From Wikipedia, the free encyclopedia
Lespedamine
Names
Preferred IUPAC name
2-(1-Methoxy-1H -indol-3-yl)-N ,N -dimethylethan-1-amine
Other names
1-Methoxy-DMT; 1-MeO-DMT; 1-Methoxydimethyltryptamine; 1-Methoxy-N ,N -dimethyltryptamine
Identifiers
ChemSpider
UNII
InChI=1S/C13H18N2O/c1-14(2)9-8-11-10-15(16-3)13-7-5-4-6-12(11)13/h4-7,10H,8-9H2,1-3H3
Key: DXTZTYQDNUHCAB-UHFFFAOYSA-N
O(n2c1ccccc1c(c2)CCN(C)C)C
Properties
C 13 H 18 N 2 O
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Lespedamine , also known as 1-methoxy-N ,N -dimethyltryptamine (1-methoxy-DMT or 1-MeO-DMT ), is an indole alkaloid and substituted tryptamine present in the plant Lespedeza bicolor [ 1] [ 2] psychedelic alkaloid dimethyltryptamine (DMT) and it was speculated by Alexander Shulgin in TiHKAL Tryptamines I Have Known and Loved ) that it might be psychoactive .[ 3] biological activity are known to have been published.[ 3] controlled substance in the United States , but may be considered a Schedule I controlled substance in this country as it is a positional isomer of 5-MeO-DMT .[ 4] [ 5]
^ Somei M, Yamada F, Kurauchi T, et al. (January 2001). "The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry" . Chem. Pharm. Bull . 49 (1): 87– 96. doi :10.1248/cpb.49.87 hdl :2297/43978 PMID 11201232 . ^ Morimoto, Hiroshi; Oshio, Haruji (22 February 1965). "Über Alkaloide, V Inhaltsstoffe vonLespedeza bicolor var.japonica, I. über Lespedamin, ein neues Alkaloid" Justus Liebigs Annalen der Chemie . 682 (1): 212– 218. doi :10.1002/jlac.19656820121 . ^ a b Shulgin A (1997). Tihkal: The Continuation #6. DMT . ISBN 978-0-9630096-9-2 . Retrieved 17 August 2024 . Several simple substitution derivatives of DMT are known. Those that are known to be psychedelic have their own recipes, of course, but the others will be summarized here. The 1-methyl homologue of DMT (1,N,N-trimethyltryptamine) can be prepared from DMT in KOH and DMSO, with CH3I. It forms a picrate salt which melts at 175–179 °C, and bioxalate, mp 174–176 °C. It is more toxic than DMT in rats, but has an identical serotonin binding capacity. The compound with a methoxy group substituent at the 1-position is called Lespedamine, 1-MeO-DMT. With an NO bond, this should be classified as a substituted hydroxylamine. I would love to know if anyone anywhere has ever tried smoking it. I suspect it might very well be active, but it is, to my knowledge, untried. I wonder why it deserves a trivial name, vis., Lespedamine? [...] ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF) , United States : U.S. Department of Justice : Drug Enforcement Administration (DEA): Diversion Control Division, January 2026^ Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances" . Federal Register .
Tryptamines
1-Methyl-DMT (1,N ,N -TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N ,N -TMT (2-methyl-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 4-Methyl-DMT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-DMT 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-DMT 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) DALT DAT DBT Desformylflustrabromine DET (T-9) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT McPT MET MiPT MPT MsBT N -Benzyltryptamine (T-NB, NB-T)N -DEAOP-NETN -DEAOP-NMTNAT NBoc-DMT (NB-DMT) NET/NETP NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 Zolmitriptan 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines
2-Methyl-5-HT 2-Methyl-5-MeO-DALT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-DPT 5-HO-MET 5-HO-NiPT 5-HTP (oxitriptan )5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N ,N -TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N ,N ,O -TMS; O -methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O ,N -DMS) 5-MeO-NsBT 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine; O -methylserotonin) 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-NOT 5-PhO-T (OVT2) 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ; N ,N ,N -TMS) Bufotenin (5-HO-DMT; N ,N -DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) IS-159 Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -Feruloylserotonin (moschamine)NB-5-MeO-DALT NB-5-MeO-MiPT Norbufotenin (5-HO-NMT; NMS) O -Acetylbufotenine (5-AcO-DMT)O -Pivalylbufotenine (5-t -BuCO-DMT)Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT) N -Acetyltryptaminesα-Alkyltryptamines
5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O -DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 α-Ketotryptamines Cyclized tryptamines
5-MeO-IsoqT Barettin BML-190 (indomethacin morpholinylamide) Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD )Harmala alkaloidsβ-carbolines (e.g., 5-methoxyharmalan , 6-MeO-THH , 6-methoxyharmalan , 9-Me-BC , β-carboline (norharman) , fenharmane , harmaline , harmalol , harmane , harmine , LY-266,097 , pinoline , tetrahydroharmine , tryptoline )Iboga alkaloidsibogaine , ibogamine , noribogaine , tabernanthine )Ibogalogs (e.g., catharanthalog , fluorogainalog , ibogainalog , ibogaminalog (DM-506) , LS-22925 , noribogainalog , noribogaminalog , PHA-57378 , PNU-22394 , tabernanthalog )Imidazolylindoles (e.g., AGH-107 , AGH-192 , AH-494 )Metralindole Morpholinylethylindoles (e.g., mor-T , 5-MeO-mor-T )Partial ergolines and lysergamides (e.g., NDTDI , RU-27849 , RU-28251 , RU-28306 , FHATHBIN , LY-178210 , Bay R 1531 (LY-197206) , LY-293284 , 10,11-seco-LSD , 10,11-secoergoline (α,N -Pip-T) , CT-5252 )Pertines (e.g., alpertine , milipertine , oxypertine , solypertine )Piperidinylethylindoles (e.g., pip-T , 5-MeO-pip-T , indolylethylfentanyl )Pyrrolidinylethylindoles (e.g., pyr-T , 4-HO-pyr-T , 5-MeO-pyr-T , 4-F-5-MeO-pyr-T , L-760790 )Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5F-MPMI , 5-MeO-MPMI , CP-122288 , CP-135807 , eletriptan , MSP-2020 )Tetrahydrocarbazolamines (e.g., ciclindole , flucindole , frovatriptan , LY-344864 , ramatroban )Tetrahydropyridinylindoles (e.g., RS134-49 , RU-28253 , NEtPhOH-THPI )Tetrahydropyrroloquinolines (e.g., bufothionine , O -methylnordehydrobufoteninedehydrobufotenine )Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine ) Isotryptamines Related compounds
2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g., γ-carboline , alosetron , gevotroline , latrepirdine , lurosetron , mebhydrolin , tiflucarbine )Amedalin Benzindopyrine Benzofurans (e.g., 3-APB (1-oxa-AMT) , 5-MeO-DiBF (1-oxa-5-MeO-DiPT) , BPAP , 3-F-BPAP , dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) , mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) , MiPBF (1-oxa-MiPT) , oxa-noribogaine )Benzothiophenes (e.g., S-DMT (1-thia-DMT) , 3-APBT (1-thia-AMT) )Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g., HT , DMHT )I-32 IAL IN-399 Indazolethylamines (e.g., AL-34662 , AL-38022A , O -methyl-AL-34662VU6067416 , YM-348 )Indenylethylamines (e.g., C-DMT (1-carba-DMT) )Indolizinylethylamines (e.g., TACT908 (2ZEDMA) , 1ZP2MA , 1Z2MAP1O )Indolylaminopropanes (e.g., 1-API , 2-API , 4-API , 5-API (5-IT; PAL-571) , 6-API (6-IT) , 7-API )Iprindole Masupirdine Medmain Molindone Non-tryptamine triptans (e.g., avitriptan , LY-334370 , naratriptan )
Ondansetron Oxazinopyridoindoles (e.g., IHCH-8134 )Phenethylamines (e.g., phenethylamine , amphetamine )Piperidinylbenzimidazolines (e.g., benperidol , timiperone )Piperazinylbenzisothiazoles (e.g., lurasidone , perospirone , tiospirone , ziprasidone )Piperidinylbenzisoxazoles (e.g., iloperidone , milsaperidone , ocaperidone , paliperidone , risperidone )Piperidinylindoles (e.g., BRL-54443 , LY-334370 , naratriptan , sertindole , SN-22 )Pirlindole Pyridinylbenzimidazoles (e.g., droperidol )Pyridinylindoles (e.g., tepirindole )Pyridopyrroloquinoxalines (e.g., IHCH-7113 , IHCH-7079 , IHCH-7086 , lumateperone , deulumateperone , ITI-1549 )Pyrrolylethylamines (e.g., 2-pyrrolylethylamine (NEA) , 3-pyrrolylethylamine (3-NEA) , 3-pyrrolylpropylamine )Pyrrolopyridinylethylamines (e.g., WAY-208466 )Quinolinylethylamines (e.g., mefloquine )Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g., EMD-386088 , LY-367265 , RU-24,969 )Tetrahydropyridinylpyrrolopyridines (e.g., (R )-69 (3IQ) , (R )-70 , CP-93129 , CP-94253 )Tetrindole Tipindole Zilpaterol (RU-42173)
