2C-B-5-hemiFLY-α6

2C-B-5-hemiFLY-α6, also known as BNAP, is a serotonin receptor modulator of the phenethylamine and FLY families related to the psychedelic drugs 2C-B and DOB.^[1][2][3] It is a cyclized phenethylamine with a partial ergoline- or LSD-like chemical structure.^[1][2][3] Its tricyclic structure mimics the A, B, and C rings of LSD.^[2][1]

2C-B-5-hemiFLY-α6

Clinical data
Other names	BNAP
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name 8-bromo-6-methoxy-2a,3,4,5-tetrahydro-2H-naphtho[1,8-bc]furan-4-amine
ChemSpider	21376194
Chemical and physical data
Formula	C12H14BrNO2
Molar mass	284.153 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1cc(Br)c2c3c1CC(N)CC3CO2
InChI InChI=1S/C12H14BrNO2/c1-15-10-4-9(13)12-11-6(5-16-12)2-7(14)3-8(10)11/h4,6-7H,2-3,5,14H2,1H3 Key:CLZKGXPLDDUCQZ-UHFFFAOYSA-N

Pharmacology

The more active syn stereoisomer of the drug shows high affinity for the human serotonin 5-HT_2A and 5-HT_2C receptors with agonist radioligands (K_i = 13–16 nM and 4–6 nM, respectively).^[2][1][4][5] These affinities were 20- to 30-fold lower than those of the related drug DOB-FLY.^[2][4] The stereoisomer also showed much weaker affinity for the serotonin 5-HT_2B receptor with agonist radioligand (K_i = 280 nM) and for the serotonin 5-HT_1A receptor (K_i = 960 nM).^[4][5] Affinities for rat serotonin receptors and for human serotonin receptors with antagonist radioligands were much lower.^[3] A subsequent study showed the more active enantiomer to be a partial agonist of the rat serotonin 5-HT_2A receptor (EC₅₀Tooltip half-maximal effective concentration = 2,090 nM; E_maxTooltip maximal efficacy = 63%).^[6][5] Neither stereoisomer produced LSD-like effects in rodent drug discrimination tests.^[2][1][3] Unexpectedly, the more active stereoisomer showed relatively high affinity for the five muscarinic acetylcholine receptors (K_i = 12–81 nM).^[1][4][3]

History

2C-B-F-hemiFLY-α6 was first described in the scientific literature by 1995.^[4][3] The compound resulted in conclusions that phenethylamines and lysergamides do not necessarily interact with the serotonin 5-HT_2A receptor in the same manner.^[1][2] Following the negative findings, further investigation in this area was discontinued.^[2]

Analogues

Analogue of 2C-B-5-hemiFLY-α6 with the amine modified showed not only high-affinity partial agonism at the serotonin 5-HT_2A receptor but also partially substituted for LSD and DOI in rodent drug discrimination tests.^[2][5]

See also

• Substituted methoxyphenethylamine
• FLY
• Partial ergoline
• RU-27849
• FHATHBIN