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Diallyllysergamide

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Diallyllysergamide
Clinical data
Other namesDAL; Lysergic acid diallylamide; LDA; d-Lysergic acid diallylamide; d-Diallyllysergamide
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Identifiers
  • (6aR,9R)-N,N-Diallyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.163.206 Edit this at Wikidata
Chemical and physical data
FormulaC22H25N3O
Molar mass347.462 g·mol−1
3D model (JSmol)
  • C=CCN(CC=C)C(=O)[C@@H]2C=C1c3cccc4[nH]cc(C[C@H]1N(C)C2)c34
  • InChI=1S/C22H25N3O/c1-4-9-25(10-5-2)22(26)16-11-18-17-7-6-8-19-21(17)15(13-23-19)12-20(18)24(3)14-16/h4-8,11,13,16,20,23H,1-2,9-10,12,14H2,3H3/t16-,20-/m1/s1 checkY
  • Key:VAMQYGHNZLRSSA-OXQOHEQNSA-N checkY
  (verify)

N,N-Diallyllysergamide (DAL), also known as lysergic acid diallylamide (LDA), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).[1][2] It is taken orally.[1]

Use and effects

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In his 1997 book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin described DAL as producing "at best a touch of sparkle" of LSD at dose of 600 μg of the tartrate salt taken orally, but as also producing a sedation.[1] Subsequently, in a 2003 literature review, Shulgin listed an active dose as greater than 1 mg.[3] He has described the drug as being at least an order of magnitude less potent than LSD.[1][3]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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DAL interacts with serotonin receptors, including the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors.[2] It acts as a serotonin 5-HT2A receptor agonist, but with about 5-fold lower potency than LSD.[2]

See also

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References

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  1. ^ a b c d e Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "DAL, N,N-Diallyllysergamide. As the tartrate salt, there is at best a touch of sparkle seen at 600 micrograms orally, but there is a sedation also reported. It is certainly an order of magnitude less potent than LSD itself."
  2. ^ a b c Nichols DE (2018). Halberstadt AL, Vollenweider FX, Nichols DE (eds.). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. Springer. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
  3. ^ a b Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.
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