N1-Methyl-lysergic acid diethylamide

N1-Methyl-lysergic acid diethylamide
Clinical data
Other names	MLD-41; N1-Methyl-Lysergic Acid Diethylamide
Routes of; administration	Oral
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
	IUPAC name (8β)-N,N-Diethyl-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide;
CAS Number	4238-85-1 ;
PubChem CID	165200;
ChemSpider	144824 ;
CompTox Dashboard (EPA)	DTXSID00895034 ;
Chemical and physical data
Formula	C21H27N3O
Molar mass	337.467 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N(CC)CC)[C@@H]3/C=C2/c4cccc1c4c(cn1C)C[C@H]2N(C3)C;
	InChI 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 ; Key:VQZYKSWQIQANKB-DNVCBOLYSA-N ;
	(verify)

N1-Methyl-lysergic acid diethylamide (MLD-41) is a derivative of LSD that has about one-third the psychoactive effects. It has been studied in cross-tolerance of LSD.^[1]

Metabolism of other 1-methylated-ergoloids to their secondary amine derivatives has been frequently noted in mammals.^[2]

References

^ 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): 151–4. doi:10.1080/00223980.1960.9916396.
^ 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.

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[1] 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): 151–4. doi:10.1080/00223980.1960.9916396.

[pmid3698092-2] 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.

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v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide 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 Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergol Mesulergine Metergoline MIPLA Methysergide 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 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 CY-208,243 Ergoline Lergotrile Nicergoline Pergolide
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)