practically insoluble in water (<10 µg/mL).{{citation needed}}
Efavirenz is a white to slightly pink crystalline powder with a molecular mass of 315.68 g/mol. It is practically insoluble in water (<10 µg/mL).. Efavirenz is chemically described as (''S'')-6-chloro-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2''H''-3,1-benzoxazin-2-one. Its empirical formula is C<sub>14</sub>H<sub>9</sub>ClF<sub>3</sub>NO<sub>2</sub>.


==Pharmacology==
==Pharmacology==
Pharmacologically, efavirenz is primarily classified as a non-nucleotide reverse transcriptase inhibitor, or NNRTI. Reverse transcriptase is an enzyme found in several viral species that is a type of DNA polymerase and nuclease that allows viruses like hepatitis and human immunodeficiency virus to transcribe viral RNA into DNA. Efavirenz is considered a non-nucleotide reverse transcriptase inhibitor because it does not have a structure based off of a nucleotide.
Pharmacologically, efavirenz is primarily classified as a non-nucleotide reverse transcriptase inhibitor, or NNRTI. Reverse transcriptase is an enzyme found in several viral species that is a type of DNA polymerase and nuclease that allows viruses like hepatitis and human immunodeficiency virus to transcribe viral RNA into DNA. Efavirenz is considered a non-nucleotide reverse transcriptase inhibitor because it does not have a structure based off of a nucleotide.


Unlike most non-nucleotide reverse transcriptase inhibitors, efavirenz is also a 5-HT<sub>2A</sub> partial agonist, similar to [[LSD]]. Additionally, efavirenz is a [[serotonin]] and [[dopamine]] [[reuptake inhibitor]] and a vesicular monoamine transporter 2 inhibitor. Efavirenz also acts as a [[GABA]]<sub>A</sub> positive allosteric modulator, similar to [[benzodiazepines]] and [[barbiturates]].<ref> Neuropsychopharmacology | http://www.nature.com/npp/journal/v38/n12/full/npp2013135a.html</ref> Efavirenz has a bioavailability of about 40-45% when it is taken on an empty stomach.
Unlike most non-nucleotide reverse transcriptase inhibitors, efavirenz is also a 5-HT<sub>2A</sub> partial agonist, similar to [[LSD]]. Additionally, efavirenz is a [[serotonin]] and [[dopamine]] [[reuptake inhibitor]] and a vesicular monoamine transporter 2 inhibitor. Efavirenz also acts as a [[GABA]]<sub>A</sub> positive allosteric modulator, similar to [[benzodiazepines]] and [[barbiturates]].<ref>{{cite journal | vauthors=((Gatch, M. B.)), ((Kozlenkov, A.)), ((Huang, R.-Q.)), ((Yang, W.)), ((Nguyen, J. D.)), ((González-Maeso, J.)), ((Rice, K. C.)), ((France, C. P.)), ((Dillon, G. H.)), ((Forster, M. J.)), ((Schetz, J. A.)) | journal=Neuropsychopharmacology | title=The HIV Antiretroviral Drug Efavirenz has LSD-Like Properties | volume=38 | issue=12 | pages=2373–2384 | date= November 2013 | url=https://www.nature.com/articles/npp2013135 | issn=1740-634X | doi=10.1038/npp.2013.135}}</ref> Efavirenz has a bioavailability of about 40-45% when it is taken on an empty stomach.


Efavirenz is known to cause a false-positive for [[cannabis]] on some urine tests.<ref> http://clinchem.aaccjnls.org/content/52/5/896 </ref>
Efavirenz is known to cause a false-positive for [[cannabis]] on some urine tests.<ref>{{cite journal | vauthors=((Rossi, S.)), ((Yaksh, T.)), ((Bentley, H.)), ((Brande, G. van den)), ((Grant, I.)), ((Ellis, R.)) | journal=Clinical Chemistry | title=Characterization of Interference with 6 Commercial Δ9-Tetrahydrocannabinol Immunoassays by Efavirenz (Glucuronide) in Urine | volume=52 | issue=5 | pages=896–897 | date=1 May 2006 | url=https://academic.oup.com/clinchem/article/52/5/896/5626853 | issn=0009-9147 | doi=10.1373/clinchem.2006.067058}}</ref>


==Subjective effects==
==Subjective effects==
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==Toxicity and harm potential==
==Toxicity and harm potential==
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
Efavirenz has a [[Toxicity::low toxicity]] relative to dose. Like many HIV medications, efavirenz [[Toxicity::may cause liver toxicity at high doses or after chronic use]].
Efavirenz has a [[Toxicity::low toxicity]] relative to dose. Like many HIV medications, efavirenz [[Toxicity::may cause liver toxicity at high doses or after chronic use]].


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{{legalStub}}
{{legalStub}}
Efavirenz is not known to be illegal in any jurisdictions, and is considered a prescription only medication.
Efavirenz is not known to be illegal in any jurisdictions, and is considered a prescription only medication.
*'''Germany''': Efavirenz is a prescription only medicine, according to Anlage 1 AMVV.<ref>{{cite web|url=https://www.gesetze-im-internet.de/amvv/anlage_1.html|title=Anlage 1 AMVV|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref>
*'''Germany''': Efavirenz is a prescription only medicine, according to Anlage 1 AMVV.<ref>{{cite web|url=https://www.gesetze-im-internet.de/amvv/anlage_1.html|title=Anlage 1 AMVV|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref>
*'''Switzerland''': Efavirenz is listed as a "Abgabekategorie A" pharmaceutical, which requires a prescription.{{citation needed}}
*'''Switzerland''': Efavirenz is listed as a "Abgabekategorie A" pharmaceutical, which requires a prescription.{{citation needed}}


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Hallucinogen]]
*[[Hallucinogen]]
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==External links==
==External links==
*[https://en.wikipedia.org/wiki/Efavirenz Efavirenz (Wikipedia)]
*[https://en.wikipedia.org/wiki/Efavirenz Efavirenz (Wikipedia)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=2802 Efavirenz (Isomer Design)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=2802 Efavirenz (Isomer Design)]
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<references />
<references />


[[Category:Psychoactive substance]]
[[Category:Psychedelic]]
[[Category:Psychedelic]]
[[Category:Benzoxazine]]
[[Category:Benzoxazine]]
[[Category:Carbamate]]
[[Category:Carbamate]]
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