LAMPA

Lysergic acid methylpropylamide (LAMPA, LAMP, or LMP), also known as LMP-55 or as N-methyl-N-propyllysergamide, is a structural analogue of lysergic acid diethylamide (LSD) that has been studied as a potential treatment for alcoholism.^[1] In animal studies, LAMPA was found to be nearly equipotent to ECPLA and MIPLA for inducing a head-twitch response. LAMPA appears to be significantly less potent than LSD in humans, producing little to no noticeable effects at doses of 100 μg.^[2] It shows reduced-efficacy partial agonism of the serotonin 5-HT_2A receptor relative to LSD, which may be responsible for its equivocal hallucinogenic effects.^[3]

LAMPA

Clinical data
Other names	Lysergic acid methylpropylamide; LMP; LAMP; LAMPA; LMP-55; LMP55; N-Methyl-N-propyllysergamide; N,6-Dimethyl-N-propyl-9,10-didehydroergoline-8β-carboxamide
Legal status
Legal status	US: Schedule I (isomer of LSD)
Identifiers
IUPAC name N,7-dimethyl-N-propyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number	40158-98-3
PubChem CID	613620
ChemSpider	533384
CompTox Dashboard (EPA)	DTXSID701043313
Chemical and physical data
Formula	C20H25N3O
Molar mass	323.440 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCN(C)C(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI InChI=InChI=1S/C20H25N3O/c1-4-8-22(2)20(24)14-9-16-15-6-5-7-17-19(15)13(11-21-17)10-18(16)23(3)12-14/h5-7,9,11,14,18,21H,4,8,10,12H2,1-3H3 Key:CZRJGQXHVRNZRZ-UHFFFAOYSA-N

See also

• Ethylcyclopropyllysergamide (ECPLA)
• Methylisopropyllysergamide (MIPLA)
• Ethylpropyllysergamide (EPLA)