5-MeO-NMT
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477225048
| ImageFile = 5-MeO-NMT.svg
| ImageSize = 200px
| PIN = 2-(5-Methoxy-1H-indol-3-yl)-N-methylethan-1-amine
| OtherNames = 5-Methoxy-N-methyltryptamine
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 15360
| InChI = 1/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3
| InChIKey = NFDDCRIHMZGWBP-UHFFFAOYAI
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 58579
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NFDDCRIHMZGWBP-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 2009-03-2
| CASNo_Comment = (freebase)
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 2426-68-8
| CASNo1_Comment = (hydrochloride)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YBO217L5YV
| UNII_Comment = (freebase)
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 3390M5391J
| UNII1_Comment = (hydrochloride)
| PubChem = 16184
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 189635
| SMILES = CNCCC1=CNC2=CC=C(C=C21)OC
}}
|Section2={{Chembox Properties
| C=12 | H=16 | N=2 | O=1
| Appearance =
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|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
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5-MeO-NMT, also known as 5-methoxy-N-methyltryptamine, is an organic chemical compound, being the 5-methoxy analogue of N-methyltryptamine (NMT). It was first isolated from Phalaris arundinacea (reed canary grass) and also occurs in other species such as Virola species and Bufo alvarius skin.{{cite journal|last1=Wilkinson|first1=S.|title=428. 5-Methoxy-N-methyltryptamine: a new indole alkaloid from Phalaris arundinacea L.|journal=Journal of the Chemical Society (Resumed)|date=1958|pages=2079|doi=10.1039/jr9580002079}} The compound has been synthesized by Alexander Shulgin and reported in his book TiHKAL.[http://www.erowid.org/library/books_online/tihkal/tihkal42.shtml 5-MeO-NMT Entry in TIHKAL]
Use and effects
Shulgin included 5-MeO-NMT as an entry in TiHKAL. However, he does not appear to have tried it and states that the dosage and duration of the compound are unknown. In any case, Shulgin stated that it would be expected to be rapidly metabolized by monoamine oxidase and that it would likely only be active parenterally.
Pharmacology
5-MeO-NMT is a potent agonist of the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors. It is a full agonist or near-full agonist of all of these receptors except for the serotonin 5-HT2A receptor, where it is a partial agonist. The drug is also a very weak serotonin releasing agent.{{cite journal | vauthors = Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB | title = Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes | journal = Psychopharmacology (Berl) | volume = 231 | issue = 21 | pages = 4135–4144 | date = October 2014 | pmid = 24800892 | pmc = 4194234 | doi = 10.1007/s00213-014-3557-7 | url = }}
5-MeO-NMT does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.{{cite journal | vauthors = Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, Golen JA, Chadeayne AR, Manke DR, Blough BE, McCorvy JD, Baumann MH | title = Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice | journal = ACS Chem Neurosci | volume = 15| issue = 24| pages = 4458–4477| date = December 2024 | pmid = 39636099 | doi = 10.1021/acschemneuro.4c00513 | url = }} On the other hand, it does induce serotonin 5-HT1A receptor-mediated hypothermia and hypolocomotion.
Chemistry
Notable analogues of 5-MeO-NMT include NMT, 5-MeO-NET, 5-MeO-NiPT, norpsilocin (4-HO-NMT), baeocystin (4-PO-NMT), 4-HO-NALT, and 5-MeO-NBpBrT, among others. 5-MeO-NMT is the N-monodemethylated analogue of 5-MeO-DMT.
Society and culture
=Legal status=
==United States==
In the United States, this substance is a Schedule 1 analogue of bufotenin.{{Citation needed|date=April 2025}}
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/5042 5-MeO-NMT - Isomer Design]
- [https://www.erowid.org/library/books_online/tihkal/tihkal42.shtml 5-MeO-NMT - Erowid]
- [https://isomerdesign.com/pihkal/read/tk/42 5-MeO-NMT - TiHKAL - Isomer Design]
- [https://bitnest.netfirms.com/external/SST/118-121 5-Methoxy-N-methyltryptamine (5-MeO-NMT) - Trout's Notes]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Monoamine releasing agents}}
{{Tryptamines}}
Category:N-Monoalkyltryptamines