1V-LSD
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| IUPAC_name = (6aR,9R)-N,N-Diethyl-7-methyl-4-pentanoyl-4,,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
| image = 1V-LSD_Chemical_Structure.svg
| tradename =
| legal_AU = S8
| legal_CA = Unscheduled
| legal_DE = NpSG
| legal_UK = PSA
| legal_US = Unscheduled (when wasn't sold for human consumption)
| legal_UN = Unscheduled
| routes_of_administration = oral
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref =
| CAS_number = 3028950-70-8
| ATC_prefix =
| ATC_suffix =
| PubChem = 162368540
| ChemSpiderID =
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = V9TJ3HT283
| C = 25
| H = 33
| N = 3
| O = 2
| melting_point =
| smiles = CCN(CC)C(=O)[C@@H]5C=C2[C@@H](Cc3cn(C(=O)CCCC)c4cccc2c34)N(C)C5
| StdInChI = 1S/C25H33N3O2/c1-5-8-12-23(29)28-16-17-14-22-20(19-10-9-11-21(28)24(17)19)13-18(15-26(22)4)25(30)27(6-2)7-3/h9-11,13,16,18,22H,5-8,12,14-15H2,1-4H3/t18-,22-/m1/s1
| StdInChIKey = GIIBVGJWUZNECE-XMSQKQJNSA-N
| drug_name =
| alt =
| caption =
| type =
| MedlinePlus =
| licence_EU =
| licence_US =
| DrugBank =
}}
1V-LSD (1-valeryl-D-lysergic acid diethylamide), sometimes nicknamed Valerie, is a psychotropic substance and a research chemical with psychedelic effects.{{cite web |title=1V-LSD (solution) |url=https://www.caymanchem.com/product/35744/1v-lsd-(solution) |website=www.caymanchem.com |language=en}}{{cite news |title=1V-LSD PsychonautWiki |url=https://psychonautwiki.org/wiki/1V-LSD |newspaper=Psychonautwiki |language=en}} 1V-LSD is an artificial derivative of natural lysergic acid, which occurs in ergot alkaloids, as well as being an analogue of LSD.{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Pulver B, Morton K, Stratford A, Dowling G, Halberstadt AL | display-authors = 6 | title = Return of the lysergamides. Part VII: Analytical and behavioural characterization of 1-valeroyl-d-lysergic acid diethylamide (1V-LSD) | journal = Drug Testing and Analysis | pages = 733–740 | date = November 2021 | volume = 14 | issue = 4 | pmid = 34837347 | doi = 10.1002/dta.3205 | pmc = 9191648 }}
1V-LSD has been sold online until an amendment to the German NpSG was enforced in 2022 which controls 1P-LSD and now 1cP-LSD, 1V-LSD and several other lysergamides.{{cite web |title=1V-LSD - legales LSD 3.0 | website=YouTube | date=10 September 2021 |url=https://www.youtube.com/watch?v=EN6n6pUb7bs |language=de}}
Pharmacology
As demonstrated with other N-acylated derivatives of LSD, 1V-LSD is believed to serve as a prodrug for LSD but may also act as a weak partial agonist at the 5-HT2A receptor.
Animal studies
A Head-twitch response assay in mice found that 1V-LSD has a similar potency to 1P-LSD and 1cP-LSD, with behavioral effects also closely resembling these structural analogs.{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, McCorvy JD, Meyer MR, Wagmann L, Stratford A, Brandt SD | title = Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD) | journal = Neuropharmacology | volume = 172 | issue = | pages = 107856 | date = August 2020 | pmid = 31756337 | doi = 10.1016/j.neuropharm.2019.107856 | pmc = 9191647 | url = }}
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
Chemistry
1V-LSD is the condensation product of valeric acid (pentanoic acid) and LSD, where the valeroyl group is substituted on the NH position of the indole moiety.{{cite journal | vauthors = Umehara A, Ueda H, Tokuyama H | title = Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc2O | journal = The Journal of Organic Chemistry | volume = 81 | issue = 22 | pages = 11444–11453 | date = November 2016 | pmid = 27767302 | doi = 10.1021/acs.joc.6b02097 }}
Ehrlich's reagent is used to identify the presence of an indole moiety; the chemical backbone of the lysergamide and ergoline molecules.{{cite journal | vauthors = De Faubert Maunder MJ | title = A field test for hallucinogens: further improvements | journal = The Journal of Pharmacy and Pharmacology | volume = 26 | issue = 8 | pages = 637–8 | date = August 1974 | pmid = 4155730 | doi = 10.1111/j.2042-7158.1974.tb10677.x | s2cid = 97915487 }} However, as with other N-acylated lysergamides, 1V-LSD reacts very slowly to Ehrlich reagent and may not give reliable results if the reagent isn't fresh.{{cite web |title=REACTIONS 1V-LSD |date=16 July 2021 |url=https://www.protestkit.eu/1v-lsd-reagent-testing-results/ |language=en}}{{cite web |title=1V-LSD reaction with the ehrlich reagent |date=16 July 2021 |url=https://www.protestkit.eu/1v-lsd-reagent-testing-results/ |language=en}}
Legal position
1V-LSD is not a controlled substance in North America (United States and Canada), unless sold for human consumption in the US.{{Citation | title=21 U.S. Code § 813 - Treatment of controlled substance analogues | url=https://www.law.cornell.edu/uscode/text/21/813}}
Since March 2nd 2022, 1V-LSD has been under investigation in Sweden and may therefore soon become controlled.
1V-LSD was placed under legal control in South Korea in July 2022 on a temporary but renewable basis.[http://www.koreabiomed.com/news/articleView.html?idxno=14060 Kim Chan-hyuk, Regulator names 1V-LSD as narcotic drug temporarily. Korea Biomedical Review, 5 July 2022]
An amendment to the NpSG banned the sale of 1V-LSD in Germany in September 2022. Due to a interpunctation error in the actualised NpSG, the ban never took effect.{{cite web | url=https://www.lto.de/recht/hintergruende/h/lsd-derivate-drogen-legalisierung-strafbar-gesetztespanne-bmg-lauterbach-npsg-btmg/ | title=Gesetzespanne: Gefährliche LSD-Derivate plötzlich legal }} The law was amended in March 2023, now banning 1V-LSD.
See also
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/14087 1V-LSD - Isomer Design]
- [https://psychonautwiki.org/wiki/1V-LSD 1V-LSD - PsychonautWiki]
- [https://tripsitter.substack.com/p/1v-lsd Meet Valerie: LSD's Stealthy Sidekick (1V-LSD) - Tripsitter]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Ergolines}}