DOH-5-hemiFLY

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DOH-5-hemiFLY
Clinical data
Other namesDMA-hemiFly-5; 2,5-DMA-hemiFly-5; Semi-fly; SF
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 1-(5-methoxy-2,3-dihydro-1-benzofuran-4-yl)propan-2-amine
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC12H17NO2
Molar mass207.273 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C=CC2=C1CCO2)OC)N
  • InChI=1S/C12H17NO2/c1-8(13)7-10-9-5-6-15-12(9)4-3-11(10)14-2/h3-4,8H,5-7,13H2,1-2H3
  • Key:XDJBFAKEKIPGDT-UHFFFAOYSA-N

DOH-5-hemiFLY, or DMA-hemiFly-5, also known as semi-fly (SF), is a serotonin receptor modulator and putative psychedelic drug of the phenethylamine, amphetamine, DOx, and benzofuran families related to 2,5-dimethoxyamphetamine (2,5-DMA; DOH).[1][2][3][4][5] It is a cyclized derivative of 2,5-DMA related to the FLY psychedelics.[1][4][5] The drug shows affinity for the serotonin 5-HT2A receptor (Ki = 146 nM) and fully substitutes for LSD in rodent drug discrimination tests, albeit with relatively low potency.[1][4][5] The chemical synthesis of DOH-5-hemiFLY has been described.[5] DOH-5-hemiFLY was first described in the scientific literature by David E. Nichols and colleagues in 1991.[1][5]

See also

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References

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  1. ^ a b c d Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 495–497, 503, 670–671, 851–852, 860. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  2. ^ Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  3. ^ Nichols DE (1994). "Medicinal Chemistry and Structure–Activity Relationships". In Cho AK, Segal DS (eds.). Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. pp. 3–41. ISBN 978-0-12-173375-9. Researchers have suggested that this moiety may force the 5-methoxy group to adopt an "anti" orientation (Nichols et al., 1986b). For example, the 2,3-dihydrobenzofuran-6-yl compounds 31 and 32 have been shown to lack LSD-like activity, whereas the dihydrobenzofuran-4-yl compound 33 is as potent as its flexible 5-methoxy analog DOB (Table l; Nichols et al., 1991 c). These studies clearly show that the preferred orientation of the 5-methoxy group is anti with respect to the 4 substituent.
  4. ^ a b c Blaazer AR, Smid P, Kruse CG (September 2008). "Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors". ChemMedChem. 3 (9): 1299–1309. doi:10.1002/cmdc.200800133. PMID 18666267. Orienting the oxygen lone pair anti to the side chain gave compound 35 and the 7-bromo analogue 36. [184] DD tests showed full substitution for both compounds in rats trained to discriminate LSD from saline, with the 7-bromo analogue 36 (ED50=0.57 mmol kg/1 ) more potent than DOM (15, ED50= 0.89 mmol kg/1 ) and equipotent to DOB (16). Binding affinity and energy calculations confirmed that these rigid analogues model the active binding conformation of DOM (15).[184]
  5. ^ a b c d e Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". Journal of Medicinal Chemistry. 34 (1): 276–281. doi:10.1021/jm00105a043. PMID 1992127.
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