5-MeO-AMT

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5-MeO-αMT, also known as 5-methoxy-α-methyltryptamine or as α,O-dimethylserotonin (α,O-DMS or Alpha-O), is a psychedelic drug of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families.<ref name="TiHKAL" /> It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.<ref name="TiHKAL" /> The drug is said to be the most potent psychedelic of the simple indolealkylamines (i.e., tryptamines).<ref name="Vangveravong1994">Template:Cite web</ref> It is taken orally and is used at doses of 2 to 4Template:Nbspmg.<ref name="Vangveravong1994" /><ref name="TiHKAL">Template:CiteTiHKAL</ref>

Use and effects

File:5meoamtcheck.jpg

5-MeO-AMT blotters.

File:5meo amt sample dea1.jpg

Tabs of gelatin containing 5-MeO-AMT.

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin lists the dose range of 5-MeO-AMT as 2.5 to 4.5Template:Nbspmg and its duration as 12 to 18Template:Nbsphours.<ref name="TiHKAL" /> However, a wider dose range of 0.5 to 15Template:Nbspmg has also been reported.<ref name="LuethiLiechti2018">Template:Cite journal</ref><ref name="HalberstadtChathaKlein2020">Template:Cite journal</ref>

5-MeO-AMT has supposedly been sold as 4Template:Nbspmg tablets by the street name Alpha-O and taken as a recreational drug. Since the DEA arrests of the makers of a huge percentage of the United States' LSD in 2000, 5-MeO-AMT may have occasionally been sold under the guise of LSD in liquid, sugar cube, or blotter form, though this may be due to DEA reports of finding it on sugar cubes and blotters like LSD.<ref name="Zimmerman2003">Template:Cite journal</ref><ref>Template:Cite web</ref>

Shulgin has described the effects of 5-MeO-AMT in TiHKAL.<ref name="TiHKAL" />

Overdose

If misrepresented as LSD, 5-MeO-AMT can be extremely dangerous; users may take a number of "hits" of 5-MeO-AMT, assuming that it is LSD. Unlike LSD, which is very safe in overdose, 5-MeO-AMT can be very harmful or fatal. Particularly sensitive individuals can experience symptoms of overdose at dosages in the normal (for most users) range — as low as 20 mg. This has led to at least a few hospitalizations and possibly more than one death.<ref>Template:Cite web</ref><ref>Template:Cite web</ref> It is likely that the overdose potential of the compound is due to its sympathomimetic effects, as the side effects noted in overdose cases include cardiac arrhythmia and seizure. It also seems that oral consumption is safer than insufflation.Template:Citation needed

Gloria Discerni, 18, died after overdosing on a drug initially believed to be LSD. Authorities learned months later that the drug wasn't LSD but a "designer drug" identified as 5-MeO-AMT.<ref>Template:Cite web</ref>

Pharmacology

Pharmacodynamics

5-MeO-AMT activities

Target	Affinity (Ki, nM)
5-HT1A	46–194 (Ki) 680 (Template:Abbrlink) 101% (Template:Abbrlink)
5-HT1B	417 (rat)
5-HT2A	3.1–34 (Ki) 2–8.4 (Template:Abbr) 84% (Template:Abbr)
5-HT2B	4 (Template:Abbr)
5-HT2C	90
α1A	>12,000
α2A	11,000
D1	>25,000
D2	>25,000
D3	>25,000
H1	>25,000
TAAR1	1,100 (Ki) (rat) 4,800 (Ki) (mouse) >10,000 (Template:Abbr) (human)
Template:Abbrlink	8,270–12,000 (Ki) 1,980–17,000 (Template:Abbrlink) 460 (Template:Abbr)
Template:Abbrlink	>22,000 (Ki) 37,000–78,000 (Template:Abbr) 8,900 (Template:Abbr)
Template:Abbrlink	>26,000 (Ki) 2,690–43,000 (Template:Abbr) 1,500 (Template:Abbr)
Template:Abbrlink	31,000 (Template:Abbr)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="BindingDB">Template:Cite journal</ref><ref name="RickliMoningHoener2016">Template:Cite journal</ref><ref name="GatchForsterJanowsky2011" /><ref name="NagaiNonakaKamimura2007" /><ref name="WangZhuPaudel2023">Template:Cite journal</ref><ref name="WagmannBrandtKavanagh2017" /><ref name="SimmlerBuchyChaboz2016">Template:Cite journal</ref>

5-MeO-AMT acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT_1A, 5-HT_2A, and 5-HT_2B receptors, among others.<ref name="GatchForsterJanowsky2011">Template:Cite journal</ref><ref name="RickliMoningHoener2016" /> Its Template:Abbrlink at the serotonin 5-HT_2A receptor has been found to be 2 to 8.4Template:NbspnM.<ref name="GatchForsterJanowsky2011" /><ref name="RickliMoningHoener2016" /> In relation to this, it is an extremely potent agonist of the serotonin 5-HT_2A receptor in vitro, showing the highest potency of any other tryptamine assessed in one study.<ref name="RickliMoningHoener2016" /> Its potency in activating the serotonin 5-HT_2A receptor was 38-fold higher than that of dimethyltryptamine (DMT) and 361-fold higher than that of psilocin in the same study.<ref name="RickliMoningHoener2016" /> It is also a highly potent agonist of the serotonin 5-HT_2B receptor, with an Template:Abbr of 4Template:NbspnM.<ref name="RickliMoningHoener2016" />

Whereas tryptamine, serotonin (5-hydroxytryptamine), and αMT show potent activity as monoamine releasing agents, including of serotonin, norepinephrine, and/or dopamine, the monoamine-releasing activity of 5-methoxylated tryptamine derivatives, like 5-methoxytryptamine, 5-MeO-NMT, and 5-MeO-DMT among others, is dramatically reduced or abolished.<ref name="BloughLandavazoDecker2014">Template:Cite journal</ref><ref name="BloughLandavazoPartilla2014">Template:Cite journal</ref><ref name="RothmanBaumann2006">Template:Cite journal</ref><ref name="NagaiNonakaKamimura2007">Template:Cite journal</ref><ref name="GatchForsterJanowsky2011" /> Accordingly, whereas the Template:Abbr values of αMT for induction of monoamine release are 22 to 68Template:NbspnM for serotonin, 79 to 112Template:NbspnM for norepinephrine, and 79 to 180Template:NbspnM for dopamine, the Template:Abbr values in the case of 5-MeO-AMT are 460Template:NbspnM for serotonin, 8,900Template:NbspnM for norepinephrine, and 1,500Template:NbspnM for dopamine.<ref name="NagaiNonakaKamimura2007" /><ref name="BloughLandavazoPartilla2014" /><ref name="RickliMoningHoener2016" /> Similarly, it is of very low potency as a monoamine reuptake inhibitor (Template:Abbrlink values >1,000Template:NbspnM).<ref name="NagaiNonakaKamimura2007" /><ref name="RickliMoningHoener2016" /> Considering the very high potency of 5-MeO-AMT in activating the serotonin 5-HT_2A receptor, its weak activities as a monoamine releasing agent and reuptake inhibitor are of questionable significance.<ref name="NagaiNonakaKamimura2007" /><ref name="BloughLandavazoPartilla2014" /><ref name="RickliMoningHoener2016" /><ref name="GatchForsterJanowsky2011" />

5-MeO-AMT is a weak monoamine oxidase A (MAO-A) inhibitor, with an Template:Abbr of 31,000Template:NbspnM.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019">Template:Cite journal</ref><ref name="WagmannBrandtKavanagh2017">Template:Cite journal</ref> For comparison, the Template:Abbr of AMT for MAO-A inhibition was 380Template:NbspnM (~82-fold more potent than 5-MeO-AMT)<ref name="Reyes-ParadaIturriaga-VasquezCassels2019" /><ref name="WagmannBrandtKavanagh2017" /> and the Template:Abbr values of amphetamine (and its enantiomers) for MAO-A inhibition have been reported to be 11,000 to 70,000Template:NbspnM.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019" />

5-MeO-AMT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and this is reversed by the serotonin 5-HT_2A receptor antagonist ketanserin.<ref name="AbieroBotanasSayson2019">Template:Cite journal</ref><ref name="HalberstadtChathaKlein2020" /><ref name="MayDantanarayanaZinke2006">Template:Cite journal</ref> It substitutes for other psychedelics such as DOM and LSD in animal drug discrimination tests, but does not substitute for entactogens like MDMA or psychostimulants like dextromethamphetamine or cocaine.<ref name="GlennonJacynoYoung1983">Template:Cite journal</ref><ref name="GatchForsterJanowsky2011" /> In contrast to other psychedelics, 5-MeO-AMT has been found to not fully substitute for other psychedelics including DOM, LSD, and dimethyltryptamine (DMT), but did partially generalize to LSD (67% responding).<ref name="GatchForsterJanowsky2011" /> This is analogous to findings with 5-MeO-DMT, which has a major serotonin 5-HT_2A receptor-mediated component to its discriminative stimulus properties.<ref name="ErmakovaDunbarRucker2022">Template:Cite journal</ref><ref name="ShenJiangWinter2010">Template:Cite journal</ref><ref name="WinterFilipinkTimineri2000">Template:Cite journal</ref> 5-MeO-AMT does not produce locomotor hyperactivity, behavioral sensitization, conditioned place preference, or self-administration, further indicating a lack of psychostimulant-like effects as well as misuse potential.<ref name="GatchForsterJanowsky2011" /><ref name="AbieroBotanasSayson2019" /> Instead, 5-MeO-AMT produces hypolocomotion.<ref name="GatchForsterJanowsky2011" /> 5-MeO-AMT is known to produce sympathomimetic effects, but these effects likely depend on serotonin 5-HT_2A receptor activation rather than on monoamine release or reuptake inhibition.<ref name="RickliMoningHoener2016" /> Other serotonergic psychedelics are also well known to produce sympathomimetic effects.<ref name="Wsół2023">Template:Cite journal</ref><ref name="NeumannDheinKirchhefer2024">Template:Cite journal</ref><ref name="LeyHolzeArikci2023">Template:Cite journal</ref>

Chemistry

5-MeO-AMT, also known as 5-methoxy-α-methyltryptamine, is a substituted tryptamine derivative. It is a derivative of tryptamine (T), 5-methoxytryptamine (5-MeO-T or 5-MT), and α-methyltryptamine (AMT or αMT) and is an analogue of other tryptamines like α-methylserotonin (5-HO-AMT) and 5-MeO-DMT. Some derivatives of 5-MeO-AMT include α,N-dimethyl-5-methoxytryptamine (5-MeO-α-Me-NMT or α,N,O-TMS) and α,N,N-trimethyl-5-methoxytryptamine (5-MeO-α-Me-DMT or α,N,N,O-TMS). As noted by Alexander Shulgin, the α-methylated tryptamines can be seen at as the tryptamine homologues of the amphetamines (α-methylated phenethylamines).

Properties

5-MeO-AMT is soluble in water and ethanol but not in ether.<ref name="Shulgin1979" />

Synthesis

The chemical synthesis of 5-MeO-AMT has been described.<ref name="TiHKAL" />

Analogues

Analogues of 5-MeO-AMT include α-methyltryptamine (AMT), 4-HO-AMT, α-methylserotonin (5-HO-AMT), 5-EtO-AMT, 5-AlO-AMT, 5-fluoro-AMT, 5-chloro-AMT, α,N,O-TMS (5-MeO-N-Me-AMT), α,N,N,O-TeMS (5-MeO-α,N,N-TMT), 5-MeO-DMT, 5-MeO-DPT, 5-MeO-DiPT, O-methyl-AL-34662 (indazole-5-MeO-AMT), and zalsupindole ((R)-N,N-dimethyl-5-MeO-isoAMT), among others.

History

5-MeO-AMT was first synthesized and described in the scientific literature in 1958.<ref name="ShulginNichols1978" /><ref name="Shulgin1979" /><ref name="PietraTacconi1958">Template:Cite journal</ref> Its psychedelic effects in humans were first observed in 1976 and were described by Alexander Shulgin and David E. Nichols and colleagues by 1978.<ref name="ShulginNichols1978">Template:Cite book</ref><ref name="Shulgin1979">Template:Cite journal</ref><ref name="KantorDudlettesShulgin1980">Template:Cite journal</ref>

Society and culture

Legal status

Australia

5-MeO-AMT is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).<ref name="Poisons Standard">Template:Cite web</ref> A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.<ref name="Poisons Standard" />

Finland

5-MeO-AMT is scheduled in the "government decree on psychoactive substances banned from the consumer market".<ref>Template:Cite web</ref>

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 5-MeO-αMT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Oct 1, 2004, in their regulation SFS 2004:696 listed as 5-metoxi-alfametyltryptamin (5-MeO-AMT), making it illegal to sell or possess.<ref>Template:Cite web</ref>

United Kingdom

5-MeO-αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT. This was following the events of 10 June 2014 when the Advisory Council on the Misuse of Drugs recommended that 5-MeO-αMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.

United States

5-MeO-AMT is unscheduled at the federal level in the United States.<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">Template:Cite web</ref> However, the DEA considers the chemical a controlled substance analogue.<ref name="5-MeO-AMT; Fast Facts"></ref> The agency's opinion on this matter may change at any time.

Florida

5-MeO-AMT is a Schedule I controlled substance in the state of Florida, making it illegal to buy, sell, or possess.<ref name="Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL">Template:Cite web</ref>

See also

• Substituted α-alkyltryptamine

External links

• 5-MeO-AMT - Isomer Design
• 5-MeO-AMT - Erowid
• The Big & Dandy 5-MeO-AMT Thread - Bluelight
• 5-MeO-AMT - Lycaeum
• 5-MeO-AMT - TiHKAL - Erowid
• 5-MeO-AMT - TiHKAL - Isomer Design
• DEA forensic journal on 5-MeO-AMT