5-Methoxytryptamine

5-Methoxytryptamine
Clinical data
Other names5-MeO-T; 5-OMe-T; 5-MeOT; 5-MeO-TPA; 5-MT; MT; 5-Hydroxytryptamine methyl ether; Serotonin methyl ether; O-Methylserotonin; O-Methyl-5-HT; Mexamine; Meksamin; Mekasamin; PAL-234
Routes of
administration
Orally inactive[1][2]
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Pharmacokinetic data
MetabolismMAO-ATooltip Monoamine oxidase A
Identifiers
  • 2-(5-Methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.009.231 Edit this at Wikidata
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
  • O(c1cc2c(cc1)[nH]cc2CCN)C
  • InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3 checkY
  • Key:JTEJPPKMYBDEMY-UHFFFAOYSA-N checkY
  (verify)

5-Methoxytryptamine (5-MT, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or O-methylserotonin and as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin.[3] It has been shown to occur naturally in the body in low levels, especially in the pineal gland.[3][4] It is formed via O-methylation of serotonin or N-deacetylation of melatonin.[3][5][4]

5-MT is a highly potent and non-selective serotonin receptor agonist[6][7][8][9] and shows serotonergic psychedelic-like effects in animals.[10] However, it is inactive in humans, at least orally, likely due to rapid metabolism by monoamine oxidase (MAO).[1][2] The levels and effects of 5-MT are dramatically potentiated by monoamine oxidase inhibitors (MAOIs) in animals.[11][12][13][14][15][16]

Biosynthesis

5-MT can be formed by O-methylation of serotonin mediated by hydroxyindole O-methyltransferase (HIOMT) or by N-deacetylation of melatonin.[3][5] It is also a precursor of 5-MeO-DMT in some species.[3]

Pharmacology

Pharmacodynamics

5-MT activities
Target Affinity (Ki, nM)
5-HT1A 3.2 (Ki)
183–535 (EC50Tooltip half-maximal effective concentration
66–135% (EmaxTooltip maximal efficacy)
5-HT1B 0.75–38
5-HT1D 1.7–34
5-HT1E 3,151
5-HT1F 1,166
5-HT2A 4.8–724 (Ki)
0.503 (EC50)
119% (Emax)
5-HT2B 0.51–16
5-HT2C 45–943
5-HT3 >10,000 (non-human)
5-HT4 27–2,443
5-HT5A 98 (unknown)
5-HT6 18–88
5-HT7 0.5–5.0
MT1 >10,000
MT2 >10,000
SERTTooltip Serotonin transporter 4,000 (IC50Tooltip half-maximal inhibitory concentration)
2,169 (EC50)
NETTooltip Norepinephrine transporter >10,000 (IC50)
>10,000 (EC50)
DATTooltip Dopamine transporter >10,000 (IC50)
11,031 (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [6][7][8][9][17]

5-MT acts as an agonist of the serotonin 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors.[18][19][20][21][22][23][24]

It is an extremely potent serotonin 5-HT2A receptor agonist in vitro, with an EC50Tooltip half-maximal effective concentration of 0.503 nM.[8] This was more potent than any other tryptamine evaluated in two large series of compounds.[8][9] For comparison, 5-MeO-DMT had an EC50 of 3.87 nM (7.7-fold lower) and dimethyltryptamine (DMT) had an EC50 of 38.3 nM (76-fold lower).[9]

5-MT has been said to be 25- and 400-fold selective for the serotonin 5-HT2B receptor over the serotonin 5-HT2A and 5-HT2C receptors, respectively.[25]

5-MT, in contrast to the closely related melatonin, has no affinity for the melatonin receptors.[26][27] However, it may be converted into melatonin in the body, and hence may indirectly act as a melatonin receptor agonist.[3][5]

5-MT shows dramatically reduced activity as a monoamine releasing agent compared to tryptamine and serotonin.[8]

Effects in animals and humans

5-MT dose-dependently induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and this effect is reversed by serotonin 5-HT2A receptor antagonists.[10][28][29][30][31][15][16] As such, it may be a hallucinogen in humans.[32] 5-MT is only briefly mentioned in several places in Alexander Shulgin's TiHKAL and its psychoactive effects are not described.[33][34] Besides psychedelic-like effects, 5-MT produces a "hyperactivity syndrome" in rodents.[3][11][35] It produces various other effects in animals as well.[3]

Pharmacokinetics

Distribution

5-MT is able to cross the blood–brain barrier and enter the central nervous system with peripheral administration in animals.[11]

Metabolism

5-MT is metabolized by deamination by monoamine oxidase (MAO), specifically monoamine oxidase A (MAO-A) and to a much lesser extent by monoamine oxidase B (MAO-B).[12][13][14][36]

Brain levels of 5-MT following central administration of 5-MT in rats were potentiated by 20-fold by the MAO-A inhibitor clorgyline and by 5.5-fold by the MAO-B inhibitor selegiline.[13][12] Similarly, levels of serotonin and phenethylamine were also greatly elevated by these drugs.[12][13] In accordance with the potentiation of brain levels of 5-MT by MAOIs, the behavioral effects of centrally administered 5-MT in rats, for instance in the conditioned avoidance response test, are markedly enhanced by MAOIs, including by the dual MAO-A and MAO-B inhibitor iproniazid and by clorgyline and selegiline.[13]

Similarly to rat findings, pineal gland levels of endogenous 5-MT are dramatically elevated by the MAO-A inhibitor clorgyline and by the dual MAO-A and MAO-B inhibitor pargyline in hamsters, and plasma levels of exogenous 5-MT are greatly elevated by these MAOIs as well.[14] Conversely, selegiline was ineffective in elevating brain or plasma 5-MT levels in hamsters.[14]

The non-selective MAO-A and MAO-B inhibitor tranylcypromine has been frequently used to potentiate the effects of 5-MT in animal studies.[11][29][31][15][16]

5-MT is orally inactive in humans presumably due to rapid metabolism by MAO-A.[1][2]

Metabolites of 5-MT include 5-methoxyindole-3-acetic acid (5-MIAA) and 5-methoxytryptophol.[3][14] It may also be metabolized into melatonin.[3][5]

Chemistry

5-MT, also known as 5-methoxytryptamine or as 5-hydroxytrypamine O-methyl ether, is a substituted tryptamine and a derivative of serotonin (5-hydroxytryptamine) and precursor of melatonin (N-acetyl-5-methoxytryptamine).[37]

It is closely related to other 5-methoxylated tryptamines such as 5-MeO-NMT, 5-MeO-DMT, 5-MeO-DPT, 5-MeO-DiPT, 5-MeO-MiPT, 5-MeO-DALT, and 5-MeO-AMT. 5-MeO-AMT is orally active in humans, in contrast to 5-MT, and could be thought of as a sort of orally active form of 5-MT.[2] Some other notable analogues of 5-MT include tryptamine, 2-methyl-5-hydroxytryptamine, 5-benzyloxytryptamine, 5-carboxamidotryptamine, 5-(nonyloxy)tryptamine, α-methyl-5-hydroxytryptamine, acetryptine (5-acetyltryptamine), and isamide (N-chloroacetyl-5-methoxytryptamine), among others.

The predicted log P of 5-MT is 0.5 to 1.41.[37][38][39]

References

  1. ^ a b c Nichols DE (2012). "Structure–activity relationships of serotonin 5‐HT 2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X.
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  33. ^ Shulgin A (1997). TiHKAL: The Continuation (PDF). Transform Press. ISBN 978-0-9630096-9-2. Retrieved 2 November 2024. One of its most broadly studied properties is that of protecting an experimental animal against the damage of being exposed to radiation. It was unexpectedly observed that our essential and favorite neurotransmitter serotonin was every bit as effective as a radioprotective agent. In efforts to make this natural compound more accessible to the damaged animal, it was studied as the unacetylated Omethyl ether. This simple compound, 5-methoxytryptamine (5-MeO-T, or Mexamine) has been mentioned under the recipe for 5-MeO-DMT in its possible effects in potentiating CNS-active drugs. But here it deserves to be highlighted for its protection against radiation. Two structural modification directions of 5-methoxytryptamine have been thoroughly explored. [...] A A 5-MeO-T anti-radiation, not a psychedelic ? [...] Removal of both methyl groups from the nitrogen gives 5- methoxytryptamine (5-MeO-T) which has been explored most extensively by Soviet researchers as a treatment for exposure to radiation; this aspect of its action is discussed and expanded upon in the commentary under Melatonin. It is also known by the trade name Mexamine and has been looked at as a potentiator of centrally active drugs.
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Monument in London The Monument redirects here. For the house in California, see Monument House. For other uses, see Monument (disambiguation). View of the Monument, designed by Sir Christopher Wren Viewing platform at the top of the Monument The Monument to the Great Fire of London, more commonly known simply as the Monument, is a fluted Doric column in London, England, situated near the northern end of London Bridge. Commemorating the Great Fire of London, it stands at the junction of Monum...

Building in Edinburgh, ScotlandThe Oxford BarGeneral informationAddressEdinburgh, ScotlandCoordinates55°57′10.61″N 03°12′19.82″W / 55.9529472°N 3.2055056°W / 55.9529472; -3.2055056Opened1811Websiteoxfordbar.co.uk Listed Building – Category BOfficial name8 and 8A Young Street, the Oxford Bar, and 2 Young Street Lane South[1]Designated3 March 1966; 57 years ago (1966-03-03)[1]Reference no.LB40820[1] The Oxford ...

 

В Википедии есть статьи о других людях с именем Александр. Александрдр.-греч. Ἀλέξανδρος Дата рождения 303—298 годы до н. э. Место смерти Эллинистический Египет Страна  Македония Отец Деметрий I Полиоркет Мать Деидамия Александр (др.-греч. Ἀλέξανδρος ; в промежу...

 

Isla Salsipuedes Ubicación geográficaOcéano Pacífico Mar de CortésCoordenadas 28°43′34″N 112°57′19″O / 28.726111111111, -112.95527777778Ubicación administrativaPaís  MéxicoDivisión MexicaliEstado Baja CaliforniaCaracterísticas generalesGeología Isla volcánica[1]​Superficie 1.03[2]​Longitud 2.59 km[1]​Anchura máxima 0.69 km[1]​Punto más alto (18 metros)PoblaciónPoblación 0[3]​ hab.Densidad 0 hab./km²Mapa de loca...

Bronce Coordenadas de colorHTML #CD7F32RGB (r,g,b)B (205, 127, 50)CMYK (c, m, y, k)C (0, 38, 76, 20)HSV (h, s, v) (30°, 76%, 80%)Referencia [1]/Maerz and Paul[1]​B) Normalizado con rango [ 0 – 255 ] (byte)C) Normalizado con rango [ 0 – 100 ] (cien)[editar datos en Wikidata] El bronce es un color marrón metálico que se asemeja al metal de la aleación de bronce. El primer uso registrado de bronce como nombre de color en inglés fue en 1753.[2]​ Variaciones ...

 

WTA-toernooi van Toronto 2022 Winnares in het enkelspel, Simona Halep Officiële naam National Bank Open Editie 2022 (120e editie) Stad, land Toronto, Canada Locatie Sobeys Stadium Datum 8–14 augustus Auspiciën WTA Categorie WTA 1000 Prijzengeld US$ 2.527.250 Deelnemers 56 enkel, 32 kwal. / 28 dubbel Ondergrond hardcourt, buiten Tegelijk met ATP-toernooi van Montreal Winnaar enkel Simona Halep Winnaars dubbel Vlag van Verenigde Staten Cori GauffVlag van Verenigde Staten...

 

Strategi Solo vs Squad di Free Fire: Cara Menang Mudah!