αあるふぁ-Methyltryptamine

From Wikipedia, the free encyclopedia
(Redirected from Alpha-methyltryptamine)
αあるふぁ-Methyltryptamine
Clinical data
Other namesIndopan; αあるふぁ-Methyl-3-indoleethanamine; 3-(2-Aminopropyl)indole; IT-290, IT-403, U-14,164E, 3-IT[1]
Routes of
administration		Oral, Insufflation, Rectal, Smoked, IM, IV[1]
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1H-Indol-3-yl)propan-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard100.005.522 Edit this at Wikidata
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
  • NC(CC1=CNC2=C1C=CC=C2)C
  • InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3 checkY
  • Key:QSQQQURBVYWZKJ-UHFFFAOYSA-N checkY
  (verify)

αあるふぁ-Methyltryptamine (abbreviated as αあるふぁMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine class.[3][4] It was originally developed as an antidepressant by chemists at Upjohn in the 1960s,[5] and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.[6][7][8]

Chemistry[edit]

αあるふぁMT is a tryptamine with a methyl substituent at the alpha carbon. This alpha substitution makes it a relatively poor substrate for monoamine oxidase A, thereby prolonging αあるふぁMT's half-life, allowing it to reach the brain and enter the central nervous system. Its chemical relation to tryptamine is analogous to that of amphetamine to phenethylamine, amphetamine being αあるふぁ-methylphenethylamine. αあるふぁMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action.

Synthesis[edit]

The synthesis of αあるふぁMT can be accomplished through several different routes, the two most widely known being the Nitroaldol Condensation between Indole-3-carboxaldehyde and nitroethane under ammonium acetate catalysis which produces 1-(3-indolyl)-2-nitropropene-1 which can then be reduced using a reducing agent like lithium aluminum hydride[9] It's also hypothesized to be able to be reduced using Copper(II) chloride and Sodium borohydride, or the condensation between indole-3-acetone and Hydroxylamine [citation needed], followed by reduction of the obtained ketoxime with lithium aluminum hydride.[10]

Pharmacology[edit]

αあるふぁMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine,[11] and as a non-selective serotonin receptor agonist.[12]

MAOI activity[edit]

αあるふぁMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro[13] and in-vivo.[14]

In rats the potency of αあるふぁMT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses.[note 1] Dextroamphetamine did not enhance the 5-hydroxytryptophan-induced rise of serotonin at any level.[15]

Metabolism[edit]

2-Oxo-αあるふぁMT, 6-hydroxy-αあるふぁMT,[16] 7-hydroxy-αあるふぁMT and 1′-hydroxy-αあるふぁMT were detected as metabolites of αあるふぁMT in male Wistar rats .[17]

Dosage and effects[edit]

Under the trade name Indopan, 5-10 milligrams were used for an antidepressant effect.[medical citation needed]

With 20–30 milligrams, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours.[18] A dose exceeding 40 mg is generally considered strong. In rare cases or extreme doses, the duration of effects might exceed 24 hours. Users report that αあるふぁMT in freebase form is smoked, with doses between and 2 and 5 milligrams.[1][unreliable source?][3]

Neurologic side effects of αあるふぁMT include agitation, restlessness, confusion, and lethargy. Physical manifestations including vomiting, mydriasis (pupillary dilation), jaw clenching, tachycardia, salivation, diaphoresis (sweating), and elevations in blood pressure, temperature, and respiratory rate.[19]

Side effects self-reported by recreational users include anxiety, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, as well as psychedelic effects including visual hallucinations and an altered state of mind.[3][20]

Legality[edit]

Australia[edit]

The 5-Methoxy analogue, 5-MeO-αあるふぁMT is schedule 9 in Australia and αあるふぁMT would be controlled as an analogue of this.[21]

China[edit]

As of October 2015 αあるふぁMT is a controlled substance in China.[22]

Denmark[edit]

In Denmark (2010), the Danish Minister for the Interior and Health placed αあるふぁMT to their lists of controlled substances (List B).[23]

Canada[edit]

Canada has no mention of αあるふぁMT in the Controlled Drugs and Substances Act.[24]

Germany[edit]

αあるふぁMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.[23]

Austria[edit]

αあるふぁMT is placed under Austrian law (NPSG) Group 6.[23]

Hungary[edit]

αあるふぁMT was controlled on the Schedule C list in Hungary in 2013.[23]

Slovakia[edit]

αあるふぁMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia.[23]

Slovenia[edit]

αあるふぁMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).[23]

Lithuania[edit]

In Lithuania (2012), αあるふぁMT is controlled as a tryptamine derivative put under control in the 1st list of Narcotic Drugs and Psychotropic Substances which use is prohibited for medical purposes.[23]

Spain[edit]

αあるふぁMT is legal in Spain.[25]

Sweden[edit]

Sveriges riksdags health ministry Statens folkhälsoinstitut classified αあるふぁMT 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 Mar 1, 2005, in their regulation SFS 2005:26 listed as alfa-metyltryptamin (AMT), making it illegal to sell or possess.[26]

United Kingdom[edit]

αあるふぁMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT.[27] This was following the events of 10 June 2014 when the Advisory Council on the Misuse of Drugs recommended that αあるふぁMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.[28]

United States[edit]

The Drug Enforcement Administration (DEA) placed αあるふぁMT temporarily in schedule I of the Controlled Substances Act (CSA) on April 4, 2003, pursuant to the temporary scheduling provisions of the CSA (68 FR16427). On September 29, 2004, αあるふぁMT was permanently controlled as a schedule I substance under the CSA (69FR 58050).[29]

Finland[edit]

AMT, alfa-methyltryptamine is a controlled drug in Finland[30]

Reported deaths[edit]

αあるふぁMT is capable of causing life-threatening side-effects including hyperthermia, hypertension, and tachycardia.[19][31] Fatalities have been reported in association with high doses or concomitant use of other drugs.[32] Fatalities verified with toxicology and autopsy include those of a 22-year-old man in Miami-Dade county and a British teenager, both who died after consuming 1 g of αあるふぁMT.[33][19]

See also[edit]

Notes[edit]

  1. ^ MAOI potency was comparable at 7 μみゅーM/kg, equivalent to 1.5mg/kg of Harmaline and 1.2mg/kg of αあるふぁMT. At 70μみゅーM/kg αあるふぁMT was a much less effective MAOI than harmaline.[15]

References[edit]

  1. ^ a b c "Erowid AMT Vault : FAQ by Dialtonez".
  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. ^ a b c "Erowid Online Books : "TIHKAL" - #48 a-MT".
  4. ^ "Erowid AMT (alpha-methyltryptamine) Vault".
  5. ^ US Patent 3296072, Szmuszkovicz Jacob, "Method of Treating Mental Depression", published 1967-01-03, assigned to Upjohn Co 
  6. ^ Barceloux DG (20 March 2012). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. John Wiley & Sons. pp. 196–. ISBN 978-0-471-72760-6.
  7. ^ Iversen L (11 November 2013). Handbook of Psychopharmacology: Volume 14 Affective Disorders: Drug Actions in Animals and Man. Springer Science & Business Media. pp. 132–. ISBN 978-1-4613-4045-4.
  8. ^ Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders. Academic Press. 17 May 2013. pp. 632–. ISBN 978-0-12-398360-2.
  9. ^ Anonymous. "TheHive". Retrieved 7 June 2023.
  10. ^ Shulgin A. "TIHKAL". Retrieved 18 May 2018.
  11. ^ 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.
  12. ^ Nonaka R, Nagai F, Ogata A, Satoh K (December 2007). "In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes". Biological & Pharmaceutical Bulletin. 30 (12): 2328–2333. doi:10.1248/bpb.30.2328. PMID 18057721.
  13. ^ Arai Y, Toyoshima Y, Kinemuchi H (June 1986). "Studies of monoamine oxidase and semicarbazide-sensitive amine oxidase. II. Inhibition by alpha-methylated substrate-analogue monoamines, alpha-methyltryptamine, alpha-methylbenzylamine and two enantiomers of alpha-methylbenzylamine". Japanese Journal of Pharmacology. 41 (2): 191–197. doi:10.1254/jjp.41.191. PMID 3747266.
  14. ^ Greig ME, Walk RA, Gibbons AJ (October 1959). "The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo". The Journal of Pharmacology and Experimental Therapeutics. 127: 110–115. PMID 13851725.
  15. ^ a b Gey KF, Pletscher A (August 1962). "Effect of alpha-alkylated tryptamine derivatives on 5-hydroxytryptamine metabolism in vivo". British Journal of Pharmacology and Chemotherapy. 19 (1): 161–167. doi:10.1111/j.1476-5381.1962.tb01437.x. PMC 1482243. PMID 13898151.
  16. ^ Szara S (February 1961). "6-Hydroxylation: an important metabolic route for alpha-methyltryptamine". Experientia. 17 (2): 76–77. doi:10.1007/BF02171429. PMID 13774483. S2CID 27030395.
  17. ^ Kanamori T, Kuwayama K, Tsujikawa K, Miyaguchi H, Iwata YT, Inoue H (December 2008). "In vivo metabolism of alpha-methyltryptamine in rats: identification of urinary metabolites". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 38 (12): 1476–1486. doi:10.1080/00498250802491654. PMID 18982537. S2CID 20637936.
  18. ^ Wilcox J (2012). "Psychoactive properties of alpha-methyltryptamine: analysis from self reports of users". Journal of Psychoactive Drugs. 44 (3): 274–276. doi:10.1080/02791072.2012.704592. PMID 23061328. S2CID 38340985.
  19. ^ a b c Boland DM, Andollo W, Hime GW, Hearn WL (July–August 2005). "Fatality due to acute alpha-methyltryptamine intoxication". Journal of Analytical Toxicology. 29 (5): 394–397. doi:10.1093/jat/29.5.394. PMID 16105268.
  20. ^ "Erowid AMT Vault : Effects".
  21. ^ "关于印しるし发《非ひ药用类麻醉ますい药品和わ精神せいしん药品列れつ管かん办法》的てき通知つうち" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  22. ^ a b c d e f g "Reference at www.who.int" (PDF).
  23. ^ "CSDA". Archived from the original on 2011-09-28. Retrieved 2011-06-05.
  24. ^ "Medicamentos de Uso Humano - Estupefacientes y Psicótropos". Agencia Española de Medicamentos y Productos Sanitarios. Archived from the original on 2019-01-02. Retrieved 2019-01-01.
  25. ^ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor;" (PDF), Lagen om förbud mot vissa hälsofarliga varor - SFS 2005:26 (in Swedish), February 2005, archived from the original (PDF) on 2013-09-29, retrieved 2013-10-07
  26. ^ "The Misuse of Drugs (Amendment No. 3) (England, Wales and Scotland) Regulations 2014". www.legislation.gov.uk.
  27. ^ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.
  28. ^ "Alpha-methyltryptamine" (PDF). DEA Office of Diversion Control. April 2013. Archived (PDF) from the original on 2013-10-17. Retrieved 2013-10-10.
  29. ^ "Reference at www.finlex.fi" (PDF).
  30. ^ Gillman PK (October 2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210. PMID 16051647. "drugs such as MDMA, ecstasy (3,4-methylenedioxymethamphetamine), if combined with MAOIs (including moclobemide) do also cause fatalities because they act as serotonin releasers"
  31. ^ "Call for ban on drug after reveller's death". Western Gazette. March 22, 2012. Archived from the original on 2013-10-16. Retrieved October 1, 2013.
  32. ^ "Southampton 'legal high' death deemed 'accidental'". BBC News. 2013-11-12. Retrieved 2013-11-19.

External links[edit]

Retrieved from "https://en.wikipedia.org/w/index.php?title=Αあるふぁ-Methyltryptamine&oldid=1188094928"