1V-LSD

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

1V-LSD
Clinical data
Routes of
administration		oral
Legal status
Legal status
Identifiers
IUPAC name
  • (6aR,9R)-N,N-Diethyl-7-methyl-4-propanoyl-4,,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
PubChem CID
UNII
Chemical and physical data
FormulaC25H33N3O2
Molar mass407.558 g·mol−1
3D model (JSmol)
SMILES
  • CCN(CC)C(=O)[C@@H]5C=C2[C@@H](Cc3cn(C(=O)CCCC)c4cccc2c34)N(C)C5
InChI
  • 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

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.[2]

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.[4]

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

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.[9]

An amendment to the NpSG banned the sale of 1V-LSD in Germany in September 2022.

1v-LSD strip blotters

See also

References
  1. "1V-LSD (solution)". www.caymanchem.com.
  2. 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: dta.3205. doi:10.1002/dta.3205. PMID 34837347.
  3. "1V-LSD - legales LSD 3.0" (in German).
  4. 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. PMID 31756337.
  5. 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.
  6. 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.
  7. "REACTIONS 1V-LSD".
  8. "1V-LSD reaction with the ehrlich reagent".
  9. Kim Chan-hyuk, Regulator names 1V-LSD as narcotic drug temporarily. Korea Biomedical Review, 5 July 2022


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