1V-LSD
1V-LSD Chemical Structure.svg
Clinical data
Routes of
administration
oral
Legal status
Legal status
  • DE: legal
  • EU: legal
Identifiers
  • (6aR,9R)-N,N-Diethyl-7-methyl-4-propanoyl-4,,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
UNII
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 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 since a recent amendment to the German NpSG was enforced which controls 1P-LSD and now 1cP-LSD and several other lysergamides.[3]

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]

Legal position

Since 1V-LSD is relatively new to the market, it is still uncontrolled in most countries. Specifically, 1V-LSD is not controlled in Germany since it does not fulfil all the requirements for legislation under section 5.2 of the NpSG. The substance has neither been recorded in the German BtMG.[9]

Since March 2nd 2022, 1V-LSD has been under investigation in Sweden and may therefore soon become controlled.

1v-LSD strip blotters
1v-LSD strip blotters

See also

References

  1. ^ "1V-LSD (solution)". www.caymanchem.com.
  2. ^ 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: 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. ^ "Zweite Verordnung zur Änderung der Anlage desNeue-psychoaktive-Stoffe-Gesetzes" [Second ordinance amending the annex to the New Psychoactive Substances Act] (PDF). Regulation of the Federal Ministry of Health (in German). 12 May 2021.