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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''' (also known by the brand name '''Sustiva''') is a non-nucleotide reverse transcriptase inhibitor used in the treatment and prevention of human immunodeficiency virus infections type 1 (HIV-1). Efavirenz is notable for having a strange array of effects, many resembling [[psychedelics]], as well as an extremely unique pharmacological profile and structure.
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 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. The empirical formula of efavirenz is C<sub>14</sub>H<sub>9</sub>ClF<sub>3</sub>NO<sub>2</sub> and has a molar mass of 315.675 grams per mole.<ref> Efavirenz PubChem | https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=64139</ref>
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).. 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==
The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|contributors]]. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.
{{Preamble/SubjectiveEffects}}
===Physical effects===
{{effects/base
|{{effects/physical|
*'''[[Effect::Physical euphoria]]''' - This effect is generally quite mild.
*'''[[Effect::Physical euphoria]]''' - This effect is generally quite mild.
*'''[[Effect::Psychosis]]''' - At very high doses, efavirenz may cause a psychotic state.
*'''[[Effect::Unity and interconnectedness]]''' - This effect is generally quite mild.
*'''[[Effect::Confusion]]'''
*'''[[Effect::Introspection]]'''
*'''[[Effect::Dream potentiation]]''' - At non-recreational doses, efavirenz often induces strange dreams.
*'''[[Effect::Disinhibition]]'''
===Visual effects===
====Enhancements====
====Enhancements====
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Colour enhancement]]'''
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*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::Internal hallucinations]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]'')
*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'')
*'''[[Effect::External hallucinations]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]'')
*'''[[Effect::External hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'')
Efavirenz has a [[Toxicity::low toxicity]] relative to dose. Like many HIV medications, efavirenz may cause liver toxicity at high doses or after chronic use.
{{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]].
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
===Tolerance and addiction potential===
===Tolerance and addiction potential===
Efavirenz is [[Addiction potential::not known to be habit-forming]]. While developing a tolerance to efavirenz is extremely rare, abusing efavirenz may cause HIV to become resistant to the drug and increase the viral load in patients with HIV.
Efavirenz is [[Addiction potential::not known to be habit-forming]]. While developing a tolerance to efavirenz is extremely rare, abusing efavirenz may cause HIV to become resistant to the drug and increase the viral load in patients with HIV.
===Dangerous interactions===
===Dangerous interactions===
As efavirenz may cause hepatoxicity at high doses or after chronic use, it is not recommended to take this substance concurrently with other substances that may cause hepatoxicity. Efavirenz is an inducer of the CYP2B6 and CYP3A4 enzymes of the cytochrome P450 system, and as a result may change the metabolism of drugs metabolized by them. Consuming garlic may decrease serum levels of efavirenz.
As efavirenz may cause hepatoxicity at high doses or after chronic use, it is not recommended to take this substance concurrently with other substances that may cause hepatoxicity. Efavirenz is an inducer of the CYP2B6 and CYP3A4 enzymes of the cytochrome P450 system, and as a result may change the metabolism of drugs metabolized by them. Consuming garlic may decrease serum levels of efavirenz.
====[[Serotonin syndrome]] risk====
====[[Serotonin syndrome]] risk====
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{{DangerousInteractions/SerotoninSyndrome}}
{{DangerousInteractions/SerotoninSyndrome}}
==Legal issues==
==Legal status==
{{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>
*'''Switzerland''': Efavirenz is listed as a "Abgabekategorie A" pharmaceutical, which requires a prescription.{{citation needed}}
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
Efavirenz (sold by the brand name Sustiva) is an antiretroviral medication used in the treatment and prevention of HIV/AIDS.[2] 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.[3]
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. [4][5][6]
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).. Efavirenz is chemically described as (S)-6-chloro-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its empirical formula is C14H9ClF3NO2.
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.
Unlike most non-nucleotide reverse transcriptase inhibitors, efavirenz is also a 5-HT2A partial agonist, similar to LSD. Additionally, efavirenz is a serotonin and dopaminereuptake inhibitor and a vesicular monoamine transporter 2 inhibitor. Efavirenz also acts as a GABAA positive allosteric modulator, similar to benzodiazepines and barbiturates.[7] 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.[8]
Subjective effects
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWikicontributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
Efavirenz is not known to be habit-forming. While developing a tolerance to efavirenz is extremely rare, abusing efavirenz may cause HIV to become resistant to the drug and increase the viral load in patients with HIV.
Dangerous interactions
As efavirenz may cause hepatoxicity at high doses or after chronic use, it is not recommended to take this substance concurrently with other substances that may cause hepatoxicity. Efavirenz is an inducer of the CYP2B6 and CYP3A4 enzymes of the cytochrome P450 system, and as a result may change the metabolism of drugs metabolized by them. Consuming garlic may decrease serum levels of efavirenz.
Efavirenz is a weak serotonin reuptake inhibitor, so it is possible that combining heavy doses of efavirenz and the substances listed below may result in serotonin syndrome.
Combinations with the following substances can cause dangerously high serotonin levels. Serotonin syndrome requires immediate medical attention and can be fatal if left untreated.
↑Apostolova, N., Funes, H. A., Blas-Garcia, A., Galindo, M. J., Alvarez, A., Esplugues, J. V. (October 2015). "Efavirenz and the CNS: what we already know and questions that need to be answered". The Journal of Antimicrobial Chemotherapy. 70 (10): 2693–2708. doi:10.1093/jac/dkv183. ISSN1460-2091.
. eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. PMID 16051647.