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1cP-LSD: Difference between revisions

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==History and culture==
==History and culture==
Although formal documentation does not appear to have been published, 1cP-LSD is believed to have been first discovered and synthesized in the Netherlands in 2019. It first appeared on the online research chemical market in July that same year.<ref>{{cite web|title=1cP-LSD|publisher=Google Trends|access-date=July 14, 2020|url=https://trends.google.com/trends/explore?date=all&q=1cp-lsd}}</ref>  
Although formal documentation does not appear to have been published, 1cP-LSD was first discovered and synthesized in the Netherlands somewhere in 2015. It first appeared on the online research chemical market in July that same year.<ref>{{cite web|title=1cP-LSD|publisher=Google Trends|access-date=July 14, 2020|url=https://trends.google.com/trends/explore?date=all&q=1cp-lsd}}</ref>


1cP-LSD was released shortly after the prohibition of 1P-LSD in Germany. It is part of a larger series of designer LSD analogs that have appeared on the research chemical market since the mid-2010s. These include [[AL-LAD]], [[ETH-LAD]], and [[ALD-52]]. In July 2021, Germany banned 1cP-LSD, and immediately thereafter [[1V-LSD]] appeared on the market as its replacement.{{citation needed}}
1cP-LSD was released shortly after the prohibition of 1P-LSD in Germany. It is part of a larger series of designer LSD analogs that have appeared on the research chemical market since the mid-2010s. These include [[AL-LAD]], [[ETH-LAD]], and [[ALD-52]]. In July 2021, Germany banned 1cP-LSD, and immediately thereafter [[1V-LSD]] appeared on the market as its replacement.{{citation needed}}
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The structure of 1cP-LSD contains a polycyclic group featuring a bicyclic hexahydro indole bound to a bicyclic quinoline group. At carbon 8 of the quinoline, an N,N-diethyl carboxamide is bound.
The structure of 1cP-LSD contains a polycyclic group featuring a bicyclic hexahydro indole bound to a bicyclic quinoline group. At carbon 8 of the quinoline, an N,N-diethyl carboxamide is bound.


The properties of the substance 1cP-LSD are described as almost identical to those of the classic LSD 25 and 1P-LSD. However, an alkylcarbonyl group has the empirical formula C4H7O, whereas the cyclopropylcarbonyl group corresponds to a molecular formula of C4H5O. Accordingly, one can not call the cyclopropyl as alkyl radical and thus the substance 1cP-LSD is not affected by the NpSG amending Regulation.<ref>https://rcreviewsin.com/new-lysergamide-1cp-lsd/</ref>
The properties of the substance 1cP-LSD are described as almost identical to those of the classic LSD 25 and 1P-LSD. However, an alkylcarbonyl group has the empirical formula C4H7O, whereas the cyclopropylcarbonyl group corresponds to a molecular formula of C4H5O. Accordingly, one can not call the cyclopropyl as alkyl radical and thus the substance 1cP-LSD is not affected by the NpSG amending Regulation.


==Pharmacology==
==Pharmacology==
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The [[psychedelic]] effects are thought to primarily come from its efficacy at the 5-HT<sub>2A</sub> receptors distributed throughout the brain. 1cP-LSD also likely displays binding activity at a wide range of [[monoamine]] receptors, such as those for [[dopamine]] and [[norepinephrine]]. However, there is currently no data to support these claims.
The [[psychedelic]] effects are thought to primarily come from its efficacy at the 5-HT<sub>2A</sub> receptors distributed throughout the brain. 1cP-LSD also likely displays binding activity at a wide range of [[monoamine]] receptors, such as those for [[dopamine]] and [[norepinephrine]]. However, there is currently no data to support these claims.


Owing to its structural similarity to LSD, the following claims may be hypothesized: most serotonergic psychedelics are not significantly dopaminergic, and 1cP-LSD is therefore assumed to be atypical in this regard. Any agonist activity at the D<sub>2</sub> receptor may contribute to its psychoactive effects in humans.<ref>Marona-Lewicka D, Thisted RA, Nichols DE (July 2005). "Distinct temporal phases in the behavioral pharmacology of LSD: dopamine D2 receptor-mediated effects in the rat and implications for psychosis". ''Psychopharmacology''. '''180''' (3): 427–35. doi:10.1007/s00213-005-2183-9. <nowiki>PMID 15723230</nowiki>. S2CID 23565306.</ref> Additionally, 1cP-LSD likely binds to most serotonin receptor subtypes except for the 5-HT<sub>3</sub> and 5-HT<sub>4</sub> receptors. However, most of these receptors are affected at too low affinity to be sufficiently activated by the brain concentration of approximately 10–20 nM.<ref>Nichols DE (February 2004). "Hallucinogens". ''Pharmacology & Therapeutics''. '''101''' (2): 131–81. doi:10.1016/j.pharmthera.2003.11.002. <nowiki>PMID 14761703</nowiki>.</ref> Recreational doses likely can affect 5-HT<sub>1A</sub>, 5-HT<sub>2A</sub>, 5-HT<sub>2B</sub>, 5-HT<sub>2C</sub>, 5-HT<sub>5A</sub> [in cloned rat tissues]), and 5-HT<sub>6</sub> receptors.
Owing to its structural similarity to LSD, the following claims may be hypothesized: most serotonergic psychedelics are not significantly dopaminergic, and 1cP-LSD is therefore assumed to be atypical in this regard. Any agonist activity at the D<sub>2</sub> receptor may contribute to its psychoactive effects in humans.<ref>{{cite journal | vauthors=((Marona-Lewicka, D.)), ((Thisted, R. A.)), ((Nichols, D. E.)) | journal=Psychopharmacology | title=Distinct temporal phases in the behavioral pharmacology of LSD: dopamine D2 receptor-mediated effects in the rat and implications for psychosis | volume=180 | issue=3 | pages=427–435 | date= July 2005 | issn=0033-3158 | doi=10.1007/s00213-005-2183-9}}</ref> Additionally, 1cP-LSD likely binds to most serotonin receptor subtypes except for the 5-HT<sub>3</sub> and 5-HT<sub>4</sub> receptors. However, most of these receptors are affected at too low affinity to be sufficiently activated by the brain concentration of approximately 10–20 nM.<ref name="Nichols2004">{{cite journal | vauthors=((Nichols, D. E.)) | journal=Pharmacology & Therapeutics | title=Hallucinogens | volume=101 | issue=2 | pages=131–181 | date= February 2004 | url=https://linkinghub.elsevier.com/retrieve/pii/S0163725803001657 | issn=01637258 | doi=10.1016/j.pharmthera.2003.11.002}}</ref> Recreational doses likely can affect 5-HT<sub>1A</sub>, 5-HT<sub>2A</sub>, 5-HT<sub>2B</sub>, 5-HT<sub>2C</sub>, 5-HT<sub>5A</sub> [in cloned rat tissues]), and 5-HT<sub>6</sub> receptors.


1cP-LSD is likely to be a biased agonist that induces a conformation in serotonin receptors that preferentially recruits β-arrestin over activating G proteins.<ref>Chen Q, Tesmer JJ (January 2017). "A Receptor on Acid". ''Cell''. '''168''' (3): 339–341. doi:10.1016/j.cell.2017.01.012. PMC 5520807. <nowiki>PMID 28129534</nowiki>.</ref> A crystal structure of 5-HT<sub>2B</sub> bound to 1cP-LSD reveals an extracellular loop that forms a lid over the diethylamide end of the binding cavity which explains the slow rate of unbinding from serotonin receptors.<ref>UNC Health Care (January 26, 2017). "This is LSD Attached to a Brain Cell Serotonin Receptor (Update)". ''Phys.org''.</ref>
1cP-LSD is likely to be a biased agonist that induces a conformation in serotonin receptors that preferentially recruits β-arrestin over activating G proteins.<ref>{{cite journal | vauthors=((Chen, Q.)), ((Tesmer, J. J. G.)) | journal=Cell | title=A Receptor on Acid | volume=168 | issue=3 | pages=339–341 | date= January 2017 | url=https://linkinghub.elsevier.com/retrieve/pii/S0092867417300600 | issn=00928674 | doi=10.1016/j.cell.2017.01.012}}</ref> A crystal structure of 5-HT<sub>2B</sub> bound to 1cP-LSD reveals an extracellular loop that forms a lid over the diethylamide end of the binding cavity which explains the slow rate of unbinding from serotonin receptors.<ref>{{Citation | vauthors=((University of North Carolina Health Care)) | year=2017 | title=This is LSD attached to a brain cell serotonin receptor (Update) | url=https://phys.org/news/2017-01-lsd-brain-cell-serotonin-receptor.html}}</ref>


==Subjective effects==
==Subjective effects==
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*'''[[Effect::Memory suppression]]'''
*'''[[Effect::Memory suppression]]'''
**'''[[Effect::Ego death]]'''
**'''[[Effect::Ego death]]'''
*'''[[Effect::Ego replacement]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought disorganization]]'''
*'''[[Effect::Thought disorganization]]'''
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*'''[[Effect::Time distortion]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Addiction suppression]]'''


}}
}}
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*'''[[Cannabis]]''' - Cannabis strongly intensifies the sensory and cognitive effects of 1cP-LSD. Extreme caution is advised when using this combination as it can significantly increase the chances of a negative psychological reaction like [[anxiety]], [[confusion]] and [[psychosis]]. Users are advised to start off with only a fraction of their usual cannabis dose and take long breaks between hits to avoid over intake.
*'''[[Cannabis]]''' - Cannabis strongly intensifies the sensory and cognitive effects of 1cP-LSD. Extreme caution is advised when using this combination as it can significantly increase the chances of a negative psychological reaction like [[anxiety]], [[confusion]] and [[psychosis]]. Users are advised to start off with only a fraction of their usual cannabis dose and take long breaks between hits to avoid over intake.
*'''[[Dissociatives]]''' - 1cP-LSD enhances the cognitive, visual and general hallucinatory effects of dissociatives. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] and [[internal hallucinations]] become more vivid and intense on 1cP-LSD. These effects correspond with an increased risk of [[confusion]], [[delusions]], and [[psychosis]].
*'''[[Dissociatives]]''' - 1cP-LSD enhances the cognitive, visual and general hallucinatory effects of dissociatives. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] and [[internal hallucinations]] become more vivid and intense on 1cP-LSD. These effects correspond with an increased risk of [[confusion]], [[delusions]], and [[psychosis]].
*'''[[MDMA]]''' - 1cP-LSD and MDMA are highly synergistic and mutually enhance each other's physical, cognitive, and visual effects. The synergy between these substances is unpredictable, and it is advised to start with markedly lower doses than one would take for each individually. There is some evidence that suggests LSD increases the neurotoxicity of MDMA, which may be relevant to 1cP-LSD as well.<ref>Armstrong, B. D., Paik, E., Chhith, S., Lelievre, V., Waschek, J. A., & Howard, S. G. (2004). Potentiation of (DL)‐3, 4‐methylenedioxymethamphetamine (MDMA)‐induced toxicity by the serotonin 2A receptor partial agonist d‐lysergic acid diethylamide (LSD), and the protection of same by the serotonin 2A/2C receptor antagonist MDL 11,939. Neuroscience Research Communications, 35(2), 83-95. https://doi.org/10.1002/nrc.20023</ref><ref>Potentiation of MDMA-induced dopamine release and serotonin neurotoxicity by 5-HT2 receptor agonists | https://indiana.pure.elsevier.com/en/publications/potentiation-of-34-methylenedioxymethamphetamine-induced-dopamine</ref><ref>Ecstasy induces apoptosis via 5-HT(2A)-receptor stimulation in cortical neurons. | https://www.ncbi.nlm.nih.gov/pubmed/17572501</ref>
*'''[[MDMA]]''' - 1cP-LSD and MDMA are highly synergistic and mutually enhance each other's physical, cognitive, and visual effects. The synergy between these substances is unpredictable, and it is advised to start with markedly lower doses than one would take for each individually. There is some evidence that suggests LSD increases the neurotoxicity of MDMA, which may be relevant to 1cP-LSD as well.<ref>{{cite journal | vauthors=((Armstrong, B. D.)), ((Paik, E.)), ((Chhith, S.)), ((Lelievre, V.)), ((Waschek, J. A.)), ((Howard, S. G.)) | journal=Neuroscience Research Communications | title=Potentiation of (DL)-3,4-methylenedioxymethamphetamine (MDMA)-induced toxicity by the serotonin 2A receptior partial agonist d-lysergic acid diethylamide (LSD), and the protection of same by the serotonin 2A/2C receptor antagonist MDL 11,939 | volume=35 | issue=2 | pages=83–95 | date= September 2004 | url=https://onlinelibrary.wiley.com/doi/10.1002/nrc.20023 | issn=0893-6609 | doi=10.1002/nrc.20023}}</ref><ref>{{cite journal | vauthors=((Gudelsky, G. A.)), ((Yamamoto, B. K.)), ((Frank Nash, J.)) | journal=European Journal of Pharmacology | title=Potentiation of 3,4-methylenedioxymethamphetamine-induced dopamine release and serotonin neurotoxicity by 5-HT2 receptor agonists | volume=264 | issue=3 | pages=325–330 | date= November 1994 | url=https://linkinghub.elsevier.com/retrieve/pii/0014299994906696 | issn=00142999 | doi=10.1016/0014-2999(94)90669-6}}</ref><ref>{{cite journal | vauthors=((Capela, J. P.)), ((Fernandes, E.)), ((Remião, F.)), ((Bastos, M. L.)), ((Meisel, A.)), ((Carvalho, F.)) | journal=Neurotoxicology | title=Ecstasy induces apoptosis via 5-HT(2A)-receptor stimulation in cortical neurons | volume=28 | issue=4 | pages=868–875 | date= July 2007 | issn=0161-813X | doi=10.1016/j.neuro.2007.04.005}}</ref>


===Experience reports===
===Experience reports===
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===Dependence and abuse potential===
===Dependence and abuse potential===
Although no formal studies have been conducted, it is assumed that like LSD itself, 1cP-LSD is [[Addiction potential::non-addictive with a low abuse potential]]. There are no literature reports of successful attempts to train animals to self-administer LSD — an animal model predictive of abuse liability — indicating that it does not have the necessary pharmacology to either initiate or maintain dependence.<ref>{{cite journal|last1=Nichols|first1=David E.|author-link=David E. Nichols|year=2004|title=Hallucinogens|journal=Pharmacology & Therapeutics|volume=101|issue=2|pages=131-181|doi=10.1016/j.pharmthera.2003.11.002|issn=0163-7258}}</ref> Likewise, there is virtually no withdrawal syndrome when chronic use of LSD is stopped.{{citation needed}} It is likely that 1cP-LSD does not deviate from LSD in this respect.
Although no formal studies have been conducted, it is assumed that like LSD itself, 1cP-LSD is [[Addiction potential::non-addictive with a low abuse potential]]. There are no literature reports of successful attempts to train animals to self-administer LSD — an animal model predictive of abuse liability — indicating that it does not have the necessary pharmacology to either initiate or maintain dependence.<ref name="Nichols2004" /> Likewise, there is virtually no withdrawal syndrome when chronic use of LSD is stopped.{{citation needed}} It is likely that 1cP-LSD does not deviate from LSD in this respect.


Tolerance to the effects of 1cP-LSD is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::5-7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::14 days]] to be back at baseline (in the absence of further consumption). 1cP-LSD produces cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the use of 1cP-LSD they will have a reduced effect.
Tolerance to the effects of 1cP-LSD is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::5-7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::14 days]] to be back at baseline (in the absence of further consumption). 1cP-LSD produces cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the use of 1cP-LSD they will have a reduced effect.
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{{LegalStub}}
{{LegalStub}}


*'''Canada''': 1cP- LSD is unscheduled in Canada.
*'''Czech Republic''': 1cP-LSD is not a controlled substance, and is not named on the list of illegal substances.<ref>{{cite web | url=https://www.zakonyprolidi.cz/cs/2013-463 | title=Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek | publisher=Zákony pro lidi | language=Czech|id=178/2013|date=December 18, 2013}}</ref>
*'''Germany''': 1cP-LSD is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=September 16, 2021|language=de}}</ref> as of July 2, 2021.<ref>{{Cite web|access-date=September 16, 2021|language=de|pages=2231–2243|publication-date=July 2, 2021|publisher=Bundesanzeiger Verlag|title=Zweite Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl121s2231.pdf|work=Bundesgesetzblatt Jahrgang 2021 Teil I Nr. 38}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=September 16, 2021|language=de}}</ref>
*'''Germany''': 1cP-LSD is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=September 16, 2021|language=de}}</ref> as of July 2, 2021.<ref>{{Cite web|access-date=September 16, 2021|language=de|pages=2231–2243|publication-date=July 2, 2021|publisher=Bundesanzeiger Verlag|title=Zweite Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl121s2231.pdf|work=Bundesgesetzblatt Jahrgang 2021 Teil I Nr. 38}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=September 16, 2021|language=de}}</ref>
*'''Japan''': 1cP-LSD is controlled by the Pharmaceutical Affairs Law in Japan, making it illegal to possess or sell.<ref>{{cite web|title=指定薬物を指定する省令が公布されました|language=ja|url=https://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/oshirase/20210122-1.html|publisher=厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]|access-date=March 25, 2021}}</ref>
*'''Japan''': 1cP-LSD is controlled by the Pharmaceutical Affairs Law in Japan, making it illegal to possess or sell.<ref>{{cite web|title=指定薬物を指定する省令が公布されました|language=ja|url=https://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/oshirase/20210122-1.html|publisher=厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]|access-date=March 25, 2021}}</ref>
*'''Sweden''': Sweden's public health agency suggested classifying 1cP-LSD as a dangerous substance on December 18, 2019.<ref>{{cite web|url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/december/tjugotre-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/|title=Tjugotre ämnen föreslås klassas som narkotika eller hälsofarlig vara | trans-title = Twenty-three substances are proposed to be classified as drugs or dangerous goods |publisher=Folkhälsomyndigheten [Public Health Agency of Sweden]|language=sv|date=December 18, 2019|access-date=July 14, 2020}}</ref>
*'''Sweden''': Sweden's public health agency suggested classifying 1cP-LSD as a dangerous substance on December 18, 2019.<ref>{{cite web|url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/december/tjugotre-amnen-foreslas-klassas-som-narkotika-eller-halsofarlig-vara/|title=Tjugotre ämnen föreslås klassas som narkotika eller hälsofarlig vara | trans-title = Twenty-three substances are proposed to be classified as drugs or dangerous goods |publisher=Folkhälsomyndigheten [Public Health Agency of Sweden]|language=sv|date=December 18, 2019|access-date=July 14, 2020}}</ref>
*'''Turkey:''' 1cP-LSD is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="25 mart 2020, Cumhurbaşkanı Kararı CK Karar Sayısı : 2307">https://mevzuat.gov.tr/MevzuatMetin/20.5.2307.pdf</ref>
*'''Turkey:''' 1cP-LSD is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="25 mart 2020, Cumhurbaşkanı Kararı CK Karar Sayısı : 2307">{{Citation | vauthors=((ERDOĞAN, R. T.)) | year=2020 | title=CUMHURBAŞKANI KARARI | publisher=Resmî Gazete | url=https://mevzuat.gov.tr/MevzuatMetin/20.5.2307.pdf}}</ref>
*'''United Kingdom''': 1cP-LSD is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26, 2016.<ref>{{cite web|title=Psychoactive Substances Act 2016|publisher=legislation.gov.uk|url=http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted|access-date=July 14, 2020}}</ref>
*'''United Kingdom''': 1cP-LSD is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26, 2016.<ref>{{cite web|title=Psychoactive Substances Act 2016|publisher=legislation.gov.uk|url=http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted|access-date=July 14, 2020}}</ref>


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*[[LSD]]
*[[LSD]]
*[[1P-LSD]]
*[[1P-LSD]]
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==External links==
==External links==
(List along order below)
 
* [https://en.wikipedia.org/wiki/SUBSTANCE SUBSTANCE (Wikipedia)]
*[https://en.wikipedia.org/wiki/1cP-LSD 1cP-LSD (Wikipedia)]
* SUBSTANCE (Erowid Vault)
*[https://isomerdesign.com/PiHKAL/explore.php?id=7484 1-CPA-LSD (Isomer Design)]
* SUBSTANCE ([''PiHKAL'' or ''TiHKAL''] / Isomer Design)


==Literature==
==Literature==
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*APA formatted reference


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