1V-LSD

1V-LSD
Clinical data
Routes of
administration		oral
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • CA: Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Under Psychoactive Substances Act
  • US: Unscheduled (when wasn't sold for human consumption)
  • UN: Unscheduled
Identifiers
  • (6aR,9R)-N,N-Diethyl-7-methyl-4-pentanoyl-4,,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H33N3O2
Molar mass407.558 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@@H]5C=C2[C@@H](Cc3cn(C(=O)CCCC)c4cccc2c34)N(C)C5
  • InChI=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
  • Key:GIIBVGJWUZNECE-XMSQKQJNSA-N

1V-LSD (1-valeryl-D-lysergic acid diethylamide), sometimes nicknamed Valerie, is a psychotropic substance and a research chemical with psychedelic effects.[1][2] 1V-LSD is an artificial derivative of natural lysergic acid, which occurs in ergot alkaloids, as well as being an analogue of LSD.[3] 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.[4]

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.[3]

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.[5]

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.[6] Ehrlich's reagent is used to identify the presence of an indole moiety; the chemical backbone of the lysergamide and ergoline molecules.[7] 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.[8][9]

1V-LSD is not a controlled substance in North America (United States and Canada), unless sold for human consumption in the US.[10]

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.[11]

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.[12] The law was amended in March 2023, now banning 1V-LSD.

1v-LSD strip blotters

See also

References

  1. ^ "1V-LSD (solution)". www.caymanchem.com.
  2. ^ "1V-LSD PsychonautWiki". Psychonautwiki.
  3. ^ a b Brandt SD, Kavanagh PV, Westphal F, Pulver B, Morton K, Stratford A, et al. (November 2021). "Return of the lysergamides. Part VII: Analytical and behavioural characterization of 1-valeroyl-d-lysergic acid diethylamide (1V-LSD)". Drug Testing and Analysis. 14 (4): 733–740. doi:10.1002/dta.3205. PMC 9191648. PMID 34837347.
  4. ^ "1V-LSD - legales LSD 3.0". YouTube (in German). 10 September 2021.
  5. ^ Halberstadt AL, Chatha M, Klein AK, McCorvy JD, Meyer MR, Wagmann L, Stratford A, Brandt SD (August 2020). "Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD)". Neuropharmacology. 172: 107856. doi:10.1016/j.neuropharm.2019.107856. PMC 9191647. PMID 31756337.
  6. ^ Umehara A, Ueda H, Tokuyama H (November 2016). "Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc2O". The Journal of Organic Chemistry. 81 (22): 11444–11453. doi:10.1021/acs.joc.6b02097. PMID 27767302.
  7. ^ De Faubert Maunder MJ (August 1974). "A field test for hallucinogens: further improvements". The Journal of Pharmacy and Pharmacology. 26 (8): 637–8. doi:10.1111/j.2042-7158.1974.tb10677.x. PMID 4155730. S2CID 97915487.
  8. ^ "REACTIONS 1V-LSD". 16 July 2021.
  9. ^ "1V-LSD reaction with the ehrlich reagent". 16 July 2021.
  10. ^ 21 U.S. Code § 813 - Treatment of controlled substance analogues
  11. ^ Kim Chan-hyuk, Regulator names 1V-LSD as narcotic drug temporarily. Korea Biomedical Review, 5 July 2022
  12. ^ "Gesetzespanne: Gefährliche LSD-Derivate plötzlich legal".


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