5-MeO-NMT

Last updated
5-MeO-NMT
5-MeO-NMT.svg
Clinical data
Other names5-OMe-NMT; 5-Methoxy-N-methyltryptamine
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonin releasing agent
ATC code
  • None
Identifiers
  • 2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H16N2O
Molar mass 204.273 g·mol−1
3D model (JSmol)
  • CNCCC1=CNC2=CC=C(C=C21)OC
  • InChI=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 Yes check.svgY
  • Key:NFDDCRIHMZGWBP-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

5-MeO-NMT, also known as 5-methoxy-N-methyltryptamine, is an tryptamine alkaloid, 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. [1] [2] The compound has been synthesized by Alexander Shulgin and reported in his book TiHKAL (Tryptamines I Have Known and Loved). [1]

Contents

Use and effects

Alexander Shulgin included 5-MeO-NMT as an entry in his book TiHKAL (Tryptamines I Have Known and Loved). [1] However, he does not appear to have tried it and states that the dose and duration of the compound are unknown. [1] 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. [1]

Pharmacology

Pharmacodynamics

5-MeO-NMT activities
TargetAffinity (Ki, nM)
5-HT1A 7.9 (Ki)
220 (EC50 Tooltip half-maximal effective concentration)
72% (Emax Tooltip maximal efficacy)
5-HT1B 23
5-HT1D 3
5-HT1E 212
5-HT2A 79 (Ki)
3.8–4.2 (EC50)
84–113% (Emax)
5-HT2B 11 (Ki)
8.8 (EC50)
94% (Emax)
5-HT2C 116 (Ki)
13 (EC50)
104% (Emax)
5-HT3 IA
5-HT5A 60
5-HT6 25
5-HT7 7
D4 885
SERT 1,114a (EC50)
NET Tooltip Norepinephrine transporter>10,000a (EC50)
DAT Tooltip Dopamine transporter>10,000a (EC50)
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes:a = Neurotransmitter release. Sources: [3] [4]

5-MeO-NMT is a potent agonist of the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors. [4] It is a full agonist or near-full agonist of all of these receptors except for the serotonin 5-HT1A receptor, where it is a partial agonist. [4] It additionally displays a high affinity for multiple other serotonin receptors. [4] The drug is also a very weak serotonin releasing agent and has sub micromolar affinity for dopamine D4 receptor. [3] [4]

5-MeO-NMT does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and in some cases even reduced total HTRs. [4] On the other hand, it does induce serotonin 5-HT1A receptor-mediated hypothermia and hypolocomotion. [4] Earlier reports had stated that 5-MeO-NMT and its N-demethylated analogue 5-methoxytryptamine were inactive, but this proved not to be the case. [5]

Chemistry

Synthesis

The chemical synthesis of 5-MeO-NMT has been descibed. [1]

Analogues

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. [4] [3] [1] 5-MeO-NMT is the N-monodemethylated analogue of 5-MeO-DMT. [1]

Society and culture

United States

In the United States, this substance is a Schedule 1 analogue of bufotenin.[ citation needed ]

See also

References

  1. 1 2 3 4 5 6 7 8 5-MeO-NMT Entry in TIHKAL
  2. ↑ Wilkinson, S. (1958). "428. 5-Methoxy-N-methyltryptamine: a new indole alkaloid from Phalaris arundinacea L.". Journal of the Chemical Society (Resumed): 2079. doi:10.1039/jr9580002079.
  3. 1 2 3 Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC   4194234 . PMID   24800892.
  4. 1 2 3 4 5 6 7 8 Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, Golen JA, Chadeayne AR, Manke DR, Blough BE, McCorvy JD, Baumann MH (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID   39636099.
  5. ↑ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M. The same relationship holds with the 5-methoxy derivatives, the N-methyl compound and the parent tryptamine being metabolized by amine oxidases to an extent greater than 80 per cent (Kveder and Mcisaac, 1961; Taborsky and Mcisaac, 1964a) and being ineffective in altering animal behaviour (Smythies, Bradley, and Johnston, 1967), while 5-methoxy-N,N-dimethyltryptamine is resistant to oxidative deamination and is among the most potent of the hallucinogenic tryptamines.
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