DOB-5-hemiFLY

Last updated

DOB-5-hemiFLY
DOB-HEMIFLY-5 structure.png
Clinical data
Other namesBromo-semi-fly; B-Semi-fly; B-SF; 5-MeO-7-Br-4-APDB; 7-Bromo-2,3-dihydro-5-methoxy-α-methyl-4-benzofuranethanamine; F-4A5,7B; DOB-5-HEMIFLY
Drug class Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 1-(7-bromo-5-methoxy-2,3-dihydro-1-benzofuran-4-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C12H16BrNO2
Molar mass 286.169 g·mol−1
3D model (JSmol)
  • CC(CC1=C2CCOC2=C(C=C1OC)Br)N
  • InChI=1S/C12H16BrNO2/c1-7(14)5-9-8-3-4-16-12(8)10(13)6-11(9)15-2/h6-7H,3-5,14H2,1-2H3
  • Key:PKJQSBXFDIUPBW-UHFFFAOYSA-N

DOB-5-hemiFLY, also known as bromo-semi-fly (B-SF) or as 5-MeO-7-Br-4-APDB, is a putative serotonergic psychedelic of the phenethylamine, amphetamine, DOx, and benzofuran families related to DOB and DOB-FLY. [1] [2] It is the derivative of DOB in which the methoxy group at the 5 position has been cyclized with the benzene ring to form a dihydrofuran group or benzodihydrofuran ring system. [1] [2] The drug differs from the FLY psychedelics DOB-FLY and Bromo-DragonFLY (DOB-DFLY) in that only one of the methoxy groups has been cyclized rather than both. [1] [2]

Contents

Use and effects

The properties and effects of DOB-5-hemiFLY in humans are unknown. [1]

Interactions

Pharmacology

Pharmacodynamics

DOB-5-hemiFLY shows high affinity for the serotonin 5-HT2 receptors, including for the 5-HT2A receptor (Ki = 3.1 nM). [1] [2] [3] [4] [5] [6] Its affinity for this receptor is similar to that of DOB. [5] [6] The drug fully substitutes for LSD in rodent drug discrimination tests and shows high potency in this regard, with potency similar to that of DOB as well. [1] [2] [7] [3] [4] [5] [8] [6] [ excessive citations ]

Chemistry

Synthesis

The chemical synthesis of DOB-5-hemiFLY has been described. [1] [5]

Derivatives

Derivatives of DOB-5-hemiFLY include DOB-FLY and Bromo-DragonFLY (DOB-DFLY). [1] [2]

History

DOB-5-hemiFLY was first described in the scientific literature by David E. Nichols and colleagues in 1991. [1] [2] [5] It was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . [1]

Society and culture

United States

DOB-5-hemiFLY is not an explicitly controlled substance in the United States as of 2011. [1] [ needs update ]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 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.
  2. 1 2 3 4 5 6 7 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. 496–497, 851–852, 860. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  3. 1 2 Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT 2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN   2190-460X . Retrieved 26 November 2025. When the 5-methoxy of DOM (39) was 'tethered' to the 4-position, as in 47, the activity was reduced nearly 20-fold compared to DOM in drug discrimination tasks.81 By contrast, when the 5-methoxy was tethered to the 6-position, compound 48 was as at least as potent as DOM.82 These studies seemed to indicate clearly that the electrons of the methoxy oxygen should be oriented in a particular direction for optimal receptor interaction. Affinity for the [125I]DOI-labeled receptor in rat prefrontal cortex paralleled these findings, with an affinity for 47 of 488 nM and for 48 of 3.1 nM (Figure 20).
  4. 1 2 Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. 36: 1–43. doi:10.1007/7854_2017_475. ISBN   978-3-662-55878-2. PMID   28401524. "Tethering" the 5-methoxy of DOM (37) to the 4-position, leading to compound 49, reduced activity nearly 20-fold in an in vivo rat drug discrimination assay, compared to DOM. (Nichols et al. 1986) When the 5-methoxy of DOB was tethered to the 6-position, however, compound 50 was as potent as DOM (Nichols et al. 1991). Affinity at the [125I]DOI-labeled 5HT2A receptor in rat prefrontal cortex was consistent with the in vivo findings, where the affinity of 49 was 488 nM and 50 was 3.1 nM. These results were consistent with the hypothesis that the oxygen electrons needed to project in a specific direction for proper receptor interaction.
  5. 1 2 3 4 5 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.
  6. 1 2 3 Monte AP, Marona-Lewicka D, Parker MA, Wainscott DB, Nelson DL, Nichols DE (July 1996). "Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups". Journal of Medicinal Chemistry. 39 (15): 2953–2961. doi:10.1021/jm960199j. PMID   8709129.
  7. ↑ 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]
  8. ↑ 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 beeen 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 wich respect to the 4 substituent.
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