Mescaline-FLY

Mescaline-FLY, also known as flyscaline, M-FLY, or MeO-2C-2,6-IFLY, is a putatively non-hallucinogenic serotonin receptor modulator of the phenethylamine, scaline, and FLY families.^[1][2][3][4] It is the FLY (benzodifuran) analogue of the psychedelic drug mescaline.^[1][2][3][4]

Mescaline-FLY

Clinical data
Other names	Flyscaline; M-FLY; MeO-2C-2,6-IFLY; BAT; 3,5-DHF-Mescaline; 3,5-Dihydrofuran-mescaline
Drug class	Serotonin receptor modulator; Non-hallucinogenic serotonin 5-HT2A receptor agonist
ATC code	None
Identifiers
IUPAC name 2-(8-methoxy-2,3,5,6-tetrahydrofuro[3,2-f][1]benzofuran-4-yl)ethanamine
CAS Number	194787-78-5
PubChem CID	10609802
ChemSpider	8785169
ChEMBL	ChEMBL316527
Chemical and physical data
Formula	C13H17NO3
Molar mass	235.283 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=C2C(=C(C3=C1OCC3)CCN)CCO2
InChI InChI=1S/C13H17NO3/c1-15-13-11-9(3-6-16-11)8(2-5-14)10-4-7-17-12(10)13/h2-7,14H2,1H3 Key:NZPLNCQAEYLYII-UHFFFAOYSA-N

Pharmacology

Mescaline-FLY shows affinity for the serotonin 5-HT₂ receptors.^[3] Its affinities (K_i) were 335 to 4,443 nM for the serotonin 5-HT_2A receptor, 205 to 302 nM for the serotonin 5-HT_2B receptor, and 61.5 to 654 nM for the serotonin 5-HT_2C receptor.^[3] The affinity of mescaline-FLY for the serotonin 5-HT_2A receptor was only slightly higher than that of mescaline, whereas it showed several-fold higher affinity for the serotonin 5-HT_2C receptor and about 2-fold higher affinity for the serotonin 5-HT_2B receptor compared to mescaline.^[3] In a subsequent study, at the serotonin 5-HT_2A receptor, its affinity (K_0.5) was 243 nM and its EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy) was 3,470 nM (57%), relative to respective values for mescaline of 801 nM and 2,700 nM (88%).^[5] Hence, whereas mescaline is a full agonist of the serotonin 5-HT_2A receptor, mescaline-FLY is a moderate-efficacy partial agonist of the receptor.^[5]

The drug failed to substitute for LSD in rodent drug discrimination tests, producing a maximum substitution of 29% at a dose of 55.2 μmol/kg, whereas mescaline fully substituted for LSD with an ED₅₀Tooltip median effective dose of 33.5 μmol/kg.^{[3][4][6][7][8]} The lack of substitution with mescaline-FLY is in notable contrast to findings with other FLY drugs, such as 2C-B-FLY, DOB-FLY, and Bromo-DragonFLY.^[6][7][8][9] Mescaline-FLY is not known to have been tested in humans, and hence it is unknown whether it produces psychedelic effects in humans.^[1] However, based on its lack of psychedelic-like effects in rodent drug discrimination tests, it may not be expected to be hallucinogenic in humans.^[3][4]

History

Mescaline-FLY was first described in the scientific literature by the lab of David E. Nichols and colleagues by 1995.^[3][4]

See also

• Substituted methoxyphenethylamine
• FLY (psychedelics)
• Substituted mescaline analogue
• NBOMe-mescaline