5-MeO-NMT

Last updated

5-MeO-NMT
5-MeO-NMT.svg
5-MeO-NMT 3D.png
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 tested 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)
1.1–220 (EC50 Tooltip half-maximal effective concentration)
72–111% (Emax Tooltip maximal efficacy)
5-HT1B 23
5-HT1D 3
5-HT1E 212
5-HT2A 79 (Ki)
3.8–6.4 (EC50)
84–113% (Emax)
5-HT2B 11 (Ki)
8.8–12 (EC50)
94% (Emax)
5-HT2C 116 (Ki)
1.2–13 (EC50)
104% (Emax)
5-HT3 IA
5-HT5A 60
5-HT6 25
5-HT7 7
α2A 1,543
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]

There is conflicting data on its effects in mammals. In a study in 1964, Taborsky and McIsaac found 5-methoxy-NMT to have a 'moderately disruptive effect on conditioned behavior' in rats. [5] Another study found it 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. [6]

Chemistry

Synthesis

The chemical synthesis of 5-MeO-NMT has been described. [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. 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, et al. (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chemical Neuroscience. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID   39636099.
  5. ↑ Taborsky RG, Mcisaac WM (March 1964). "The relationship between the metabolic fate and pharmacological action of 5-methoxy-N-methyltryptamine". Biochemical Pharmacology. 13 (3): 531–534. doi:10.1016/0006-2952(64)90174-1. PMID   14157616.
  6. ↑ 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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