1P-LSD

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Structural formula
Structural formula of 1P-LSD
General
Surname 1P-LSD
other names
  • (6a R , 9 R ) -4-Propionyl- N , N -diethyl-7-methyl-4,6,6a, 7,8,9-hexahydroindolo [4,3- fg ] quinoline-9-carboxamide
  • 1-propionyl-d-lysergic acid diethylamide
Molecular formula C 23 H 29 N 3 O 2
External identifiers / databases
CAS number not forgiven
PubChem 119025985
Wikidata Q21096201
Drug information
Mechanism of action

partial agonist at serotonin (5-HT 2A ) receptors

properties
Molar mass 379.22 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1P-LSD (1-propionyl D -lysergsäurediethylamid) is a psychedelic acting psychotropic substance and research chemical . 1P-LSD is a derivative of lysergic acid , which in ergot alkaloids naturally occurring, as well as an analogue of LSD and an acyl - homologue of ALD-52 and 1B-LSD .

chemistry

1P-LSD blotter

Chemically, 1P-LSD belongs to the Ergoline structural class . The tetracyclic ergoline is characteristic of the chemical structure of ergot alkaloids . In contrast to LSD, 1P-LSD has an additional N 1 - propionyl group . Chemical modifications in the N 1 position are among the most frequently carried out changes to the ergoline system, since the indole nitrogen is easily accessible for alkylations , acylations , Mannich reactions and Michael additions .

  • Basic body of the Ergoline

  • Structural formula of LSD

  • Structural formula of ALD-52 (1-acetyl- D- LSD)

  • Structural formula of 1P-LSD (1-Propionyl- D -LSD)

  • Structural formula of 1B-LSD (1-butyryl- D -LSD)

pharmacology

It is assumed that 1P-LSD (like the homologues ALD-52 and 1B-LSD) is deacylated in the body with elimination of propionic acid to form LSD , since LSD-like symptoms have been found in animal models . An LC-MS analysis also shows that LSD is formed when 1P-LSD is incubated in human blood serum . It is therefore assumed that the effects profile is similar to that of ALD-52 and LSD. Recent research from 2019 supports the theory that 1P- LSD acts as a prodrug of LSD.

Legal position

As an ergoline derivative, 1P-LSD is subject to the New Psychoactive Substances Act (NpSG), which restricts, prohibits or punishes handling to certain cases (see § 3 , § 4 NpSG). It is illegal in Denmark, Germany, Sweden, Australia and Switzerland because of its structural similarity to LSD .

See also

Individual evidence

  1. ↑ a b Simon D. Brandt, Pierce V. Kavanagh, Folker Westphal, Alexander Stratford, Simon P. Elliott, Khoa Hoang, Jason Wallach, Adam L. Halberstadt: Return of the lysergamides. Part I: Analytical and behavioral characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD). In: Drug Testing and Analysis. 2015, pp. 891–902, doi : 10.1002 / dta.1884 .
  2. ^ A b F. Schifano, L. Orsolini, D. Papanti, J. Corkery: NPS: Medical Consequences Associated with Their Intake. In: Current topics in behavioral neurosciences. [Electronic publication before printing] June 2016, doi : 10.1007 / 7854_2016_15 , PMID 27272067 .
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ↑ Leigh D. Coney, Larissa J. Maier et al. a .: Genie in a blotter: A comparative study of LSD and LSD analogues' effects and user profile. In: Human Psychopharmacology: Clinical and Experimental. 32, 2017, p. E2599, doi : 10.1002 / hup.2599 .
  5. ↑ Petr Bulej, Ladislav Cvak: Chemical modifications of ergot alkaloids . In: Vladimir Kren, Ladislav Cvak (eds.): Ergot: The Genus Claviceps. Medicinal and Aromatic Plants - Industrial Profiles . CRC Press, 2004, ISBN 0203304195 , pp. 202-230.
  6. ↑ a b Lea Wagmann, Lilian HJ Richter a. a .: In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures. In: Analytical and Bioanalytical Chemistry. , doi : 10.1007 / s00216-018-1558-9 .
  7. ↑ Simon D. Brandt, Pierce V. Kavanagh et al. a .: Return of the lysergamides. Part III: Analytical characterization of N 6 -ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P-ETH-LAD). In: Drug Testing and Analysis. 2017, doi : 10.1002 / dta.2196 .
  8. ↑ AL Halberstadt, M. Chatha u. a .: Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD). In: Neuropharmacology. November 2019, doi : 10.1016 / j.neuropharm.2019.107856 , PMID 31756337 .
  9. ^ Uwe Hellmann : Commercial criminal law . Kohlhammer Verlag , October 30, 2018, ISBN 978-3-17-031444-3 , p. 250.