5-MeO-MPMI Legal status
DE : NpSG (Industrial and scientific use only)
UK : Class A
5-Methoxy-3-{[(2R )-1-methylpyrrolidin-2-yl]methyl}-1H -indole
CAS Number PubChem CID ChemSpider UNII ChEMBL Formula C 15 H 20 N 2 O Molar mass 244.338 g·mol−1 3D model (JSmol )
CN1CCC[C@@H]1CC2=CNC3=C2C=C(C=C3)OC
InChI=1S/C15H20N2O/c1-17-7-3-4-12(17)8-11-10-16-15-6-5-13(18-2)9-14(11)15/h5-6,9-10,12,16H,3-4,7-8H2,1-2H3/t12-/m1/s1
Y Key:MKEGUJPBCIXABO-GFCCVEGCSA-N
Y
N Y (what is this?)
5-MeO-MPMI (also known as 5-Methoxy-N -methyl-(α,N -trimethylene)tryptamine ) is a tryptamine derivative that is a psychedelic drug. It was first developed by the team led by JE Macor in 1992,[1] and subsequently investigated by the team led by David Nichols from Purdue University in the late 1990s. This compound produces psychedelic-appropriate responding in animal tests with a similar potency to the amphetamine -derived psychedelic DOI , and has two enantiomers , with only the (R )-enantiomer being active.[2]
See also [ ]
5-MeO-pyr-T
4-HO-MPMI
4-HO-pyr-T
CP-135,807
MPMI
References [ ]
^ Macor JE, Blake J, Fox CB, Johnson C, Koe BK , Lebel LA, Morrone JM, Ryan K, Schmidt AW, Schulz DW, et al. (1992). "Synthesis and serotonergic pharmacology of the enantiomers of 3-[(N-methylpyrrolidin-2-yl)methyl]-5-methoxy-1H-indole: discovery of stereogenic differentiation in the aminoethyl side chain of the neurotransmitter serotonin". Journal of Medicinal Chemistry . 35 (23): 4503–5. doi :10.1021/jm00101a032 . PMID 1447752 .
^ Gerasimov M, Marona-Lewicka D, Kurrasch-Orbaugh DM, Qandil AM, Nichols DE (1999). "Further studies on oxygenated tryptamines with LSD-like activity incorporating a chiral pyrrolidine moiety into the side chain". Journal of Medicinal Chemistry . 42 (20): 4257–4263. CiteSeerX 10.1.1.690.4941 . doi :10.1021/jm990325u . PMID 10514296 .
Hallucinogens
Psychedelics (5-HT2A agonists)
Benzofurans
2C-B-FLY
2CBFly-NBOMe
5-MeO-BFE
5-MeO-DiBF
Bromo-DragonFLY
F-2
F-22
TFMFly
Lyserg‐ amides Phenethyl‐ amines
Piperazines Tryptamines
alpha -alkyltryptaminesx -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-Propionyloxy-DMT
5-AcO-DMT
5-Bromo-DMT
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 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
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 PCP-related Others
Diarylethylamines Morphinans
Dextrallorphan
Dextromethorphan
Dextrorphan
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Rotigotine
Salvinorin A Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine , methylphenidate ), releasing agents (amphetamine , methamphetamine ), and precursors (levodopa ).
GABAA enhancers
CI-966
Eszopiclone
Ibotenic acid
Muscimol (Amanita muscaria )
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Zolpidem
Zopiclone
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U-69,593
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Glaucine
Isoaminile
Noscapine
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Tryptamines
1-Methylpsilocin
2,alpha-DMT
2-Me-DET
2-Methyl-5-HT
2,N,N-TMT
4,5-DHP-DMT
4,5-MDO-DMT
4,5-MDO-DiPT
4-AcO-DALT
4-AcO-DET
4-AcO-DMT
4-AcO-DiPT
4-AcO-MET
4-AcO-DPT
4-AcO-MiPT
4-F-5-MeO-DMT
4-HO-5-MeO-DMT
4-HO-DBT
4-HO-DET
4-HO-DiPT
4-HO-DPT
4-HO-DSBT
4-HO-EPT
4-HO-MET
4-HO-McPT
4-HO-McPeT
4-HO-MiPT
4-HO-MPMI
4-HO-MPT
4-HO-pyr-T
4-HO-αMT
4-Me-αET
4-Me-αMT
4-MeO-DMT
4-MeO-MiPT
4-PrO-DMT
5,6-MeO-MiPT
5,6-MDO-DiPT
5,6-MDO-DMT
5,6-MDO-MiPT
5,7-Dihydroxytryptamine
5-BT
5-Bromo-DMT
5-CT
5-Chloro-αMT
5-Chloro-DMT
5-Ethoxy-αMT
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5-Ethyl-DMT
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5-Fluoro-DMT
5-Fluoro-EPT
5-Fluoro-MET
5-HO-αMT
5-HO-DiPT
5-HTP
5-MeS-DMT
5-Methoxytryptamine
5-MeO-7,N,N-TMT
5-MeO-2-TMT
5-MeO-αET
5-MeO-αMT
5-MeO-DALT
5-MeO-DBT
5-MeO-DET
5-MeO-DiPT
5-MeO-DMT
5-MeO-DPT
5-MeO-EiPT
5-MeO-EPT
5-MeO-MALT
5-MeO-MET
5-MeO-MiPT
5-MeO-MPMI
5-MeO-NMT
5-MeO-pyr-T
5-MeO-NBpBrT
5-Methyl-DMT
5-(Nonyloxy)tryptamine
6-Fluoro-αMT
6-Fluoro-DMT
6-Hydroxymelatonin
6-MeO-THH
7-Chloro-AMT
7-Methyl-α-ethyltryptamine
7-Methyl-DMT
Acetryptine
Aeruginascin
αET
Alpha,N-DMT
α,N,N-Trimethyltryptamine
Alpha,N,O-TMS
AL-37350A
αMT
Baeocystin
BNC-210
Bufotenidine
Bufotenin (5-HO-DMT)
BW-723C86
Convolutindole A
CP-132,484
DALT
DBT
Desformylflustrabromine
DET
DiPT
DPT
E-6801
E-6837
Ethocybin
EiPT
EMDT
EPT
FGIN-127
FGIN-143
Harmaline
HIOC
Ibogaine
Idalopirdine
Indorenate
Iprocin
Lespedamine
Luzindole
MET
Methylbutyltryptamine
MiPT
MPT
Miprocin
Melatonin
MPMI
MS-245
NAS
N-Ethyltryptamine
N-Feruloylserotonin
NMT
DMT
Norbaeocystin
Normelatonin
N-t-Butyltryptamine
O-4310
Oxypertine
Plakohypaphorine
PiPT
Psilocin (4-HO-DMT)
Psilocybin (4-PO-DMT)
Pyr-T
Rizatriptan
RU-28306
Serotonin
ST-1936
Sumatriptan
Tryptamine
Tryptophan
Yohimbine
Yuremamine
Zolmitriptan