Article · Wikipedia archive · Last revised Jul 1, 2026

LA-Azepane

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). It is an derivative of LSD in which the N,N-diethylamide moiety has been cyclized to form an azepane ring. 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. The chemical synthesis of the compound has been described. LA-Azepane was first described in the literature in a patent by Richard P. Pioch at Eli Lilly and Company in 1961. The patent had been filed 5 years previously in 1956.

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Jul 1, 2026
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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.23 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

See also

References

References

  1. 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.
External links