Lysergic acid dipropylamide

Lysergic acid dipropylamide (LSDP), also known as N,N-dipropyllysergamide (DPL), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).^[1][2][3][4] It is the analogue of LSD in which the amide group has two propyl substitutions instead of two ethyl substituents.^{[1][2][3][5][6]}

LSDP

Clinical data
Other names	Lysergic acid dipropylamide; LSDP; LSDPr; LADP; N,N-Dipropyllysergamide; DPL
Routes of administration	Oral
Drug class	Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name (6aR,9R)-7-methyl-N,N-dipropyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID	129714166
Chemical and physical data
Formula	C22H29N3O
Molar mass	351.494 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCN(CCC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI InChI=1S/C22H29N3O/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/h6-8,11,13,16,20,23H,4-5,9-10,12,14H2,1-3H3/t16-,20-/m1/s1 Key:QKKQYCDPPPJVQI-OXQOHEQNSA-N

The drug has about 10% or less of the potency of LSD as a psychedelic and its dose is greater than 1 mg orally.^{[7][8][9][4][10]} It has been reported however that, in contrast to LSD, LSDP produces LSD-like autonomic effects at much lower doses (<1 mg) than those at which its psychedelic effects occur.^[8][4][10] The drug was initially thought to be non-hallucinogenic after only being tested at sub-milligram doses.^[8][10]

LSDP was first described in the literature by Albert Hofmann and colleagues by 1955.^[11][10][4] Unlike various other LSD analogues, it was never given a specific code name (as in e.g. "LSD-25").^[12] Its psychedelic effects were also reported by Hofmann.^[4]

See also

• Substituted lysergamide
• Lysergic acid methylpropylamide (LAMPA)
• Lysergic acid dimethylamide (DAM-57)
• Lysergic acid diallylamide (DAL)
• Ethylpropyllysergamide (EPLA)
• PRO-LAD (6-propyl-6-nor-LSD)