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5-MeO-AMT

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5-MeO-AMT
Clinical data
Other names5-MeO-AMT; 5-Methoxy-α-methyltryptamine; α,O-Dimethylserotonin; Alpha-O
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F2 (Prohibited psychotropics)[2]
  • CA: Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: The DEA considers 5-MeO-AMT a controlled substance analogue.[1]
  • Illegal in Sweden and Florida
Identifiers
  • 1-(5-methoxy-1H-indol-3-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H16N2O
Molar mass204.273 g·mol−1
3D model (JSmol)
Melting point216 to 218 °C (421 to 424 °F)
  • N[C@@H](C)CC1=CNC(C=C2)=C1C=C2OC
  • InChI=1S/C12H16N2O/c1-8(13)5-9-7-14-12-4-3-10(15-2)6-11(9)12/h3-4,6-8,14H,5,13H2,1-2H3 checkY
  • Key:OGNJZVNNKBZFRM-UHFFFAOYSA-N checkY
  (verify)

5-MeO-αMT, or 5-methoxy-α-methyltryptamine, also known as α,O-dimethylserotonin (Alpha-O), is a serotonergic psychedelic of the tryptamine family. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.

Recreational use

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5-MeO-AMT blotters.

5-MeO-AMT is supposedly sold in 4 mg 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.[3][4]

The most common route of administration for 5-MeO-AMT is orally. Anecdotal reports, however, have described snorting or smoking the substance. Intravenous (IV) and intramuscular (IM) routes are rarely, if ever, used outside research settings due to the high potency, powerful effects and quicker onset.

Effects

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Tabs of gelatin containing 5-MeO-AMT.

The effects of 5-MeO-AMT occur at 4–7 mg orally for most users.

Erowid lists the following effects:[5]

Positive

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  • Increased energy
  • Improved mood heading into euphoria at higher doses
  • Increased sociability, gregariousness
  • Increased giggling and laughter
  • Increased sense of creative thinking
  • Increased pleasure from sense of touch
  • Intensification of sex for some users

Neutral

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  • Lightheadedness
  • Brightening of colors
  • Visuals including motion, waves, breathing walls, etc. (usually at higher doses, over 4–5 mg)
  • Increased attention to detail
  • Auditory distortions and/or hallucinations (usually at higher doses)

Negative

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  • Headache
  • Body fatigue
  • Chills from elevated body temperature (potential dehydration)
  • Stress and extreme fatigue from long duration of effects.
  • Nausea, diarrhea
  • Vomiting
  • Difficulty sleeping or resting for 12–24 hours after ingestion.
  • Paranoia, irritability, anxiety (increasing with dose).
  • Delusional, aggressive, or dissociated behaviour at very high doses (20+ mg)
  • Risk of death

Dangers

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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.[6][7] 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.[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.[8]

Pharmacology

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Pharmacodynamics

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5-MeO-AMT activities
Target Affinity (Ki, nM)
5-HT1A 46–194 (Ki)
680 (EC50Tooltip Half-maximal effective concentration)
5-HT1B 417 (rat)
5-HT2A 3.1–34 (Ki)
2–8.4 (EC50)
5-HT2B 4 (EC50)
5-HT2C 90
α1A >12,000
α2A 11,000
D1 >25,000
D2 >25,000
D3 >25,000
H1 >25,000
TAAR1 1,100–4,800 (rodent)
SERTTooltip Serotonin transporter 8,270–12,000 (Ki)
1,980–17,000 (IC50Tooltip half-maximal inhibitory concentration)
460 (EC50)
NETTooltip Norepinephrine transporter >22,000 (Ki)
37,000–78,000 (IC50)
8,900 (EC50)
DATTooltip Dopamine transporter >26,000 (Ki)
2,690–43,000 (IC50)
1,500 (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [9][10][11][12][13]

5-MeO-AMT acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT1A, 5-HT2A, and 5-HT2B receptors, among others.[11][10] Its EC50Tooltip half-maximal effective concentration at the serotonin 5-HT2A receptor has been found to be 2 to 8.4 nM.[11][10] In relation to this, it is an extremely potent agonist of the serotonin 5-HT2A receptor in vitro, showing the highest potency of any other tryptamine assessed in one study.[10] Its potency in activating the serotonin 5-HT2A receptor was 38-fold higher than that of dimethyltryptamine (DMT) and 361-fold higher than that of psilocin in the same study.[10] It is also a highly potent agonist of the serotonin 5-HT2B receptor, with an EC50 of 4 nM.[10]

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.[14][15][16][12] Accordingly, whereas the EC50 values of αMT for induction of monoamine release are 22 to 68 nM for serotonin, 79 to 112 nM for norepinephrine, and 79 to 180 nM for dopamine, the EC50 values in the case of 5-MeO-AMT are 460 nM for serotonin, 8,900 nM for norepinephrine, and 1,500 nM for dopamine.[12][15][10] Similarly, it is of very low potency as a monoamine reuptake inhibitor (IC50Tooltip half-maximal inhibitory concentration values >1,000 nM).[12][10] Considering the very high potency of 5-MeO-AMT in activating the serotonin 5-HT2A receptor, its weak activities as a monoamine releasing agent and reuptake inhibitor are of questionable significance.[12][15][10]

5-MeO-AMT produces the head-twitch response, a behavioral proxy of psychedelic effects, in animals, and this is reversed by the serotonin 5-HT2A receptor antagonist ketanserin.[17] 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.[18][11] The drug 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.[11][17] 5-MeO-AMT is known to produce sympathomimetic effects, but these effects likely depend on serotonin 5-HT2A receptor activation rather than on monoamine release or reuptake inhibition.[10] Other serotonergic psychedelics are also well-known to produce sympathomimetic effects.[19][20][21]

Chemistry

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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 looked at as the tryptamine homologues of the amphetamines (α-methylated phenethylamines).

5-MeO-AMT is soluble in ethanol.

History

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5-MeO-AMT was first described in the scientific literature by 1980.[22] It was described by Alexander Shulgin and colleagues.[22]

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Australia

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5-MeO-AMT is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[23] 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.[23]

Sweden

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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.[24]

United Kingdom

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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

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5-MeO-AMT is unscheduled at the federal level in the United States.[25] However, the DEA considers the chemical a controlled substance analogue.[26] The agency’s opinion on this matter may change at any time.

Florida

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5-MeO-AMT is a Schedule I controlled substance in the state of Florida, making it illegal to buy, sell, or possess.[27]

See also

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References

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  1. ^ "5-MeO-AMT; Fast Facts". National Drug Intelligence Center. January 1, 2006. Archived from the original on June 3, 2023. Retrieved July 5, 2023.{{cite web}}: CS1 maint: bot: original URL status unknown (link)
  2. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. ^ Zimmerman MM (January–June 2003). "The Identification of 5-Methoxy-alpha-methyltryptamine (5-MeO-AMT)". Microgram Journal. 1. Drug Enforcement Administration. Archived from the original on 2011-09-18. Retrieved 2011-09-16.
  4. ^ "Police Reports of 5-MeO-AMT". Erowid Vault.
  5. ^ "5-MeO-AMT Vault: Effects". Erowid Vault.
  6. ^ "Reported LSD-Related death was not LSD". Erowid Vault. July 2007.
  7. ^ "5-MeO-AMT Hospitalizations & Possible Deaths". Erowid Vault. January 2007.
  8. ^ Brodwater T (13 December 2006). "Charges dropped in drug death". The Spokesman-Review.
  9. ^ Liu, Tiqing. "BindingDB BDBM50227458 CHEMBL2093088". BindingDB. Retrieved 29 November 2024.
  10. ^ a b c d e f g h i j Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). European Neuropsychopharmacology. 26 (8): 1327–1337. doi:10.1016/j.euroneuro.2016.05.001. PMID 27216487. S2CID 6685927.
  11. ^ a b c d e Gatch MB, Forster MJ, Janowsky A, Eshleman AJ (July 2011). "Abuse liability profile of three substituted tryptamines". J Pharmacol Exp Ther. 338 (1): 280–289. doi:10.1124/jpet.111.179705. PMC 3126641. PMID 21474568.
  12. ^ a b c d e Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  13. ^ Wang S, Zhu A, Paudel S, Jang CG, Lee YS, Kim KM (March 2023). "Structure-Activity Relationship and Evaluation of Phenethylamine and Tryptamine Derivatives for Affinity towards 5-Hydroxytryptamine Type 2A Receptor". Biomol Ther (Seoul). 31 (2): 176–182. doi:10.4062/biomolther.2022.096. PMC 9970836. PMID 36224112.
  14. ^ 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.
  15. ^ a b c Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorg Med Chem Lett. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
  16. ^ Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.
  17. ^ a b Abiero A, Botanas CJ, Sayson LV, Custodio RJ, de la Peña JB, Kim M, Lee HJ, Seo JW, Ryu IS, Chang CM, Yang JS, Lee YS, Jang CG, Kim HJ, Cheong JH (February 2019). "5-Methoxy-α-methyltryptamine (5-MeO-AMT), a tryptamine derivative, induces head-twitch responses in mice through the activation of serotonin receptor 2a in the prefrontal cortex". Behav Brain Res. 359: 828–835. doi:10.1016/j.bbr.2018.07.020. PMID 30053461.
  18. ^ Glennon RA, Jacyno JM, Young R (April 1983). "A comparison of the behavioral properties of (+/-)-, (-)-, and (+)-5-methoxy-alpha-methyltryptamine". Biol Psychiatry. 18 (4): 493–498. PMID 6860723.
  19. ^ Wsół A (December 2023). "Cardiovascular safety of psychedelic medicine: current status and future directions". Pharmacol Rep. 75 (6): 1362–1380. doi:10.1007/s43440-023-00539-4. PMC 10661823. PMID 37874530.
  20. ^ Neumann J, Dhein S, Kirchhefer U, Hofmann B, Gergs U (2024). "Effects of hallucinogenic drugs on the human heart". Front Pharmacol. 15: 1334218. doi:10.3389/fphar.2024.1334218. PMC 10869618. PMID 38370480.
  21. ^ Ley L, Holze F, Arikci D, Becker AM, Straumann I, Klaiber A, Coviello F, Dierbach S, Thomann J, Duthaler U, Luethi D, Varghese N, Eckert A, Liechti ME (October 2023). "Comparative acute effects of mescaline, lysergic acid diethylamide, and psilocybin in a randomized, double-blind, placebo-controlled cross-over study in healthy participants". Neuropsychopharmacology. 48 (11): 1659–1667. doi:10.1038/s41386-023-01607-2. PMC 10517157. PMID 37231080.
  22. ^ a b Kantor RE, Dudlettes SD, Shulgin AT (April 1980). "5-methoxy-alpha-methyltryptamine (alphs, o-dimethylserotonin), a hallucinogenic homolog of serotonin". Biol Psychiatry. 15 (2): 349–352. PMID 7417623.
  23. ^ a b "Poisons Standard". Federal Register of Legislation. Australian Government. October 2015.
  24. ^ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" [Ordinance amending the ordinance (1999: 58) on the prohibition of certain dangerous goods;] (PDF). Swedish Code of Statutes (in Swedish). 19 August 2004. SFS 2004:696.
  25. ^ "§1308.11 Schedule I." Diversion Control Division. Drug Enforcement Administration, U.S. Department of Justice. Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  26. ^ "5-MeO-AMT; Fast Facts". National Drug Intelligence Center. January 1, 2006. Archived from the original on June 3, 2023. Retrieved July 5, 2023.{{cite web}}: CS1 maint: bot: original URL status unknown (link)
  27. ^ "Chapter 893 - Drug Abuse Prevention and Control". Florida Statutes.
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