1V-LSD

Last updated

1V-LSD
1V-LSD Chemical Structure.svg
Clinical data
Other names1-Valeryl-LSD; 1-Valeroyl-LSD; 1-Pentanoyl-LSD; Valerie; 1-Valeryl-N,N-diethyllysergamide
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
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C25H33N3O2
Molar mass 407.558 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, also known as 1-valeryl-LSD or by the nickname Valerie, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). [1] [2] It is an analogue of LSD and is thought to act as a prodrug of LSD. [3]

Contents

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]

Interactions

Pharmacology

Pharmacodynamics

As demonstrated with other N-acylated derivatives of LSD, 1V-LSD is believed to serve as a prodrug for LSD but may also act directly as a weak partial agonist at the serotonin 5-HT2A receptor. [3]

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

Synthesis

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]

Detection

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]

Analogues

Related compounds include 1B-LSD, 1cP-LSD, 1D-LSD, 1P-LSD, and AL-LAD, among others.

Society and culture

1v-LSD strip blotters. 1v-LSD strip blotters.jpg
1v-LSD strip blotters.

Germany

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

North America

1V-LSD is not a controlled substance in North America (United States and Canada), unless sold for human consumption in the US. [11]

South Korea

1V-LSD was placed under legal control in South Korea in July 2022 on a temporary but renewable basis. [12]

Sweden

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

See also

References

  1. ↑ "1V-LSD (solution)". www.caymanchem.com.
  2. ↑ "1V-LSD PsychonautWiki". Psychonautwiki.
  3. 1 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. 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". PRO Test. 16 July 2021.
  9. ↑ "1V-LSD reaction with the ehrlich reagent". PRO Test. 16 July 2021.
  10. ↑ "Gesetzespanne: Gefährliche LSD-Derivate plötzlich legal".
  11. ↑ 21 U.S. Code § 813 - Treatment of controlled substance analogues
  12. ↑ Kim Chan-hyuk, Regulator names 1V-LSD as narcotic drug temporarily. Korea Biomedical Review, 5 July 2022
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