:Lespedamine

{{Chembox

| ImageFile = Lespedamine.svg

| ImageSize = 200px

| PIN = 2-(1-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

| OtherNames = 1-Methoxy-DMT; 1-MeO-DMT; 1-Methoxydimethyltryptamine; 1-Methoxy-N,N-dimethyltryptamine

|Section1={{Chembox Identifiers

| CASNo = 4335-93-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6W73QAN9CK

| PubChem = 11138594

| ChemSpiderID = 9313707

| SMILES = O(n2c1ccccc1c(c2)CCN(C)C)C

| StdInChI = 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

| StdInChIKey = DXTZTYQDNUHCAB-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=13 | H=18 | N=2 | O=1

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|Section3={{Chembox Hazards

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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.{{cite journal |vauthors=Somei M, Yamada F, Kurauchi T, etal |title=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 |journal=Chem. Pharm. Bull. |volume=49 |issue=1 |pages=87–96 |date=January 2001 |pmid=11201232 |doi= 10.1248/cpb.49.87|url=https://kanazawa-u.repo.nii.ac.jp/?action=repository_action_common_download&item_id=15159&item_no=1&attribute_id=26&file_no=1|doi-access=free |hdl=2297/43978 |hdl-access=free }}{{cite journal | url=https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/jlac.19656820121 | doi=10.1002/jlac.19656820121 | title=Über Alkaloide, V Inhaltsstoffe vonLespedeza bicolor var.japonica, I. über Lespedamin, ein neues Alkaloid | journal=Justus Liebigs Annalen der Chemie | date=22 February 1965 | volume=682 | issue=1 | pages=212–218 | last1=Morimoto | first1=Hiroshi | last2=Oshio | first2=Haruji | url-access=subscription }} The alkaloid bears a close structural resemblance to the psychedelic alkaloid dimethyltryptamine (DMT) and it was speculated by Alexander Shulgin in TiHKAL that it might be psychoactive.{{cite book | vauthors = Shulgin A | title=Tihkal: The Continuation | publisher=Transform Press | year=1997 | isbn=978-0-9630096-9-2 | url=https://books.google.com/books?id=jl_ik66IumUC | access-date=17 August 2024 | at=[https://isomerdesign.com/pihkal/read/tk/6#5112 #6. DMT] | quote = 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? [...] }} No reports on lespedamine's biological activity are known to have been published. Hamilton Morris asked entheogen ethnobotanist Jonathan Ott about lespedamine and its possible activity during an interview, but Ott was unfamiliar with it.{{cite podcast | url=https://www.patreon.com/posts/podcast-28-talk-55653035 | title=PODCAST 28: A talk with Jonathan Ott | website=The Hamilton Morris Podcast | publisher=Patreon | host=Hamilton Morris | date=1 September 2021 | time= | access-date=20 January 2025 }}