2,5-Dimethoxy-4-bromoamphetamine

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DOB's dose as 1 to 3 mg orally and its duration as 18 to 30 hours.^[1] In an earlier publication, he listed its dose as 2 to 3 mg for racemic DOB and 1 to 2 mg for the preferentially active (R)-DOB enantiomer.^[1] In addition, he described the duration as being extremely long, with a gradual descent and baseline being achieved after 24 to 36 hours.^[2][1] The onset has been described as 1 to 2 hours, the time to peak as 3 or 4 hours, and a plateau occurring from 4 to 10 hours.^[1][2] Its onset is said to be relatively slow.^[1]

The effects of DOB and (R)-DOB have been reported to include visual changes such as prismatic-colored rings around the moon and long-lasting "after-images" following seeing points of light, little visual distortion, an "incredible Moebius strip representation of reality at the intellectual level", rich fantasy, flashes of depersonalization, cosmic thinking, introspection, insights, intoxication, impairment, stimulation, brief lapses in attention or "little fugue states", body load, cramps, muscle tremors, and sleep disruption.^[1][2] At a low dose of 0.4 mg DOB, there was only enhanced visual perception, strengthening of colors, enriched emotional affect, a comfortable good feeling, and colorful and important dreams.^[1]

(R)-DOB produced moderate effects at a dose of 0.5 mg and pronounced effects at 1.0 to 1.5 mg, whereas there were no effects with 0.5 mg (S)-DOB and only threshold and very slight effects with 1.0 mg (S)-DOB.^[1] In relation to this, (R)-DOB is described as the more active enantiomer and (S)-DOB as much less active.^[1] In one report, 1 mg (R)-DOB was described as not as strong as 2 mg DOB, suggesting that it is more potent than the racemate but is not double its potency and hence that (S)-DOB also contributes to the effects of the racemate.^[1] (S)-DOB has never been tested up to fully active doses.^[1] In another source however, by Richard Glennon and colleagues, the approximate hallucinogenic dose was listed as 0.8 to 2.0 mg for racemic DOB, 0.5 mg for (R)-DOB, and 5.0 mg for (S)-DOB.^[9]

Side effects of DOB include body load, muscle tremors, muscle cramps, attention lapses described as "little fugue states", sleeping difficulties, and bizarre dreams.^[1][2]

Overdose of DOB has been reported to produce cardiovascular symptoms and convulsions.^[2] Excessively high doses of DOB may cause diffuse arterial spasm.^[10] The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline.^[10] A 35 mg overdose resulted in death, while a 75 mg overdose in a person with tolerance resulted in ergotism-like complications that required amputation.^[2]

DOB may interact synergistically with alcohol.^[2]

The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine.^[1] DOB has a stereocenter and R-(−)-DOB is the eutomer. This is an important finding as it is suggestive that it is targeting different receptors relative to most other phenethylamines (e.g. MDMA) where the R-isomer serves as the distomer.

DOB was first synthesized by Alexander Shulgin in 1967.^[1] It was first described in the scientific literature in a paper by Shulgin, Claudio Naranjo, and another colleague in 1971.^[8] The INNTooltip International Nonproprietary Name of DOB, brolamfetamine, was proposed and recommended by the World Health Organization (WHO) in 1986.^[25][26] This was the same year that the Multidisciplinary Association for Psychedelic Studies (MAPS) was founded.^[27] DOB was registered with the WHO as a supposed "anorexic" (appetite suppressant).^[28]

• DOx (psychedelics)