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1cP-LSD: Difference between revisions
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'''1-Cyclopropionyl-''d''-lysergic acid diethylamide''' (also known as '''1cP-LSD''') is a lesser-known novel [[Psychoactive class::psychedelic]] substance of the [[Chemical class::lysergamide]] class. It is chemically similar to [[LSD]] and other LSD analogs like [[1B-LSD]], [[ALD-52]], and [[1P-LSD]]. | '''1-Cyclopropionyl-''d''-lysergic acid diethylamide''' (also known as '''1cP-LSD''') is a lesser-known novel [[Psychoactive class::psychedelic]] substance of the [[Chemical class::lysergamide]] class. It is chemically similar to [[LSD]] and other LSD analogs like [[1B-LSD]], [[ALD-52]], and [[1P-LSD]]. It is suspected to produce its effects by binding to [[serotonin]] [[receptors]] in the brain; however, its precise mechanism is not known.<ref name="Brandt2020">{{cite journal|title=Return of the lysergamides. Part VI: Analytical and behavioural characterization of 1‐cyclopropanoyl‐d‐lysergic acid diethylamide (1CP‐LSD)|first1=Simon D.|last1=Brandt|first2=Pierce V.|last2=Kavanagh|first3=Folker|last3=Westphal|first4=Alexander|last4=Stratford|first5=Anna U.|last5=Odland|first6=Adam K.|last6=Klein|first7=Geraldine|last7=Dowling|first8=Nicola M.|last8=Dempster|first9=Jason|last9=Wallach|first10=Torsten|last10=Passie|first11=Adam L.|last11=Halberstadt|date=March 16, 2020|doi=10.1002/dta.2789|volume=12|issue=6|journal=Drug Testing and Analysis|pages=812-826|eissn=1942-7611|issn=1942-7603|oclc=231680670|pmid=32180350}}</ref> | ||
The origins of 1cP-LSD are not well-documented. Following 1P-LSD's prohibition in Germany, 1cP-LSD appeared on the online [[research chemical]] market in 2019.{{citation needed}} Like other LSD analogs, it was marketed as a legal alternative to LSD and 1P-LSD. | The origins of 1cP-LSD are not well-documented. Following 1P-LSD's prohibition in Germany, 1cP-LSD appeared on the online [[research chemical]] market in 2019.{{citation needed}} Like other LSD analogs, it was marketed as a legal alternative to LSD and 1P-LSD. | ||
[[Subjective effects]] include [[geometry|open and closed eye visuals]], [[time distortion]], [[conceptual thinking]], [[introspection|enhanced introspection]], [[euphoria]], and [[ego loss]]. A study found that incubation of 1cP‐LSD with human serum led to the formation of LSD, indicating that it may act as a [[prodrug]] for LSD.<ref name="Brandt2020"></ref> Anecdotal reports appear to be consistent with this theory, with most users reporting near-identical effects as LSD. It has a longer and | [[Subjective effects]] include [[geometry|open and closed eye visuals]], [[time distortion]], [[conceptual thinking]], [[introspection|enhanced introspection]], [[euphoria]], and [[ego loss]]. A study found that incubation of 1cP‐LSD with human serum led to the formation of LSD, indicating that it may act as a [[prodrug]] for LSD.<ref name="Brandt2020"></ref> Anecdotal reports appear to be consistent with this theory, with most users reporting near-identical effects as LSD. It has been reported to have a moderately longer and subtler come up, along with mildly smoother cognitive and physical effects compared to 1P-LSD. | ||
Limited data exist on the pharmacology, metabolism, and toxicity of 1cP-LSD. While it is presumed to have a [[LSD#Toxicity and harm potential|similar risk profile as LSD]] and its analogs, which are generally thought to be safe in controlled settings, | Limited data exist on the pharmacology, metabolism, and toxicity of 1cP-LSD. While it is presumed to have a [[LSD#Toxicity and harm potential|similar risk profile as LSD]] and its analogs, which are generally thought to be safe in controlled settings, reliable scientific data is lacking. It is highly advised to use [[harm reduction practices]] if using this substance. | ||
==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> | |||
1cP-LSD | |||
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}} | |||
==Chemistry== | ==Chemistry== | ||
1cP-LSD is a semisynthetic compound of the [[lysergamide]] family. It is similar to [[LSD]] and is named for the cyclopropionyl group bound to the nitrogen of the polycyclic indole group of LSD. The cyclopropionyl group consists of a carbonyl ring with the chemical formula C<sub>3</sub>H<sub>6</sub> bound to an amino group. | 1cP-LSD is a semisynthetic compound of the [[lysergamide]] family. It is similar to [[LSD]] and is named for the cyclopropionyl group bound to the nitrogen of the polycyclic indole group of LSD. The cyclopropionyl group consists of a carbonyl ring with the chemical formula C<sub>3</sub>H<sub>6</sub> bound to an amino group. | ||
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. | ||
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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. | |||
1cP-LSD is 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>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> | ||
==Subjective effects== | ==Subjective effects== | ||