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LA-Azepane

From Wikipedia, the free encyclopedia

Pharmaceutical compound
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, orLSD-Azepane, also known aslysergic acid azepane or aslysergic acid hexamethylene imide, is achemical compound of thelysergamide family related tolysergic acid diethylamide (LSD).[1] It is anderivative of LSD in which theN,N-diethylamidemoiety has beencyclized to form anazepanering.[1] The compound is very little studied and described itself, but is closely related to other amide-cyclized LSDanalogues includingLA-Pip,LSM-775 (LA-Morph),LPD-824 (LA-Pyr),LPN,LSZ (LA-Azetidide), andLA-Aziridine, among others.[2][3] Thechemical synthesis of the compound has been described.[1] LA-Azepane was first described in the literature in apatent by Richard P. Pioch atEli Lilly and Company in 1961.[1] The patent had been filed 5 years previously in 1956.[1]

See also

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References

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  1. ^abcdeUS 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

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Ergolines
(incl.lysergines)
Clavines
(6,8-dimethylergolines)
Lysergamides
(lysergic acid amides)
Ergopeptines
(peptide ergolines)
Partial ergolines
Related compounds
Natural sources
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