Hemi-flyscaline

Hemi-flyscaline
Clinical data
Other namesHemi-Mescaline-FLY; HMesFLY; 3-Dihydrofuranmescaline; 3-DHFMescaline; 3-DHF-M; Mescaline-HemiFLY; M-HemiFLY; FM; MeO-2C-ISF
Drug classserotonin receptor modulator; putative non-hallucinogenic 5-HT2A receptor agonist
Identifiers
  • 2-(6,7-dimethoxy-2,3-dihydro-1-benzofuran-4-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H17NO3
Molar mass223.272 g·mol−1
3D model (JSmol)
  • COC1=C(C2=C(CCO2)C(=C1)CCN)OC
  • InChI=InChI=1S/C12H17NO3/c1-14-10-7-8(3-5-13)9-4-6-16-11(9)12(10)15-2/h7H,3-6,13H2,1-2H3
  • Key:GGGQVCBWGWDHMQ-UHFFFAOYSA-N

Hemi-flyscaline (Hemi-Mescaline-FLY or HMesFLY), also known as 3-dihydrofuranmescaline (3-DHFMescaline; 3-DHF-M), it is also known by other names, including Mescaline-HemiFLY (M-HemiFLY), and also by the abbreviation FM. It is a putative non-hallucinogenic agent and, primarily, a serotonin receptor modulator.[1][2] This compound belongs to the phenethylamine family and is only partially related to scaline and FLY due to the altered structure of the second furan ring and the presence of two methoxy substituents at the 6 and 7 positions.

Pharmacology

Pharmacodynamics

Several studies have been conducted to assess the serotonergic activity of hemi-flyscaline; one such study, carried out in 1999 on rats, showed that it had a moderate affinity for the serotonin 5-HT2A receptor, with an inhibition constant (Ki) of 130 nM,[1] In another behavioural study by David E. Nichols in 2012, also conducted on animals, he noted a "complete loss of efficacy" as well as a ‘loss of mescaline-like potency’, although he made this observation whilst comparing it on an equal footing with other potent hallucinogens;[2] however, in his subsequent 2017 study examining the efficacy of hallucinogens, he concluded that hemi-flyscaline exhibits a very high affinity (with a Ki value of 6.3 nM) for the serotonin 5-HT2A receptor but does not induce behavioural effects.[3]

Chemistry

It looks like shiny white crystals.[4]

Synthesis

It is synthesised from 2,3,4-trimethoxybenzoic acid by its cyclisation to a 6,7-dimethoxybenzofuran-3-one intermediate, followed by hydrogenation, selective demethylation, the introduction of a cyanomethyl group via the Mannich reaction, re-methylation and final catalytic reduction of the nitrile to an aminoethyl chain.[4]

History

Hemi-flyscaline was first described in the scientific literature by David E. Nichols and colleagues in 1995.[5]

See also

References

  1. 1 2 Schulze-Alexandru M, Kovar KA, Vedani A (1999). "Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances". Quantitative Structure-Activity Relationships. 18 (6): 548–560. doi:10.1002/(sici)1521-3838(199912)18:6<548::aid-qsar548>3.3.co;2-2. ISSN 0931-8771.
  2. 1 2 Nichols DE (2012-02-28). "Structure–activity relationships of serotonin 5-HT2Aagonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X.
  3. ↑ Nichols DE (2017). "Chemistry and Structure–Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 1–43. ISBN 978-3-662-55878-2.
  4. 1 2 Monte AP, Waldman SR, Marona-Lewicka D, Wainscott DB, Nelson DL, Sanders-Bush E, et al. (September 1997). "Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives". Journal of Medicinal Chemistry. 40 (19): 2997–3008. doi:10.1021/jm970219x. PMID 9301661.
  5. ↑ Monte AP (August 1995). Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines (Ph.D. thesis). Purdue University.
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