LAMPA

LAMPA
Clinical data
Other names	LMP
Legal status
Legal status	US: Unscheduled;
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;

LAMPA (N-methyl-N-propyl lysergamide) 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]

References

^ Abramson HA, Rolo A (1967). "Comparison of LSD with methysergide and psilocybin on test subjects." (PDF). In Abramson HA (ed.). The use of LSD in psychotherapy and alcoholism. Bobbs-Merrill Company Inc. pp. 53–57. Retrieved 15 May 2022.
^ Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, et al. (February 2019). "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology. 236 (2): 799–808. doi:10.1007/s00213-018-5055-9. PMC 6848745. PMID 30298278.
^ Pottie E, Glatfelter GC, Baumann MH, Stove CP (2024). "Differential in Vitro Activation Profiles for Psychedelic versus Non-psychedelic Ergolines at the 5-HT2A Receptor". Emerging Trends in Drugs, Addictions, and Health. 4: 100109. doi:10.1016/j.etdah.2023.100109.

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[1] Abramson HA, Rolo A (1967). "Comparison of LSD with methysergide and psilocybin on test subjects." (PDF). In Abramson HA (ed.). The use of LSD in psychotherapy and alcoholism. Bobbs-Merrill Company Inc. pp. 53–57. Retrieved 15 May 2022.

[2] Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, et al. (February 2019). "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology. 236 (2): 799–808. doi:10.1007/s00213-018-5055-9. PMC 6848745. PMID 30298278.

[PottieGlatfelterBaumann2024-3] Pottie E, Glatfelter GC, Baumann MH, Stove CP (2024). "Differential in Vitro Activation Profiles for Psychedelic versus Non-psychedelic Ergolines at the 5-HT2A Receptor". Emerging Trends in Drugs, Addictions, and Health. 4: 100109. doi:10.1016/j.etdah.2023.100109.

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v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromerguride (2-bromolisuride) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mergocriptine Mesulergine Metergoline Metergotamine MIPLA Methysergide Propisergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD (lysergide) LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine Brazergoline Cianergoline CY-208,243 Delergotrile Descarboxylysergic acid Disulergine Dosergoside Ergoline Etisulergine Lergotrile Nicergoline Pergolide Proterguride Romergoline Terguride Tiomergine Voxergolide
Related compounds	Adrogolide Naxagolide Quinagolide
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

See also

References