Substituted alpha-alkyltryptamine

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α-Alkyltryptamines are a group of substituted tryptamines which possess an alkyl group, such as a methyl or ethyl group, attached at the alpha carbon.[1][2][3] α-Alkylation of tryptamine makes it much more metabolically stable and resistant to degradation by monoamine oxidase, resulting in increased potency and greatly lengthened half-life.[3] This is analogous to α-methylation of phenethylamine into amphetamine.[3]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[4][5][6][7] and produce psychostimulant, entactogen, and/or psychedelic effects.[1][2][3] The most well-known of these agents are α-methyltryptamine (αMT) and α-ethyltryptamine (αET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs.[2][3] In accordance with its action as a dual releasing agent of serotonin and dopamine, αET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as αMT, 5-MeO-αMT, and various others.[8]

List of substituted α-alkyltryptamines[edit]

Structure Common name Chemical name CAS number
AMT.svg αMT 1-(1H-Indol-3-yl)propan-2-amine 299-26-3
4-hydroxy-alphamethyltryptamine.png 4-HO-αMT 3-(2-aminopropyl)-1H-indol-4-ol 15066-09-8
4-Methyl-AMT.png 4-Methyl-αMT 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine 3569-29-7
5-fluoro-alpha-methyltryptamine.svg 5-Fluoro-αMT 1-(5-fluoro-1H-indol-3-yl)propan-2-amine 712-08-3
5-Chloro-3-(2-aminopropyl)indole.svg 5-Chloro-αMT 1-(5-Chloro-1H-indol-3-yl)propan-2-amine 712-07-2
5-HO-AMT structure.png 5-HO-αMT (αMS/α-methyl-5-HT) 3-(2-aminopropyl)-1H-indol-5-ol 304-52-9
5-MeO-AMT.svg 5-MeO-αMT 1-(5-methoxy-1H-indol-3-yl)propan-2-amine 1137-04-8
5EtO-AMT structure.png 5-Ethoxy-αMT 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine 101832-83-1
6-fluoro-AMT structure.png 6-Fluoro-αMT 1-(6-fluoro-1H-indol-3-yl)propan-2-amine 712-11-8
A,N,O-TMS.png N-Methyl-5-MeO-αMT (α,N,O-TMS/α,N,O-trimethyl-5-HT) [1-(5-methoxy-1H-indol-3-yl)propan-2-yl](methyl)amine 4822-13-3
Α,N,N-TMT.png N,N-Dimethyl-αMT (α,N,N-TMT) (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine
5MeO-TMT structure.png N,N-Dimethyl-5-MeO-αMT (5-MeO-α,N,N-TMT) (2-(5-methoxy-1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine 101831-90-7
AMDIPT structure.png αMDiPT (2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
BW-723C86 structure.png BW-723C86 1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine 160521-72-2
AL-37350A structure.png AL-37350A (4,5-dihydropyrano-αMT) (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole 362603-40-5
AET.svg αET 1-(1H-indol-3-yl)butan-2-amine 2235-90-7
4-Methyl-AET.png 4-Methyl-αET 1-(4-Methyl-1H-indol-3-yl)butan-2-amine 28289-30-7
4HO-AET structure.png 4-HO-αET 1-(4-hydroxy-1H-indol-3-yl)butan-2-amine 28289-28-3
5F-AET structure.png 5-Fluoro-αET 1-(5-fluoro-1H-indol-3-yl)butan-2-amine 1380137-98-3
5Me-AET structure.png 5-Methyl-αET 1-(5-methyl-1H-indol-3-yl)butan-2-amine 1380148-21-9
5-MeO-AET.svg 5-MeO-αET 1-(5-methoxy-1H-indol-3-yl)butan-2-amine 4765-10-0
7-Methyl-AET.png 7-Methyl-αET 1-(7-methyl-1H-indol-3-yl)butan-2-amine 13712-80-6
MPMI structure.png MPMI 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole 143321-54-4
4-HO-N-Me-TMT.png Lucigenol (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole 250672-65-2
5-MeO-N-Me-TMT.svg 5-MeO-MPMI 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole 143321-57-7
5F-MPMI structure.png 5-F-MPMI 5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole
5Br-MPMI structure.png 5-Br-MPMI 5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole 143322-57-0
Eletriptan skeletal.svg Eletriptan 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole 143322-58-1

See also[edit]

References[edit]

  1. ^ a b Richard K. Ries; Shannon C. Miller; David A. Fiellin (2009). Principles of Addiction Medicine. Lippincott Williams & Wilkins. pp. 216–218. ISBN 978-0-7817-7477-2.
  2. ^ a b c Richard R. Laing (2003). Hallucinogens: A Forensic Drug Handbook. Academic Press. pp. 102–. ISBN 978-0-12-433951-4.
  3. ^ a b c d e Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 641–. ISBN 978-1-60913-345-0.
  4. ^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur. J. Pharmacol. 559 (2–3): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  5. ^ Blough BE, Landavazo A, Partilla JS, et al. (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–8. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
  6. ^ 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): 2328–33. doi:10.1248/bpb.30.2328. PMID 18057721.
  7. ^ Feldman JM, Chapman B (December 1975). "Monoamine oxidase inhibitors: nature of their interaction with rabbit pancreatic islets to alter insulin secretion". Diabetologia. 11 (6): 487–94. doi:10.1007/bf01222097. PMID 1107123.
  8. ^ Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology. 200 (1): 187–190. doi:10.1016/0014-2999(91)90686-K. PMID 1722753.

Further reading[edit]