N1-Methyl-lysergic acid diethylamide

Chemical compound

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^Y
PubChem CID	165200
ChemSpider	144824^Y
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^Y Key:VQZYKSWQIQANKB-DNVCBOLYSA-N^Y
(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.

Hallucinogens

Psychedelics
(5-HT_2A
agonists)

Benzofurans

Lyserg‐
amides

Phenethyl‐
amines

2C-x

2C-B
2C-B-AN
2C-Bn
2C-Bu
2C-C
2C-CN
2C-CP
2C-D
2C-E
2C-EF
2C-F
2C-G
2C-G-1
2C-G-2
2C-G-3
2C-G-4
2C-G-5
2C-G-6
2C-G-N
2C-H
2C-I
2C-iP
2C-N
2C-NH2
2C-O
2C-O-4
2C-P
2C-Ph
2C-SE
2C-T
2C-T-2
2C-T-3
2C-T-4
2C-T-5
2C-T-6
2C-T-7
2C-T-8
2C-T-9
2C-T-10
2C-T-11
2C-T-12
2C-T-13
2C-T-14
2C-T-15
2C-T-16
2C-T-17
2C-T-18
2C-T-19
2C-T-20
2C-T-21
2C-T-22
2C-T-22.5
2C-T-23
2C-T-24
2C-T-25
2C-T-27
2C-T-28
2C-T-30
2C-T-31
2C-T-32
2C-T-33
2C-TFE
2C-TFM
2C-YN
2C-V

25x-NBx

25x-NB	25B-NB 25C-NB
25x-NB3OMe	25B-NB3OMe 25C-NB3OMe 25D-NB3OMe 25E-NB3OMe 25H-NB3OMe 25I-NB3OMe 25N-NB3OMe 25P-NB3OMe 25T2-NB3OMe 25T4-NB3OMe 25T7-NB3OMe 25TFM-NB3OMe
25x-NB4OMe	25B-NB4OMe 25C-NB4OMe 25D-NB4OMe 25E-NB4OMe 25H-NB4OMe 25I-NB4OMe 25N-NB4OMe 25P-NB4OMe 25T2-NB4OMe 25T4-NB4OMe 25T7-NB4OMe 25TFM-NB4OMe
25x-NBF	25B-NBF 25C-NBF 25D-NBF 25E-NBF 25H-NBF 25I-NBF 25P-NBF 25T2-NBF 25T7-NBF 25TFM-NBF
25x-NBMD	25B-NBMD 25C-NBMD 25D-NBMD 25E-NBMD 25F-NBMD 25H-NBMD 25I-NBMD 25P-NBMD 25T2-NBMD 25T7-NBMD 25TFM-NBMD
25x-NBOH	25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25F-NBOH 25H-NBOH 25I-NBOH 25P-NBOH 25T2-NBOH 25T7-NBOH 25TFM-NBOH
25x-NBOMe	25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe
Atypical structures	25B-N1POMe 25B-NAcPip 25B-NB23DM 25B-NB25DM 25C-NBCl 25C-NBOEt 25C-NBOiPr 25I-N2Nap1OH 25I-N3MT2M 25I-N4MT3M 25I-NB34MD 25I-NBAm 25I-NBBr 25I-NBMeOH 25I-NBTFM 2CBCB-NBOMe 2CBFly-NBOMe 4-EA-NBOMe 5-APB-NBOMe 5MT-NBOMe C30-NBOMe DOB-NBOMe DOI-NBOMe FECIMBI-36 MDPEA-NBOMe N-Ethyl-2C-B NBOMe-escaline NBOMe-mescaline ZDCM-04

25x-NMx

25B-NMe7BF
25B-NMe7BT
25B-NMe7Bim
25B-NMe7Box
25B-NMe7DHBF
25B-NMe7Ind
25B-NMe7Indz
25B-NMePyr
25I-NMe7DHBF
25I-NMeFur
25I-NMeTHF
25I-NMeTh

N-(2C)-fentanyl

N-(2C-B) fentanyl
N-(2C-C) fentanyl
N-(2C-D) fentanyl
N-(2C-E) fentanyl
N-(2C-G) fentanyl
N-(2C-H) fentanyl
N-(2C-I) fentanyl
N-(2C-IP) fentanyl
N-(2C-N) fentanyl
N-(2C-P) fentanyl
N-(2C-T) fentanyl
N-(2C-T-2) fentanyl
N-(2C-T-4) fentanyl
N-(2C-T-7) fentanyl
N-(2C-TFM) fentanyl

3C-x

4C-x

4C-B
4C-C
4C-D
4C-E
4C-I
4C-N
4C-P
4C-T-2

DOx

DOT
DOB
DOC
DOEF
DOET
DOF
DOI
DOiPR
DOM
DON
DOPR
DOTFM
MEM

HOT-x

MDxx

Mescaline (subst.)

TMAs

TMA
TMA-2
TMA-3
TMA-4
TMA-5
TMA-6

Others

2C-B-BUTTERFLY
2C-B-DragonFLY
2C-B-DragonFLY-NBOH
2C-B-FLY-NB2EtO5Cl
2CB-5-hemifly
2CB-Ind
2CD-5EtO
2-TOET
5-TOET
2-TOM
5-TOM
BOB
BOD
βk-2C-B
βk-2C-I
DESOXY
DMCPA
DMBMPP
DOB-FLY
Fenfluramine
Ganesha
Macromerine
MMA
TCB-2
TOMSO

Piperazines

Tryptamines

alpha-alkyltryptamines	4,5-DHP-α-MT 5-MeO-α-ET 5-MeO-α-MT α-ET α-MT
x-DALT	(Daltocin) 4-HO-DALT (Daltacetin) 4-AcO-DALT 5-MeO-DALT DALT
x-DET	(Ethacetin) 4-AcO-DET (Ethocin) 4-HO-DET 5-MeO-DET (T-9) DET (Ethocybin) 4-PO-DET
x-DiPT	(Ipracetin) 4-AcO-DiPT (Iprocin) 4-HO-DiPT 5-MeO-DiPT DiPT
x-DMT	4,5-DHP-DMT 2,N,N-TMT 4-AcO-DMT 4-HO-5-MeO-DMT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-DMT 5-N,N-TMT 7,N,N-TMT α,N,N-TMT (Bufotenin) 5-HO-DMT DMT Norbaeocystin (Psilocin) 4-HO-DMT (Psilocybin) 4-PO-DMT
x-DPT	(Depracetin) 4-AcO-DPT (Deprocin) 4-HO-DPT 5-MeO-DPT (The Light) DPT
Ibogaine-related	18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine
x-MET	(Metocin) 4-HO-MET (Metocetin) 4-AcO-MET 5-MeO-MET MET
x-MiPT	(Mipracetin) 4-AcO-MiPT (Miprocin) 4-HO-MiPT 5-Me-MiPT (Moxy) 5-MeO-MiPT MiPT
Others	4-HO-DBT 4-HO-EPT 4-HO-McPT (Lucigenol) 4-HO-MPMI (Meprocin) 4-HO-MPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MPMI Aeruginascin Baeocystin DBT DCPT EiPT EPT MPT PiPT

Others

AL-38022A
ALPHA
Dimemebfe
Efavirenz
Glaucine
Lorcaserin
M-ALPHA
RH-34
Also empathogens in general (e. g.: 5-APB, 5-MAPB, 6-APB and other substituted benzofurans).

Dissociatives
(NMDAR
antagonists)

Arylcyclo‐
hexylamines

Ketamine-related	2-Fluorodeschloroketamine Arketamine ((R)-ketamine) Deschloroketamine Ethketamine (N-Ethylnorketamine) Esketamine ((S)-ketamine) Ketamine Methoxetamine Methoxmetamine Methoxyketamine MXiPr Norketamine Tiletamine
PCP-related	2'-Oxo-PCE 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP BDPC Dieticyclidine (PCDE) Eticyclidine (PCE) PCPr Phencyclidine (PCP) Rolicyclidine (PCPy) Tenocyclidine (TCP)
Others	BTCP Gacyclidine PRE-084

Adamantanes

Diarylethylamines

Morphinans

Others

Deliriants
(mAChR
antagonists)

Others

Cannabinoids
(CB₁ agonists)

Natural

Synthetic

AM-x	AM-087 AM-251 AM-279 AM-281 AM-356 AM-374 AM-381 AM-404 AM-411 AM-630 AM-661 AM-678 AM-679 AM-694 AM-735 AM-855 AM-881 AM-883 AM-905 AM-906 AM-919 AM-926 AM-938 AM-1116 AM-1172 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-1710 AM-1714 AM-1902 AM-2201 AM-2212 AM-2213 AM-2232 AM-2233 AM-2389 AM-3102 AM-4030 AM-4054 AM-4056 AM-4113 AM-6545
CP x	CP 47,497 CP 55,244 CP 55,940 (±)-CP 55,940 (+)-CP 55,940 (-)-CP 55,940
HU-x	HU-210 HU-211 HU-239 HU-243 HU-308 HU-320 HU-331 HU-336 HU-345
JWH-x	JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-047 JWH-048 JWH-051 JWH-057 JWH-073 JWH-081 JWH-098 JWH-116 JWH-120 JWH-122 JWH-133 JWH-139 JWH-147 JWH-148 JWH-149 JWH-149 JWH-161 JWH-164 JWH-166 JWH-167 JWH-171 JWH-175 JWH-176 JWH-181 JWH-182 JWH-184 JWH-185 JWH-192 JWH-193 JWH-194 JWH-195 JWH-196 JWH-197 JWH-198 JWH-199 JWH-200 JWH-203 JWH-205 JWH-210 JWH-210 JWH-213 JWH-220 JWH-229 JWH-234 JWH-249 JWH-250 JWH-251 JWH-253 JWH-258 JWH-300 JWH-302 JWH-307 JWH-336 JWH-350 JWH-359 JWH-387 JWH-398 JWH-424
Misc. designer cannabinoids	4-HTMPIPO 5F-AB-FUPPYCA 5F-AB-PINACA 5F-ADB 5F-ADB-PINACA 5F-ADBICA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-NNE1 5F-PB-22 5F-SDB-006 A-796,260 A-836,339 AB-001 AB-005 AB-CHFUPYCA AB-CHMINACA AB-FUBINACA AB-PINACA ADAMANTYL-THPINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADBICA ADSB-FUB-187 AMB-FUBINACA APICA APINACA APP-FUBINACA CB-13 CUMYL-PICA CUMYL-PINACA CUMYL-THPINACA DMHP EAM-2201 FAB-144 FDU-PB-22 FUB-144 FUB-APINACA FUB-JWH-018 FUB-PB-22 FUBIMINA JTE 7-31 JTE-907 Levonantradol MDMB-CHMICA MDMB-CHMINACA MDMB-FUBINACA MEPIRAPIM MAM-2201 MDA-19 MN-18 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan NM-2201 NNE1 Org 28611 Parahexyl PTI-1 PTI-2 PX-1 PX-2 PX-3 QUCHIC QUPIC RCS-4 RCS-8 SDB-005 SDB-006 STS-135 THC-O-acetate THC-O-phosphate THJ-018 THJ-2201 UR-144 WIN 55,212-2 XLR-11

D₂ agonists

Apomorphine
Aporphine
Bromocriptine
Cabergoline
Lisuride
LSD
Memantine
Nuciferine
Pergolide
Phenethylamine
Piribedil
Pramipexole
Ropinirole
Rotigotine
Salvinorin A
Also indirect D₂ agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABA_A
enhancers

Inhalants
(Mixed MOA)

κOR agonists

Oneirogens

Others

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)