2,5-Dimethoxy-4-bromoamphetamine

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2,5-Dimethoxy-4-bromoamphetamine (DOB), also known as brolamfetamine (INNTooltip International Nonproprietary Name), is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. For many years, prior to the discovery of newer compounds, DOB was the most potent known phenethylamine psychedelic. It is taken orally.

The drug acts as an agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A receptor. Analogues of DOB include 2C-B, DOM, DOI, and Bromo-DragonFLY (DOB-DFLY), among others.

DOB was first synthesized by Alexander Shulgin in 1967 and was described by him and his colleagues in the scientific literature in 1971. Shulgin subsequently further described the effects of DOB in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

Use and effects

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

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. At a low dose of 0.4mg DOB, there was only enhanced visual perception, strengthening of colors, enriched emotional affect, a comfortable good feeling, and colorful and important dreams.

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

Side effects

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

Overdose

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

Interactions

DOB may interact synergistically with alcohol.

Pharmacology

Pharmacodynamics

DOB activities

Target	Affinity (Ki, nM)
5-HT1A	2,550–7,904
5-HT1B	941
5-HT1D	636
5-HT1E	556–1,427
5-HT1F	ND
5-HT2A	0.6–81 (Ki) 0.52–50 (EC50Tooltip half-maximal effective concentration) 57–105% (EmaxTooltip maximal efficacy)
5-HT2B	2.9–44 (Ki) 2.82–65 (EC50) 70–100% (Emax)
5-HT2C	1.3–78 (Ki) 0.25–102 (EC50) 58–112% (Emax)
5-HT3	>10,000
5-HT4	ND
5-HT5A	5,311
5-HT6	5,535
5-HT7	506
α1A, α1B	>10,000
α1D	ND
α2A	4,266
α2B	1,527
α2C	594
β1	2,425
β2	303
D1, D2	>10,000
D3	808
D4, D5	>10,000
H1	9,120
H2–H4	>10,000
M1, M2	>10,000
M3	1,152
M4, M5	>10,000
TAAR1	>1,000
I1	1,596
σ1	2,193
σ2	>10,000
SERTTooltip Serotonin transporter	8,538 (Ki)
NETTooltip Norepinephrine transporter	>10,000 (Ki)
DATTooltip Dopamine transporter	>10,000 (Ki)
MAO-ATooltip Monoamine oxidase A	100,000 (IC50Tooltip half-maximal inhibitory concentration) (rat)
MAO-BTooltip Monoamine oxidase B	>100,000 (IC50) (rat)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:

DOB is a serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor agonist. Its psychedelic effects are mediated by its agonistic properties at the 5-HT_2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT₂ receptor subfamily.

It is a very weak agonist of the human trace amine-associated receptor 1 (TAAR1) and a weak agonist of the rhesus monkey TAAR1. In contrast to the serotonin releasing agent MDMA, DOB does not produce protein kinase C (PKC) activation in the brains of rodents in vivo. The PKC activation by MDMA appears to be dependent on uptake by the serotonin transporter (SERT).

DOB has been found to reduce aggression in rats.

DOB is one of the most potent compounds in PiHKAL; while the active dose is similar to that of DOI, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by serotonin 5-HT₂ receptors.

Chemistry

File:DOB blotters.jpg

Tabs of DOB, confiscated by police in Concord, California in 2006.

The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. 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.

Synthesis

The chemical synthesis of DOB has been described.

Analogues

Omission of the amphetamine related α-methyl leads to 2C-B, a compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist. Other analogues of DOB include 4C-B, Bromo-DragonFLY, DOB-FLY, DOB-5-hemiFLY, and 25B-NBOMe, among others.

History

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

Society and culture

Legal status

Internationally, DOB is a Schedule I substance under the Convention on Psychotropic Substances and the drug is legal only for medical, industrial or scientific purposes.

Canada

Listed as a Schedule 1 as it is an analogue of amphetamine.

Australia

DOB is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017). A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.

Russia

Schedule I, possession of at least 10 mg is a criminal offence.

United Kingdom

DOB is a Class A drug in the United Kingdom under the Misuse of Drugs Act 1971.

United States

DOB is a Schedule I controlled substance under federal law in the United States. It was scheduled in 1973.

See also

• DOx (psychedelics)

External links

• DOB - Isomer Design
• DOB - PsychonautWiki
• DOB - Erowid
• DOB - TripSit
• The Big & Dandy DOB Thread - Bluelight
• DOB - PiHKAL - Erowid
• DOB - PiHKAL - Isomer Design