Bromo-dragonfly

Bromo-DragonFLY

Names
IUPAC name 1-(4-Bromofuro[2,3-f] [1]benzofuran-8-yl)propan-2-amine
Other names Bromo-benzodifuranyl-isopropylamine
Identifiers
CAS Number	502759-67-3 N
3D model (Jmol)	Interactive image Interactive image
ChEMBL	ChEMBL149024 N
ChemSpider	8014776 N 8719838 R N 8672089 S N
PubChem	9839057 10544447 R 10496688 S
InChI InChI=1S/C13H12BrNO2/c1-7(15)6-10-8-2-4-17-13(8)11(14)9-3-5-16-12(9)10/h2-5,7H,6,15H2,1H3 N Key: GIKPTWKWYXCBEC-UHFFFAOYSA-N N
SMILES CC(N)Cc1c2ccoc2c(Br)c2ccoc12 CC(N)CC1=C2OC=CC2=C(Br)C2=C1C=CO2
Properties
Chemical formula	C 13H 12BrNO 2
Molar mass	294.144 g mol−1
log P	2.519
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Bromo-DragonFLY (or 3C-Bromo-Dragonfly, DOB-Dragonfly) is a psychedelic drug related to the phenethylamine family. Bromo-DragonFLY is considered an extremely potent hallucinogen, around one third as potent as LSD with a normal dose in the region of 200 μg to 800 μg, and it has an extremely long duration of action, up to several days. Bromo-DragonFLY has a stereocenter and R-(−)-bromo-DragonFLY is the more active stereoisomer.

Bromo-DragonFLY was first synthesized by Matthew Parker in the laboratory of David E. Nichols in 1998. As with the earlier and less potent dihydrofuran series of compounds nicknamed FLY, Bromo-DragonFLY was named after its superficial structural resemblance to a dragonfly.

The hallucinogenic effect of bromo-DragonFLY is mediated by its agonist activity at the 5-HT_2A serotonin receptor. Bromo-DragonFLY also has a high binding affinity for the 5-HT_2B and 5-HT_2Cserotonin receptors, and is most accurately described as a non-subtype selective 5-HT₂ agonist, as it is actually twice as potent an agonist for 5-HT_2C receptors as for 5-HT_2A, as well as being less than 5x selective for 5-HT_2A over 5-HT_2B.

The typical dose of Bromo-DragonFLY is not known, however it has varied from 500 μg to 1 mg. It has about 300 times the potency of mescaline, or 1/5 the potency of LSD. It has been sold in the form of blotters, similar to the distribution method of LSD, which has led to confusion, and reports of mistakenly consuming Bromo-DragonFly. It has a much longer duration of action than LSD and can last for up to 2–3 days following a single large dose, with a slow onset of action that can take up to 6 hours before the effects are felt.