From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
MLD-41 Other names MLD-41; MLD; N 1-Methyl-Lysergic Acid Diethylamide; 1-Methyl-LSD; 1-Methyl-N ,N -Diethyllysergamide; Methyl-LSD Routes of Oral [ 1] [ 2] Drug class Serotonergic psychedelic ; Hallucinogen
(8β)-N ,N -Diethyl-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide
CAS Number PubChem CID ChemSpider CompTox Dashboard (EPA ) Formula C 21 H 27 N 3 O Molar mass −1 3D model (JSmol )
O=C(N(CC)CC)[C@@H]3/C=C2/c4cccc1c4c(cn1C)C[C@H]2N(C3)C
InChI=1S/C21H27N3O/c1-5-24(6-2)21(25)15-10-17-16-8-7-9-18-20(16)14(12-22(18)3)11-19(17)23(4)13-15/h7-10,12,15,19H,5-6,11,13H2,1-4H3/t15-,19-/m1/s1
Y Key:VQZYKSWQIQANKB-DNVCBOLYSA-N
Y (verify)
MLD-41 , also known as 1-methyl-LSD , is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).[ 1] [ 2] psychoactive potency of LSD.[ 1] [ 2] cross-tolerance with LSD.[ 3] metabolism of other 1-methylated lysergamides to their secondary amine derivatives , for instance methysergide (1-methylmethylergometrine) conversion into methylergometrine , has been observed.[ 4] [ 5]
MLD-41 produces the head-twitch response , a behavioral proxy of psychedelic effects, in rodents, and with only slightly lower potency than LSD.[ 6]
Society and culture [ edit ] MLD-41 is not a controlled substance in Canada as of 2025.[ 7]
^ a b c Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF) . NIDA Res Monogr . 146 : 74– 91. PMID 8742795 . Archived from the original (PDF) on August 5, 2023. ^ a b c Hoffer A (1965). "D-Lysergic acid diethylamide (LSD): A review of its present status". Clin Pharmacol Ther . 6 : 183– 255. doi :10.1002/cpt196562183 . PMID 14288188 . ^ Abramson HA, Rolo A, Sklarofsky B, Stache J (January 1960). "Production of cross-tolerance to psychosis-producing doses of lysergic acid diethylamide and psilocybin". The Journal of Psychology . 49 (1): 151– 154. doi :10.1080/00223980.1960.9916396 . ^ Majrashi M, Ramesh S, Deruiter J, Mulabagal V, Pondugula S, Clark R, Dhanasekaran M (2017). "Multipotent and Poly-therapeutic Fungal Alkaloids of Claviceps purpurea". In Agrawal DC, Tsay HS, Shyur LF, Wu YC, Wang SY (eds.). Medicinal Plants and Fungi: Recent Advances in Research and Development . Medicinal and Aromatic Plants of the World. Vol. 4. pp. 229– 252. doi :10.1007/978-981-10-5978-0_8 . ISBN 978-981-10-5977-3 ISSN 2352-6831 . Metabolites of methysergide also exhibit pharmacological activity. Methylergometrine (one of methysergide's metabolites) is responsible for methysergide's therapeutic effects regarding migraine treatment (Müller-Schweinitzer and Tapparelli 1986). [...] The systemic availability of methysergide after oral administration is only 13%, due to a high degree of first-pass metabolism by N-1 demethylation to methylergometrine. After oral administration, the plasma concentrations of the metabolite are considerably higher than those of the parent drug, and the area under the plasma concentration curve (AUC) for methylergometrine is more than ten times greater than for methysergide. ^ Müller-Schweinitzer E, Tapparelli C (March 1986). "Methylergometrine, an active metabolite of methysergide". Cephalalgia: An International Journal of Headache . 6 (1): 35– 41. doi :10.1046/j.1468-2982.1986.0601035.x . PMID 3698092 . S2CID 5778173 . ^ Corne SJ, Pickering RW (1967). "A possible correlation between drug-induced hallucinations in man and a behavioural response in mice". Psychopharmacologia . 11 (1): 65– 78. doi :10.1007/BF00401509 . PMID 5302272 . ^ "Controlled Drugs and Substances Act" . Department of Justice Canada . Retrieved 19 January 2026 .
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others
Ergolines /lysergamides (e.g., LSD )Ibogalogs (e.g., ibogainalog , tabernanthalog , Pharm-136 )O -MethylnordehydrobufoteninePartial 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 , MSP-2020 )Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI) , NEtPhOH-THPI )
Others: 2C-B-AN 2C-DB 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) BOB , BOD , BOHB )HOT-2 , HOT-7 , HOT-17 )N -Ethyl-2C-B2CB-2-EtO , 2CD-2-EtO , 2CD-5-EtO , 2CE-5-EtO , 2CE-5iPrO , 2CT-5-EtO , 2CT2-2-EtO , 2CT7-2-EtO , ASR-2001 (2CB-5-PrO) ) Others
25B-NAcPip 2-DM-DOM 4-HA 5-DM-DOM Benzofurans (e.g., 5-APB , 5-APDB , 6-APB , 6-APDB , F , F-2 , F-22 )Benzothiophenes (e.g., 5-APBT , 6-APBT )BMB-202 CT-5172 DMAs (e.g., 2,4-DMA , 3,4-DMA )Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine 25D-NM-NDEAOP , DOB-NDEPA , DOI-NDEPA , DOM-NDEPA , DOTFM-NDEPA , M-NDEPA , TMA-2-NDEPA )PMA (4-MA) Thio-2Cs (e.g., 2C-5-TOET )Thio-DOx (e.g., 2-TOM , 5-TOET , 5-TOM , TOMSO )TMA-3 , TMA-4 , TMA-5 )ZDCM-04 (DOC-fenethylline)
1-Aminomethylindanes (e.g., 2CB-Ind , jimscaline )2-Aminoindanes (e.g., DOM-AI )3-Benzazepines (e.g., lorcaserin )3-Phenylpiperidines (e.g., LPH-5 , LPH-48 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )DMBMPP (juncosamine) Ergolines /lysergamides (e.g., LSD )Partial ergolines (e.g., NDTDI , DEIMDHPCA , DEMPDHPCA , DEMTMPDHPCA , DEMNDHPCA )Phenylcyclopropylamines (e.g., DMCPA , TMT )Phenyloxazolamines (aminorexes ) (e.g., 2C-B-aminorex )Pyridopyrroloquinoxalines (e.g., IHCH-7113 )Z3517967757 ZC-B
Others
9-Oxaergolines (e.g., RU-29717 )γ-Carbolines (e.g., tiflucarbine )Arylpiperazines (e.g., 2C-B-PP , 2-NP , mCPP , MK-212 , ORG-12962 , pCPP , pFPP , quipazine , TFMPP , VCU-1012 )Dihydrobenzoxazines (e.g., efavirenz )Phenoxyethylamines (e.g., CT-4719 , ORG-37684 )Pyridopyrroloquinoxalines (e.g., IHCH-7113 )Quinazolinylethylamines (e.g., RH-34 ) Natural sources
Tryptamines: Acacia spp.Acacia acuminata Acacia confusa Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna)Dipolopterys cabrerana (chaliponga, chacruna)Mimosa tenuiflora (Mimosa hostilis ; jurema)Brosimum 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.Periglandula ipomoeae Periglandula clandestina
Ergolines lysergines )Clavines Lysergamides
Psychedelic lysergamides: 1B-LSD 1BP-LSD 1Bz-LSD 1cP-AL-LAD 1cP-LSD 1cP-MiPLA 1D-AL-LAD 1D-LSD 1DD-LSD 1F-LSD 1Fe-LSD 1H-LSD 1P-AL-LAD 1P-ETH-LAD 1P-LSD 1P-MiPLA 1S-LSD 1SB-LSD (1BS-LSD) 1T-AL-LAD 1T-LSD 1V-LSD 2,3-Dihydro-LSD AL-LAD ALA-10 (1-acetyl-LAE) ALD-52 (1-acetyl-LSD) BU-LAD CPM-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) Diisopropyllysergamide (DiPLA) Dipropyllysergamide (DPL) Ergine (lysergic acid amide; LSA; LA-111; lysergamide) Ergometrine (ergonovine, ergobasine) ETH-LAD Ethylcyclopropyllysergamide (EcPLA) Ethylisopropyllysergamide (EiPLA) Ethylpropyllysergamide (EPLA; LEP-57) Ethyltrifluoroethyllysergamide (ETFELA) IP-LAD Isoergine (isolysergic acid amide; iso-LSA; iso-LA; isolysergamide) Isopropyllysergamide (iPLA; LAiP) Lysergic acid diethylamide (LSD; d -LSD; lysergide) Lysergic acid ethylamide (LAE-32, LAE) Lysergic acid hydroxyethylamide (LSH, LAH) Lysergic acid methylamide (LAM) Lysergic acid methylethylamide (LME-54) Lysergic acid morpholide (LSM-775) Lysergic acid propylamide (LAP) Lysergic acid pyrrolidide (LPD-824) Lysergic acid 2-butylamide (LSB) Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LA-Azetidine) Lysergic acid 2-pentylamide (2-LSP) Lysergic acid 3-pentylamide (LSP, 3-LSP) Methylergometrine (methylergonovine, methylergobasine; Methergine) Methylisopropyllysergamide (MiPLA) Methylpropyllysergamide (LAMPA, LMP-55) Methysergide (1-methylmethylergonovine; UML-491) MLA-74 (1-methyl-LAE) MLD-41 (1-methyl-LSD) MPD-75 (1-methyllysergic acid pyrrolidide) NBOMe-LAD OML-632 (1-hydroxymethyl-LSD) PARGY-LAD PRO-LAD TRALA-12 (didehydro-LSD; DDH-LSD) Ergopeptines Partial ergolines Related compounds Natural sources
