Chemistry:5-MeO-NMT

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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]

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
Target Affinity (Ki, nM)
5-HT1A 7.9 (Ki)
1.1–220 (EC50)
72–111% (Emax)
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 >10,000a (EC50)
DAT >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

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 5-MeO-NMT Entry in TIHKAL
  2. ↑ "428. 5-Methoxy-N-methyltryptamine: a new indole alkaloid from Phalaris arundinacea L.". Journal of the Chemical Society (Resumed): 2079. 1958. doi:10.1039/jr9580002079. 
  3. ↑ 3.0 3.1 3.2 "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology 231 (21): 4135–4144. October 2014. doi:10.1007/s00213-014-3557-7. PMID 24800892. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 4.7 "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. December 2024. doi:10.1021/acschemneuro.4c00513. PMID 39636099. 
  5. ↑ "The relationship between the metabolic fate and pharmacological action of 5-methoxy-N-methyltryptamine". Biochemical Pharmacology 13 (3): 531–534. March 1964. doi:10.1016/0006-2952(64)90174-1. PMID 14157616. 
  6. ↑ "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. "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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