Diallyllysergamide

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]

Diallyllysergamide

Clinical data
Other names	DAL; Lysergic acid diallylamide; LDA; d-Lysergic acid diallylamide; d-Diallyllysergamide
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	US: Analogue to a Schedule I/II drug (but only if it is intended for human consumption)
Identifiers
IUPAC name (6aR,9R)-N,N-Diallyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide
CAS Number	73032-97-0
PubChem CID	57481013
ChemSpider	21106294 Y
CompTox Dashboard (EPA)	DTXSID501046535
ECHA InfoCard	100.163.206
Chemical and physical data
Formula	C22H25N3O
Molar mass	347.462 g·mol−1
3D model (JSmol)	Interactive image
SMILES C=CCN(CC=C)C(=O)[C@@H]2C=C1c3cccc4[nH]cc(C[C@H]1N(C)C2)c34
InChI 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 Y Key:VAMQYGHNZLRSSA-OXQOHEQNSA-N Y
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Use and effects

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

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

Pharmacology

Pharmacodynamics

DAL interacts with serotonin receptors, including the serotonin 5-HT_1A, 5-HT_2A, and 5-HT_2C receptors.^[2] It acts as a serotonin 5-HT_2A receptor agonist, but with about 5-fold lower potency than LSD.^[2]

See also

• Substituted lysergamide
• Lysergic acid dimethylamide (DAM-57)
• Lysergic acid dipropylamide (DPL)
• Lysergic acid dibutylamide (LBB-66)
• Substituted tryptamine