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Pharmaceutical compound
LME-54 Other names LME54; LME; Lysergic acid methylethylamide; LA-methylethylamide; N -Ethyl-N -methyllysergamide; N -Ethyl-N ,6-dimethyl-9,10-didehydroergoline-8β-carboxamide Routes of administration Oral [ 1] Drug class Serotonergic psychedelic ; Hallucinogen ATC code
(6aR ,9R )-N -ethyl-N ,7-dimethyl-6,6a ,8,9-tetrahydro-4H -indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID Formula C 19 H 23 N 3 O Molar mass 309.413 g·mol−1 3D model (JSmol )
CCN(C)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI=1S/C19H23N3O/c1-4-21(2)19(23)13-8-15-14-6-5-7-16-18(14)12(10-20-16)9-17(15)22(3)11-13/h5-8,10,13,17,20H,4,9,11H2,1-3H3/t13-,17-/m1/s1
Key:BROWGWCWLHAXPI-CXAGYDPISA-N
LME-54 , or simply LME , also known as lysergic acid methylethylamide or as N -methyl-N -ethyllysergamide , is a serotonergic psychedelic of the lysergamide family related to lysergic acid diethylamide (LSD; LSD-25).[ 2] [ 3] [ 4] [ 5] [ 1] It is the analogue of LSD in which one of the N -ethyl groups has been replaced with an N -methyl group .[ 2] [ 3] [ 4]
The drug was tested in humans at a dose of 25 μg and was found to produce no effects at this dose in several subjects and to produce weaker effects than a 25 μg dose of LSD in one subject.[ 1] Higher doses do not appear to have been assessed.[ 1] Based on these findings, LME-54 has been described as weakly active or active but less so than LSD with no specific numbers available.[ 2] [ 3] [ 4] [ 5] [ 6] [ 7] Its antiserotonergic activity in vitro does not appear to have been reported.[ 6]
LME-54 was first described in the scientific literature by Harold Alexander Abramson and Andre Rolo by 1965.[ 1] [ 8]
^ a b c d e Abramson HA, Rolo A (September 1965). "Lysergic acid diethylamide (LSD-25). 38. Comparison with action of methysergide and psilocybin on test subjects". The Journal of Asthma Research . 3 (1): 81– 96. doi :10.3109/02770906509106904 . PMID 5318626 .
^ a b c Shulgin AT (1976). "Psychotomimetic Agents" . In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse . Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59– 146. doi :10.1016/b978-0-12-290559-9.50011-9 . ISBN 978-0-12-290559-9 .
^ a b c Shulgin AT (1980). "Hallucinogens" . In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry . Vol. 3 (4 ed.). New York: Wiley. pp. 1109– 1137. ISBN 978-0-471-01572-7 . OCLC 219960627 .
^ a b c Shulgin AT (1982). "Chemistry of Psychotomimetics" . In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs . Handbook of Experimental Pharmacology. Vol. 55. Berlin: Springer Berlin Heidelberg. pp. 3– 29. doi :10.1007/978-3-642-67770-0_1 . ISBN 978-3-642-67772-4 . OCLC 8130916 .
^ 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 .
^ a b Oberlender RA (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens" . Purdue e-Pubs . Purdue University. Table 2. Relative potency values for lysergic acid amides. [...]
^ Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited" (PDF) . NIDA Research Monograph . 146 : 52– 73. PMID 8742794 . TABLE 2. Relative human potency of lysergic acid amides [...]
^ 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: The Second International Conference on the Use of LSD in Psychotherapy and Alcoholism, May 8th–May 10th, 1965 . Indianapolis: The Bobbs-Merill Company. pp. 53– 73. OCLC 302168 .
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs.
2,N ,N -TMT
4,N ,N -TMT
5-Bromo-DMT
5-Chloro-DMT
5-Fluoro-DMT
5-N ,N -TMT
7,N ,N -TMT
5-MeO-2,N ,N -TMT
5-MeO-4,N ,N -TMT
6-Fluoro-DMT
Bretisilocin (GM-2505; 5-fluoro-MET)
α-Alkyltryptamines
5-Methoxy-α-alkyltryptamines: 5-MeO-AET
α,N ,N -TMT (α-Me-DMT; Alpha-N)
5-MeO-AMT (α,O -DMS; Alpha-O)
α,N ,O -TMS (5-MeO-α,N -DMT)
α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT)
Others
Ergolines /lysergamides (e.g., LSD )
β-Carbolines and Harmala alkaloids (e.g., harmine , harmaline , 6-methoxyharmalan )
Iboga alkaloids (e.g., 18-MAC , 18-MC , coronaridine , ibogaine , ibogamine , ME-18-MC , noribogaine , tabernanthine , voacangine )
Ibogalogs (e.g., ibogainalog )
O -Methylnordehydrobufotenine
Partial ergolines (e.g., NDTDI , RU-28306 , CT-5252 )
Piperidinylethylindoles (e.g., Pip-T )
Pyrrolidinylethylindoles (e.g., Pyr-T , 5-MeO-pyr-T )
Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5-MeO-MPMI )
Benzofurans (e.g., 5-MeO-DiBF , dimemebfe (5-MeO-BFE) , mebfap )
Benzothiophenes (e.g., 3-APBT )
Indazoles (e.g., AL-38022A , O -methyl-AL-34662 )
Indenes (e.g., C-DMT )
Isotryptamines (e.g., 6-MeO-isoDMT , Ro60-0175 )
MYCO-005
Quinolinylethylamines (e.g., mefloquine )
Others: 2C-G-x (e.g., 2C-G-3 , 2C-G-5 )
β-Keto-2C-B (βk-2C-B)
β-Keto-2C-I (βk-2C-I)
β-Methyl-2C-B (BMB)
(e.g., BOB , BOD , BOH-2C-B )
(e.g., HOT-2 , HOT-7 , HOT-17 )
N -Ethyl-2C-B
(e.g., 2CD-2-ETO , 2CD-5-ETO , 2CE-5-ETO , 2CE-5iPrO , 2CT2-5-ETO , ASR-2001 (2CB-5PrO) )
Others
2-TOET
2-TOM
25B-NAcPip
4-HA
5-TOET
5-TOM
Benzofurans (e.g., 5-APB , 5-APDB , 6-APB , 6-APDB , F , F-2 , F-22 )
Benzothiophenes (e.g., 5-APBT , 6-APBT )
CT-5172
DMAs (e.g., 2,4-DMA , 3,4-DMA )
Fenfluramine
MMA (3-MeO-4-MA)
Norfenfluramine
(e.g., 25D-NM-NDEAOP , DOB-NDEPA , DOI-NDEPA , DOM-NDEPA , DOTFM-NDEPA , M-NDEPA , TMA-2-NDEPA )
PMA (4-MA)
(e.g., TMA-3 , TMA-4 , TMA-5 , TMA-6 )
TOMSO
ZDCM-04
1-Aminomethylindanes (e.g., 2CB-Ind , jimscaline )
2-Aminoindanes (e.g., DOM-AI )
3-Phenylpiperidines (e.g., LPH-5 , LPH-48 )
Benzazepines (e.g., lorcaserin )
Benzocyclobutenes (e.g., 2CBCB-NBOMe , TCB-2 , tomscaline )
Benzoxepins (e.g., BBOX , IBOX , TFMBOX )
DMBMPP (juncosamine)
Ergolines /lysergamides (e.g., LSD )
Glaucine
IHCH-7113
Partial ergolines (e.g., NDTDI , DEIMDHPCA , DEMPDHPCA , DEMTMPDHPCA , DEMNDHPCA )
Phenylcyclopropylamines (e.g., DMCPA , TMT )
Phenyloxazolamines (aminorexes ) (e.g., 2C-B-aminorex )
Z3517967757
ZC-B
Others
Arylpiperazines (e.g., 2C-B-PP , 2-NP , mCPP , MK-212 , ORG-12962 , pCPP , pFPP , quipazine , TFMPP )
Dihydrobenzoxazines (e.g., efavirenz )
Phenoxyethylamines (e.g., CT-4719 , ORG-37684 )
Quinazolinylethylamines (e.g., RH-34 )
Natural sources
Tryptamines: Acacia spp. (e.g., Acacia acuminata , Acacia confusa )
Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna) , Dipolopterys cabrerana (chaliponga, chacruna) , Mimosa tenuiflora (Mimosa hostilis ; jurema) )
Brosimum (e.g., Brosimum acutifolium (takini) )
Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene) , Anadenanthera colubrina (vilca, cebil) )
Incilius alvarius (Bufo alvarius ; Colorado River toad, Sonoran Desert toad; bufo)
Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis , Psilocybe mexicana (teonanacatl) )
Lysergamides: Achnatherum robustum (sleepy grass)
Epichloë spp.
Ergot (Claviceps ) (e.g., Claviceps purpurea , Claviceps paspali )
Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea ) , Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa , Turbina Corymbosa ) , Argyreia nervosa (Hawaiian baby woodrose; HBWR) )
Periglandula spp. (e.g., Periglandula ipomoeae , Periglandula clandestina )