Methylisopropyllysergamide

Chemical compound

none

Legal statusLegal status

DE: NpSG (Industrial and scientific use only)
UK: Under Psychoactive Substances Act
US: Schedule I (isomer of LSD)
Illegal in France^[1]

Identifiers

IUPAC name

(8β)-N-Isopropyl-N,6-dimethyl-9,10-didehydroergoline-8-carboxamide

CAS Number

100768-08-9^Y

PubChem CID

57507938

UNII

AC6WQQ5Y4B

Chemical and physical dataFormulaC₂₀H₂₅N₃OMolar mass323.440 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C4N(C)C1Cc2c[nH]c(ccc3)c2c3C1=CC4C(=O)N(C)C(C)C

InChI

InChI=1S/C20H25N3O/c1-12(2)23(4)20(24)14-8-16-15-6-5-7-17-19(15)13(10-21-17)9-18(16)22(3)11-14/h5-8,10,12,14,18,21H,9,11H2,1-4H3
Key:ROICYBLUWUMJFF-UHFFFAOYSA-N

(verify)

Methylisopropyllysergamide (lysergic acid methylisopropyl amide, MIPLA) is an analogue of LSD that was originally discovered by Albert Hofmann at Sandoz during the original structure-activity research into LSD. It has subsequently been investigated in more detail by the team led by David E. Nichols at Purdue University. Methylisopropyllysergamide is a structural isomer of LSD, with the alkyl groups on the amide nitrogen having been subjected to a methylene shuffle. MIPLA and its ethylisopropyl homologue are the only simple N,N-dialkyl lysergamides that approach the potency of LSD itself, being around 1/3-1/2 the potency of LSD,^[2] while all other dialkyl analogues tested (dimethyl, dipropyl, methylethyl etc.) are only around 1/10 as potent as LSD,^[3] although some N-monoalkyl lysergamides such as the sec-butyl and t-butyl derivatives were also found to show an activity profile and potency comparable to LSD,^[4] and the mono-isopropyl derivative is only slightly weaker than MIPLA. Apart from its lower potency, the hallucinogenic effects of methylisopropyllysergamide are similar to those of LSD itself, and the main use for this drug has been in studies of the binding site at the 5-HT_2A receptor through which LSD exerts most of its pharmacological effects.^[5]

References

^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
^ Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (March 1994). "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology Biochemistry and Behavior. 47 (3): 667–73. doi:10.1016/0091-3057(94)90172-4. PMID 8208787. S2CID 16490010.
^ Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects" (PDF). Acta Physiologica et Pharmacologica Neerlandica. 8: 240–58. PMID 13852489.
^ US patent 2997470, Pioch RP, "Lysergic Acid Amides", published 1956-03-05, issued 1961-08-22
^ Nichols DE (2001). "LSD and its lysergamide cousins" (PDF). The Heffter Review of Psychedelic Research. 2. Santa Fe, New Mexico: Heffter Research Institute: 80–7.

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)