FLY (psychedelics)

Not to be confused with FLY (psychedelic).

FLY is a family of phenethylamine and benzofuran psychedelics possessing a benzodifuran or similar ring system.^{[1][2][3][4][5]} The FLY drugs were so-named because of the resemblance of their chemical structures to flying insects like dragonflies and butterflies.^[1][2][3][5] They are analogues of 2,5-dimethoxyphenethylamines in which the 2- and 5-position methoxy groups have been cyclized into furan and/or tetrahydrofuran rings.^[1][2][3] They may be 2C, DOx, 25-NB, or other FLY versions of psychedelic phenethylamines.^[1][2]

2C-B-FLY, an example of a FLY psychedelic.

2C-B-DRAGONFLY, an example of a DragonFLY psychedelic.

2C-B-BUTTERFLY, an example of a ButterFLY psychedelic.

Examples of different FLY drugs.

Examples of different types of FLY drugs, in the case of the base psychedelic 2C-B, include 2C-B-FLY, 2C-B-DRAGONFLY, and 2C-B-BUTTERFLY, among others.^[1][2][6] BromoDragonFLY (DOB-DragonFLY) is known for its very high potency and its toxicity in overdose.^[5][7][3] 2C-B-FLY was Ann Shulgin's favorite psychedelic.^{[8][9][10][11]}

Several of the FLY drugs have been shown to act as potent serotonin 5-HT₂ receptor agonists.^[12][13][14]

Use and effects

According to Alexander Shulgin, active doses or dose ranges of FLY drugs are 2.5 to 10 mg orally for 2C-B-FLY, 1 mg orally for DOB-FLY, and 100 μg intramuscularly for Bromo-DragonFLY.^[2][15] Other sources provide dose ranges of 0.2 to 0.8 mg orally for Bromo-DragonFLY, 1 mg orally for DOB-FLY, and 10 to 20 mg for 2C-B-FLY.^[16][6][5]

Oral doses and durations of FLY psychedelics

Compound	Dose	Duration
2C-B-FLY	2.5–10 mg or 10–20 mg (2–25 mg+)	Unknown
DOB-FLY	1 mg	Unknown
Bromo-DragonFLY	0.2–0.8 mg (0.2–1 mg+)	12–24 hoursa
Footnotes: a Bromo-DragonFLY can have a delayed onset of up to 6 hours and can have a duration of up to 2 to 3 days in some cases. Refs: [4][16][15][2] Individual: [6][7][17][18][19][5]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

History

The FLY drugs were first described in the scientific literature by Aaron Phillip Monte and David E. Nichols and colleagues at Purdue University by 1995.^[20][21]

List of FLY drugs

See also: Substituted benzofuran § List of substituted benzofurans

2C FLY drugs

• 2C-B-FLY
• 2C-B-BUTTERFLY (2C-B-MOTH)
• 2C-B-DRAGONFLY
• 2CB-5-hemifly
• 2C-C-FLY
• 2C-I-FLY
• 2C-D-FLY
• 2C-E-FLY
• 2C-EF-FLY
• 2C-T-7-FLY

DOx FLY drugs

• Bromo-DragonFLY (DOB-Dragonfly; DOB-DFLY)
• DOB-FLY (3C-B-FLY)
• DOB-2-DRAGONFLY-5-BUTTERFLY
• DOB-5-HEMIFLY (bromo-semi-FLY; B-SF)
• DOB-butterFLY (DOB-MOTH)
• DOH-5-hemiFLY (semi-FLY; SF)
• DOI-2-HEMIFLY
• DOM-FLY
• DOMOM-FLY
• DragonFLY (DFLY)
• FLY (DOH-FLY)
• TFMFly

25-NB FLY drugs

• 2C-B-Fly-NBOMe (NBOMe-2CB-Fly)
• 2C-B-DragonFLY-NBOH
• 2C-B-FLY-NB2EtO5Cl

Other FLY drugs

• Mescaline-FLY (flyscaline)

See also

• Substituted phenethylamine
• Substituted amphetamine
• Substituted benzofuran
• Substituted methoxyphenethylamine
• 2C, DOx, 4C, 25-NB
• Substituted mescaline analogue, 3C
• PiHKAL (Phenethylamines I Have Known and Loved)
• The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds
• 2C-B-5-hemiFLY-α6
• F (psychedelic)