2,5-Dimethoxy-4-bromoamphetamine

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| _other_data=1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine

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2,5-Dimethoxy-4-bromoamphetamine (DOB), also known as brolamfetamine (Template:Abbrlink),<ref name="Organization2000">Template:Cite book</ref> is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.<ref name="Shulgin1981">Template:Cite journal</ref> For many years, prior to the discovery of newer agents such as DOTFM, FLY compounds like Bromo-DragonFLY, and NBOMe compounds like 25I-NBOMe, DOB was the most potent known phenethylamine psychedelic.<ref name="Shulgin1981" />

The drug acts as an agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A receptor.<ref name="Ray2010" /><ref name="RudinLuethiHoener2022" />

DOB was first synthesized by Alexander Shulgin in 1967 and was described by him and his colleagues in the scientific literature in 1971.<ref name="PiHKAL">Erowid Online Books: "PiHKAL" - #62 DOB</ref><ref name="ShulginSargentNaranjo1971">Template:Cite journal</ref> Shulgin subsequently further described the effects of DOB in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).<ref name="PiHKAL" />

Use and effects

In his book PiHKAL, Alexander Shulgin gives the dose range of DOB as 1 to 3Template:Nbspmg and its duration as 18 to 30Template:Nbsphours.<ref name="PiHKAL" /> In other publications, he specifies the dose range as 2 to 3Template:Nbspmg for racemic DOB and 1 to 2Template:Nbspmg for the preferentially active (R)-DOB enantiomer, while the duration is stated as being extremely long, a plateau occurring between 4 to 10Template:Nbsphours, and returning to baseline after 24 to 36Template:Nbsphours.<ref name="Shulgin1981" /> DOB was described as producing effects such as closed-eye and open-eye psychedelic visuals and introspection, among others.<ref name="PiHKAL" /><ref name="Shulgin1981" />

At a low sub-hallucinogenic dose of 0.4Template:Nbspmg DOB, the drug was also psychoactive and produced effects including enhanced visual perception, some strengthening of colors, enriched emotional affect, a comfortable and good feeling, and colorful and important dreams.<ref name="Shulgin1981" />

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.<ref name="Shulgin1981" />

Overdose

Overdose of DOB has been reported to produce cardiovascular symptoms and convulsions.<ref name="Shulgin1981" /> Excessively high doses of DOB may cause diffuse arterial spasm.<ref name="BowenDavisKearney1983">Template:Cite journal</ref> The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline.<ref name="BowenDavisKearney1983" /> A 35Template:Nbspmg overdose resulted in death, while a 75Template:Nbspmg overdose in a person with tolerance resulted in ergotism-like complications that required amputation.<ref name="Shulgin1981" />

Interactions

DOB may interact synergistically with alcohol.<ref name="Shulgin1981" />

Pharmacology

Pharmacodynamics

Template:Nowrap

Target	Affinity (Ki, nM)
5-HT1A	2,550–7,904
5-HT1B	941
5-HT1D	636
5-HT1E	556–1,427
5-HT1F	Template:Abbr
5-HT2A	0.6–81 (Ki) 0.52–50 (Template:Abbrlink) 57–105% (Template:Abbrlink)
5-HT2B	2.9–44 (Ki) 2.82–65 (Template:Abbr) 70–100% (Template:Abbr)
5-HT2C	1.3–78 (Ki) 0.25–102 (Template:Abbr) 58–112% (Template:Abbr)
5-HT3	>10,000
5-HT4	Template:Abbr
5-HT5A	5,311
5-HT6	5,535
5-HT7	506
α1A, α1B	>10,000
α1D	Template:Abbr
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
Template:Abbrlink	8,538 (Ki)
Template:Abbrlink	>10,000 (Ki)
Template:Abbrlink	>10,000 (Ki)
Template:Abbrlink	100,000 (Template:Abbrlink) (rat)
Template:Abbrlink	>100,000 (Template:Abbr) (rat)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="PDSPKiDatabase">Template:Cite web</ref><ref name="BindingDB">Template:Cite web</ref><ref name="Ray2010">Template:Cite journal</ref><ref name="vanWijngaardenSoudijn1997">Template:Cite book</ref><ref name="Acuña-CastilloVillalobosMoya2002">Template:Cite journal</ref><ref name="HemanthNistalaNguyen2023">Template:Cite journal</ref><ref name="Reyes-ParadaIturriaga-VasquezCassels2019">Template:Cite journal</ref><ref name="ScorzaCarrauSilveira1997">Template:Cite journal</ref><ref name="RudinLuethiHoener2022">Template:Cite journal</ref><ref name="WallachCaoCalkins2023">Template:Cite journal</ref><ref name="LewinMillerGilmour2011" />

DOB is a serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor agonist.<ref name="Ray2010" /><ref name="RudinLuethiHoener2022" /> 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.<ref name="LewinMillerGilmour2011">Template:Cite journal</ref><ref name="RudinLuethiHoener2022" /> In contrast to the serotonin releasing agent MDMA, DOB does not produce protein kinase C (PKC) activation in the brains of rodents in vivo.<ref name="KramerPobleteAzmitia1997">Template:Cite journal</ref><ref name="Kenneth1996">Template:Cite web</ref> The PKC activation by MDMA appears to be dependent on uptake by the serotonin transporter (SERT).<ref name="KramerPobleteAzmitia1997" /><ref name="Kenneth1996" />

DOB has been found to reduce aggression in rats.<ref name="MorrisonMelloni2014">Template:Cite book</ref><ref name="MuehlenkampLucionVogel1995">Template:Cite journal</ref>

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.<ref>Template:Cite journal</ref>

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.

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.Template:Citation needed Other analogues of DOB include 4C-B, Bromo-DragonFLY, DOB-FLY, and 25B-NBOMe, among others.

History

DOB was first synthesized by Alexander Shulgin in 1967.<ref name="PiHKAL" /> It was first described in the scientific literature in a paper by Shulgin, Claudio Naranjo, and another colleague in 1971.<ref name="ShulginSargentNaranjo1971" /> The Template:Abbrlink of DOB, brolamfetamine, was proposed and recommended by the World Health Organization (WHO) in 1986.<ref name="WHO1986a">Template:Cite web</ref><ref name="WHO1986b">Template:Cite web</ref> This was the same year that the Multidisciplinary Association for Psychedelic Studies (MAPS) was founded.<ref name="EmersonPontéJerome2014">Template:Cite journal</ref> DOB was registered with the WHO as a supposed "anorexic" (appetite suppressant).<ref name="WHO2024">Template:Cite web</ref>

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.<ref>Template:Cite web</ref>

Canada

Listed as a Schedule 1 as it is an analogue of amphetamine.<ref name="CDSA Schedule I: Amphetamines">Template:Cite web</ref>

Australia

DOB is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).<ref name="Poisons Standard">Template:Cite web</ref> 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.<ref name="Poisons Standard" />

Russia

Schedule I, possession of at least 10 mg is a criminal offence.<ref>Template:Cite web</ref>

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.<ref name="ShulginManningDaley2011">Template:Cite book</ref> It was scheduled in 1973.<ref name="Bartels1973">Template:Cite magazine</ref>

See also

• DOx

External links

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