LA-Azepane

LA-Azepane
Clinical data
Other namesLSD-Azepane; Lysergic acid azepane; Lysergic acid hexamethylene imide; N-(Azepan-1-yl)lysergamide
ATC code
  • None
Identifiers
  • (Azepan-1-yl)[(6aS,9R)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl]methanone
Chemical and physical data
FormulaC22H27N3O
Molar mass349.478 g·mol−1
3D model (JSmol)
  • CN1C[C@@H](C=C2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N1CCCCCC1
  • InChI=1S/C22H27N3O/c1-24-14-16(22(26)25-9-4-2-3-5-10-25)11-18-17-7-6-8-19-21(17)15(13-23-19)12-20(18)24/h6-8,11,13,16,20,23H,2-5,9-10,12,14H2,1H3/t16-,20-/m1/s1
  • Key:WBZXJLBFYQVYOH-OXQOHEQNSA-N

LA-Azepane, or LSD-Azepane, also known as lysergic acid azepane or as lysergic acid hexamethylene imide, is a chemical compound of the lysergamide family related to lysergic acid diethylamide (LSD).[1] It is an derivative of LSD in which the N,N-diethylamide moiety has been cyclized to form an azepane ring.[1] The compound is very little studied and described itself, but is closely related to other amide-cyclized LSD analogues including LA-Pip, LSM-775 (LA-Morph), LPD-824 (LA-Pyr), LPN, LSZ (LA-Azetidide), and LA-Aziridine, among others.[2][3] The chemical synthesis of the compound has been described.[1] LA-Azepane was first described in the literature in a patent by Richard P. Pioch at Eli Lilly and Company in 1961.[1] The patent had been filed 5 years previously in 1956.[1]

See also

References

  1. ^ a b c d e US 2997470, Pioch RP, "Lysergic acid amides", issued 22 August 1961, assigned to Eli Lilly and Company  EXAMPLE 38 Preparation of d-lysergic acid hexamethylene imide: [...]
  2. ^ Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524. Table 1 5-HT2A 5-HT2C, and 5-HT1A receptor affinity and functional effects for selected lysergamides [...]
  3. ^ Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X.
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