2,5-Dimethoxy-4-bromoamphetamine

{{Short description|Chemical compound}} {{use dmy dates|cs1-dates=ly|date=November 2024}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 477192160 | drug_name = DOB | INN = Brolamfetamine | image = DOB-racemic-skeletal.svg | image_class = skin-invert-image | width = 200px | caption = Chemical structure of (±)-DOB | image2 = DOB-3d-sticks.png | image_class2 = bg-transparent | width2 = 175px | caption2 = Ball-and-stick model of (''R'')-DOB

<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /><ref name="Shulgin1981" /> | class = Serotonin 5-HT₂ receptor agonist; Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =

<!-- Legal status --> | legal_AU = Schedule 9 | legal_BR = F2 | legal_BR_comment = <ref>{{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}</ref> | legal_CA = Schedule I | legal_DE = <!-- Anlage I, II, III or Unscheduled --> | legal_NZ = <!-- Class A, B, C --> | legal_UK = Class A | legal_US = Schedule I | legal_EU = | legal_UN = P I | legal_status =

<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = 1–2 hours<ref name="PiHKAL" /><ref name="Shulgin1981" /><br />Peak: 3–4 hours<ref name="PiHKAL" /><ref name="Shulgin1981" /> | elimination_half-life = | duration_of_action = 18–36 hours<ref name="PiHKAL" /><ref name="Shulgin1981" /> | excretion =

<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 64638-07-9 | CAS_supplemental = {{nbsp}}(racemate)<br />[https://commonchemistry.cas.org/detail?cas_rn=43061-15-0 43061-15-0] (''R''-isomer)<br />[https://commonchemistry.cas.org/detail?cas_rn=43061-16-1 43061-16-1] (''S''-isomer) | PubChem = 62065 | PubChemSubstance = 46507989 | IUPHAR_ligand = 155 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01484 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 55902 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 67WJC4Y2QY | KEGG = D12707 | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 6607 | NIAID_ChemDB = | PDB_ligand = | synonyms = DOB; 4-Bromo-2,5-dimethoxyamphetamine; Brolamfetamine; Brolamphetamine; Bromo-DMA; 2,5-Dimethoxy-4-bromo-α-methylphenethylamine; 4-Bromo-2,5-dimethoxyphenyl-isopropylamine

<!-- Chemical data --> | IUPAC_name = 1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine | C=11 | H=16 | Br=1 | N=1 | O=2 | SMILES = CC(CC1=CC(=C(C=C1OC)Br)OC)N | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FXMWUTGUCAKGQL-UHFFFAOYSA-N

<!-- Physical data --> | melting_point = 63-65 | melting_notes = <br />(207–208&nbsp;°C hydrochloride) }}

'''2,5-Dimethoxy-4-bromoamphetamine''' ('''DOB'''), also known as '''brolamfetamine''' ({{Abbrlink|INN|International Nonproprietary Name}}),<ref name="Organization2000">{{cite book|author=World Health Organization|title=International Nonproprietary Names (INN) for Pharmaceutical Substances|url=https://books.google.com/books?id=HcogPwAACAAJ|year=2000|publisher=World Health Organization|isbn=978-0-11-986227-0}}</ref> is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.<ref name="PiHKAL" /><ref name="Shulgin1981">{{cite journal | vauthors = Shulgin A | title = Profiles of Psychedelic Drugs: 10. DOB | journal = J Psychoactive Drugs | volume = 13 | issue = 1 | pages = 99 | date = 1981 | pmid = 7277091 | doi = 10.1080/02791072.1981.10471457 | url = https://bibliography.maps.org/resources/download/8845 | archive-url = https://web.archive.org/web/20250712232007/https://bibliography.maps.org/resources/download/8845 | archive-date = 12 July 2025 }}</ref> For many years, prior to the discovery of newer compounds, DOB was the most potent known phenethylamine psychedelic.<ref name="PiHKAL" /><ref name="Shulgin1981" /> It is taken orally.<ref name="PiHKAL" /><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" /> Analogues of DOB include 2C-B, DOM, DOI, and Bromo-DragonFLY (DOB-DFLY), among others.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" />

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">[http://www.erowid.org/library/books_online/pihkal/pihkal062.shtml Erowid Online Books: "PiHKAL" - #62 DOB]</ref><ref name="ShulginSargentNaranjo1971">{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = 4-Bromo-2,5-dimethoxyphenylisopropylamine, a new centrally active amphetamine analog | journal = Pharmacology | volume = 5 | issue = 2 | pages = 103–107 | year = 1971 | pmid = 5570923 | doi = 10.1159/000136181 | s2cid = 46844380 | url = http://repositorio.uchile.cl/handle/2250/162196 }}</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'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists DOB's dose as 1 to 3{{nbsp}}mg orally and its duration as 18 to 30{{nbsp}}hours.<ref name="PiHKAL" /> In an earlier publication, he listed its dose as 2 to 3{{nbsp}}mg for racemic DOB and 1 to 2{{nbsp}}mg for the preferentially active (''R'')-DOB enantiomer.<ref name="PiHKAL" /> In addition, he described the duration as being extremely long, with a gradual descent and baseline being achieved after 24 to 36{{nbsp}}hours.<ref name="Shulgin1981" /><ref name="PiHKAL" /> The onset has been described as 1 to 2{{nbsp}}hours, the time to peak as 3 or 4{{nbsp}}hours, and a plateau occurring from 4 to 10{{nbsp}}hours.<ref name="PiHKAL" /><ref name="Shulgin1981" /> Its onset is said to be relatively slow.<ref name="PiHKAL" />

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.<ref name="PiHKAL" /><ref name="Shulgin1981" /> At a low dose of 0.4{{nbsp}}mg DOB, there was only enhanced visual perception, strengthening of colors, enriched emotional affect, a comfortable good feeling, and colorful and important dreams.<ref name="PiHKAL" />

(''R'')-DOB produced moderate effects at a dose of 0.5{{nbsp}}mg and pronounced effects at 1.0 to 1.5{{nbsp}}mg, whereas there were no effects with 0.5{{nbsp}}mg (''S'')-DOB and only threshold and very slight effects with 1.0{{nbsp}}mg (''S'')-DOB.<ref name="PiHKAL" /> In relation to this, (''R'')-DOB is described as the more active enantiomer and (''S'')-DOB as much less active.<ref name="PiHKAL" /> In one report, 1{{nbsp}}mg (''R'')-DOB was described as not as strong as 2{{nbsp}}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.<ref name="PiHKAL" /> (''S'')-DOB has never been tested up to fully active doses.<ref name="PiHKAL" /> In another source however, by Richard Glennon and colleagues, the approximate hallucinogenic dose was listed as 0.8 to 2.0{{nbsp}}mg for racemic DOB, 0.5{{nbsp}}mg for (''R'')-DOB, and 5.0{{nbsp}}mg for (''S'')-DOB.<ref name="GlennonRosecrans1982">{{cite journal | vauthors = Glennon RA, Rosecrans JA | title = Indolealkylamine and phenalkylamine hallucinogens: a brief overview | journal = Neurosci Biobehav Rev | volume = 6 | issue = 4 | pages = 489–497 | date = 1982 | pmid = 6757811 | doi = 10.1016/0149-7634(82)90030-6 | url = }}</ref>

==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="PiHKAL" /><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">{{cite journal | vauthors = Bowen JS, Davis GB, Kearney TE, Bardin J | title = Diffuse vascular spasm associated with 4-bromo-2,5-dimethoxyamphetamine ingestion | journal = JAMA | volume = 249 | issue = 11 | pages = 1477–1479 | date = March 1983 | pmid = 6827726 | doi = 10.1001/jama.1983.03330350053028 }}</ref> The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline.<ref name="BowenDavisKearney1983" /> A 35{{nbsp}}mg overdose resulted in death, while a 75{{nbsp}}mg overdose in a person with tolerance resulted in ergotism-like complications that required amputation.<ref name="Shulgin1981" />

==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

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

==Pharmacology== ===Pharmacodynamics=== {| class="wikitable floatleft" style="font-size:small;" |+ {{Nowrap|DOB activities}} |- ! Target !! Affinity (K_i, nM) |- | 5-HT_1A || 2,550–7,904 |- | 5-HT_1B || 941 |- | 5-HT_1D || 636 |- | 5-HT_1E || 556–1,427 |- | 5-HT_1F || {{Abbr|ND|No data}} |- | 5-HT_2A || 0.6–81 (K_i)<br />0.52–50 ({{Abbrlink|EC₅₀|half-maximal effective concentration}})<br />57–105% ({{Abbrlink|E_max|maximal efficacy}}) |- | 5-HT_2B || 2.9–44 (K_i)<br />2.82–65 ({{Abbr|EC₅₀|half-maximal effective concentration}})<br />70–100% ({{Abbr|E_max|maximal efficacy}}) |- | 5-HT_2C || 1.3–78 (K_i)<br />0.25–102 ({{Abbr|EC₅₀|half-maximal effective concentration}})<br />58–112% ({{Abbr|E_max|maximal efficacy}}) |- | 5-HT₃ || >10,000 |- | 5-HT₄ || {{Abbr|ND|No data}} |- | 5-HT_5A || 5,311 |- | 5-HT₆ || 5,535 |- | 5-HT₇ || 506 |- | α_1A, α_1B || >10,000 |- | α_1D || {{Abbr|ND|No data}} |- | α_2A || 4,266 |- | α_2B || 1,527 |- | α_2C || 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 |- | {{Abbrlink|SERT|Serotonin transporter}} || 8,538 (K_i) |- | {{Abbrlink|NET|Norepinephrine transporter}} || >10,000 (K_i) |- | {{Abbrlink|DAT|Dopamine transporter}} || >10,000 (K_i) |- | {{Abbrlink|MAO-A|Monoamine oxidase A}} || 100,000 ({{Abbrlink|IC₅₀|half-maximal inhibitory concentration}}) (rat) |- | {{Abbrlink|MAO-B|Monoamine oxidase B}} || >100,000 ({{Abbr|IC₅₀|half-maximal inhibitory concentration}}) (rat) |- class="sortbottom" | colspan="2" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''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">{{cite web | title=PDSP Database | website=UNC | url=https://pdsp.unc.edu/databases/pdsp.php?receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=dob&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query | language=zu | access-date=4 February 2025}}</ref><ref name="BindingDB">{{cite web | vauthors = Liu T | title=BindingDB BDBM50005257 (+)-2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(+)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(+/-)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(-)-2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(-)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine::2-(2-Methoxy-phenyl)-1-methyl-ethylamine::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((-)-DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((R)-(-)-DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((S)-(+)-DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine(DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine[R(-)DOB]::2-(5-Bromo-2,4-dimethoxy-phenyl)-1-methyl-ethylamine::Brolamfetamine::CHEMBL6607::DOB::Racemic DOB | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50005257 | access-date=4 February 2025}}</ref><ref name="Ray2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 |article-number=e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R }}</ref><ref name="vanWijngaardenSoudijn1997">{{cite book | vauthors = van Wijngaarden I, Soudijn W | title=Pharmacochemistry Library | chapter=5-HT2A, 5-HT2B and 5-HT2C receptor ligands | publisher=Elsevier | volume=27 | date=1997 | isbn=978-0-444-82041-9 | doi=10.1016/s0165-7208(97)80013-x | pages=161–197}}</ref><ref name="Acuña-CastilloVillalobosMoya2002">{{cite journal | vauthors = Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP | title = Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors | journal = Br J Pharmacol | volume = 136 | issue = 4 | pages = 510–519 | date = June 2002 | pmid = 12055129 | pmc = 1573376 | doi = 10.1038/sj.bjp.0704747 | url = }}</ref><ref name="HemanthNistalaNguyen2023">{{cite journal | vauthors = Hemanth P, Nistala P, Nguyen VT, Eltit JM, Glennon RA, Dukat M | title = Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT_2A and 5-HT_2B serotonin receptors | journal = Frontiers in Pharmacology | volume = 14 | issue = | article-number = 1101290 | date = 2023 | pmid = 36762110 | pmc = 9902381 | doi = 10.3389/fphar.2023.1101290 | doi-access = free }}</ref><ref name="Reyes-ParadaIturriaga-VasquezCassels2019">{{cite journal | vauthors = Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK | title = Amphetamine Derivatives as Monoamine Oxidase Inhibitors | journal = Front Pharmacol | volume = 10 | issue = | article-number = 1590 | date = 2019 | pmid = 32038257 | pmc = 6989591 | doi = 10.3389/fphar.2019.01590 | doi-access = free | url = }}</ref><ref name="ScorzaCarrauSilveira1997">{{cite journal | vauthors = Scorza MC, Carrau C, Silveira R, Zapata-Torres G, Cassels BK, Reyes-Parada M | title = Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships | journal = Biochem Pharmacol | volume = 54 | issue = 12 | pages = 1361–1369 | date = December 1997 | pmid = 9393679 | doi = 10.1016/s0006-2952(97)00405-x | url = https://repositorio.uchile.cl/handle/2250/157599}}</ref><ref name="RudinLuethiHoener2022">{{cite journal | vauthors = Rudin D, Luethi D, Hoener MC, Liechti ME | title=Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues | journal=The FASEB Journal | volume=36 | issue=S1 | date=2022 | article-number=fasebj.2022.36.S1.R2121 | issn=0892-6638 | doi=10.1096/fasebj.2022.36.S1.R2121 | doi-access=free | url=https://www.researchgate.net/publication/360423277}}</ref><ref name="WallachCaoCalkins2023">{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | article-number = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | bibcode = 2023NatCo..14.8221W }}</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">{{cite journal | vauthors = Lewin AH, Miller GM, Gilmour B | title = Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class | journal = Bioorganic & Medicinal Chemistry | volume = 19 | issue = 23 | pages = 7044–7048 | date = December 2011 | pmid = 22037049 | pmc = 3236098 | doi = 10.1016/j.bmc.2011.10.007 }}</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">{{cite journal | vauthors = Kramer HK, Poblete JC, Azmitia EC | title = Activation of protein kinase C (PKC) by 3,4-methylenedioxymethamphetamine (MDMA) occurs through the stimulation of serotonin receptors and transporter | journal = Neuropsychopharmacology | volume = 17 | issue = 3 | pages = 117–129 | date = September 1997 | pmid = 9272479 | doi = 10.1016/S0893-133X(97)00026-2 | url = }}</ref><ref name="Kenneth1996">{{cite web | vauthors = Kenneth H | title=Evidence for the involvement of the serotonin uptake transporter and the serotonin-2 receptor in the activation of protein kinase C (PKC) by substituted amphetamines in the adult rodent brain | date=1996 | website=ProQuest | publisher=New York University | url=https://www.proquest.com/openview/7fd77d32ea08d8335780ab0d4409b427/1?pq-origsite=gscholar&cbl=18750&diss=y | access-date=1 February 2025 | quote=MDMA manifests its acute psychotropic and neurotoxic effects by releasing 5-HT from nerve endings. MDMA also shows a moderate agonist-like affinity (1.5-3.2 mM [(sic)]) for the central 5-HT2 receptor. Activation of this receptor stimulates the translocation/activation of protein kinase C (PKC) and the release of Ca2+ from intracellular sequestration sites. MDMA has already been shown to increase [Ca2+], and this may proceed through the activation of this receptor. [...] In vivo, both MDMA and PCA were found to produce a lasting translocation of [protein kinase C (PKC)] in the cortex and hippocampus of treated rats. Fluoxetine, a 5-HT uptake inhibitor, prevents PKC translocation, while ketanserin, a 5-HT2A antagonist, acts similarly but a diminished efficacy. Non-neurotoxic drugs like fluoxetine, DOB, and cocaine were devoid of MDMA's long-term PKC translocating abilities, and suggests that receptor stimulation alone is not the sole mechanism. In synaptosomes, MDMA was effective at producing PKC translocation by binding to the 5-HT uptake carner. This in vitro response [of] fluoxetine reverses this response and demonstrates that MDMA translocates PKC within the 5-HT nerve terminal.}}</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">{{cite book | vauthors = Morrison TR, Melloni RH | title = Neuroscience of Aggression | chapter = The role of serotonin, vasopressin, and serotonin/vasopressin interactions in aggressive behavior | series = Curr Top Behav Neurosci | volume = 17 | pages = 189–228 | date = 2014 | pmid = 24496652 | doi = 10.1007/7854_2014_283 | isbn = 978-3-662-44280-7 | chapter-url = | quote = Another 5HT2A receptor partial agonist, DOB, has a marginally higher affinity for the 5HT2A receptor (in its low affinity state) than DOI (Roth et al. 1997), and in the water competition (WC) test it has been shown to block defensive aggression in rats. Interestingly, DOI also reduced the number of offensive aggressive behaviors (i.e., attacks, greater latency to first attack, shorter attack duration) in the same animals that exhibited DOI-induced reductions in defensive behaviors during the WC test (Muehlenkamp et al. 1995).}}</ref><ref name="MuehlenkampLucionVogel1995">{{cite journal | vauthors = Muehlenkamp F, Lucion A, Vogel WH | title = Effects of selective serotonergic agonists on aggressive behavior in rats | journal = Pharmacology Biochemistry and Behavior | volume = 50 | issue = 4 | pages = 671–674 | date = April 1995 | pmid = 7617717 | doi = 10.1016/0091-3057(95)00351-7 | s2cid = 12774131 }}</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>{{cite journal | vauthors = Parrish JC, Braden MR, Gundy E, Nichols DE | title = Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists | journal = Journal of Neurochemistry | volume = 95 | issue = 6 | pages = 1575–1584 | date = December 2005 | pmid = 16277614 | doi = 10.1111/j.1471-4159.2005.03477.x | s2cid = 24005602 | doi-access = free }}</ref>

==Chemistry== [[Image:DOB blotters.jpg|thumb|right|upright|Tabs of DOB, confiscated by police in Concord, California in 2006.]]

The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine.<ref name="PiHKAL" /> 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.<ref name="PiHKAL" />

===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.{{Citation needed|date=December 2017}} 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.<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 {{Abbrlink|INN|International Nonproprietary Name}} of DOB, ''brolamfetamine'', was proposed and recommended by the World Health Organization (WHO) in 1986.<ref name="WHO1986a">{{cite web | title=INN Proposed List 55 | website= World Health Organization (WHO) | date=9 April 1986 | url=https://www.who.int/publications/m/item/inn-pl-55 | ref={{sfnref| World Health Organization (WHO) |1900}} | access-date=3 November 2024}}</ref><ref name="WHO1986b">{{cite web | title=INN Recommended List 26 | website= World Health Organization (WHO) | date=9 June 1986 | url=https://www.who.int/publications/m/item/inn-rl-26 | ref={{sfnref| World Health Organization (WHO) |1900}} | access-date=3 November 2024}}</ref> This was the same year that the Multidisciplinary Association for Psychedelic Studies (MAPS) was founded.<ref name="EmersonPontéJerome2014">{{cite journal | vauthors = Emerson A, Ponté L, Jerome L, Doblin R | title = History and future of the Multidisciplinary Association for Psychedelic Studies (MAPS) | journal = J Psychoactive Drugs | volume = 46 | issue = 1 | pages = 27–36 | date = 2014 | pmid = 24830183 | doi = 10.1080/02791072.2014.877321 | url = https://www.researchgate.net/publication/262381557}}</ref> DOB was registered with the WHO as a supposed "anorexic" (appetite suppressant).<ref name="WHO2024">{{cite web | vauthors = ((World Health Organization)) | title=Use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances, 2024 | publisher = World Health Organization | date = 2024 | url=https://iris.who.int/bitstream/handle/10665/379226/9789240099388-eng.pdf#page=158 | access-date=21 October 2024 | pages=152–153}}</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>{{cite web|url=http://www.incb.org/pdf/e/list/green.pdf |title=List of psychotropic substances under international control |access-date=30 March 2007 |archive-url=https://web.archive.org/web/20070302130637/http://www.incb.org/pdf/e/list/green.pdf |archive-date=2 March 2007 |url-status=dead }}</ref>

====Canada==== Listed as a Schedule 1 as it is an analogue of amphetamine.<ref name="CDSA Schedule I: Amphetamines">{{cite web | title = (15) 4-Bromo-2,5-dimethoxyamphetamine (4-Bromo-2,5-dimethoxy-α-methylbenzeneethanamine) | url = http://isomerdesign.com/Cdsa/schedule.php?schedule=3&section=1&structure=C| archive-url = https://web.archive.org/web/20211123123506/http://isomerdesign.com/Cdsa/schedule.php?schedule=3&section=1&structure=C | archive-date=2021-11-23 | work = Isomer Design }}</ref>

====Australia==== DOB is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).<ref name="Poisons Standard">{{cite web | author = Department of Health and Aged Care | work = Federal Register of Legislation | publisher = Australian Government | title = Poisons Standard | date = October 2015 | url = https://www.comlaw.gov.au/Details/F2015L01534 }}</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&nbsp;mg is a criminal offence.<ref>{{cite web|url=http://base.garant.ru/70237124/ | work = Постановление Правительства РФ от 01.10.2012 N 1002 | title = Об утверждении значительного, крупного и особо крупного размеров наркотических средств и психотропных веществ, а также значительного, крупного и особо крупного размеров для растений, содержащих наркотические средства или психотропные вещества, либо их частей, содержащих наркотические средства или психотропные вещества, для целей статей 228, 228.1, 229 и 229.1 Уголовного кодекса Российской Федерации | trans-work = Resolution of the Government of the Russian Federation of 01.10.2012 N 1002 | trans-title = On approval of significant, large and especially large sizes of narcotic drugs and psychotropic substances, as well as significant, large and especially large sizes for plants containing narcotic drugs or psychotropic substances, or their parts containing narcotic drugs or psychotropic substances, for the purposes of Articles 228, 228.1, 229 and 229.1 of the Criminal Code of the Russian Federation | language = ru }}</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">{{cite book | vauthors = Shulgin A, Manning T, Daley PF | title=The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher=Transform Press | location=Berkeley | volume=1 | year=2011 | isbn=978-0-9630096-3-0 | page=102 }}</ref> It was scheduled in 1973.<ref name="Bartels1973">{{Cite magazine | vauthors = Bartels Jr JR |date=September 14, 1973 |title=Part 308 – Schedules of Controlled Substances; Additions to Schedule I |magazine=Federal Register |volume=38 |number=183 |article-number=26447–8 |publisher=Drug Enforcement Administration |url=https://isomerdesign.com/Cdsa/FR/38FR26447.pdf |access-date=September 30, 2023 |via=Isomer Design |archive-url=https://web.archive.org/web/20220303023114/https://isomerdesign.com/Cdsa/FR/38FR26447.pdf |archive-date=March 3, 2022}}</ref>

==See also== * DOx (psychedelics)

==References== {{Reflist}}

==External links== * [https://isomerdesign.com/pihkal/explore/62 DOB - Isomer Design] * [https://psychonautwiki.org/wiki/DOB DOB - PsychonautWiki] * [https://www.erowid.org/chemicals/dob/dob.shtml DOB - Erowid] * [https://tripsit.me/factsheets/dob DOB - TripSit] * [https://www.bluelight.org/xf/threads/325595 The Big & Dandy DOB Thread - Bluelight] * [http://www.erowid.org/library/books_online/pihkal/pihkal062.shtml DOB - PiHKAL - Erowid] * [http://pihkal.info/read.php?domain=pk&id=62 DOB - PiHKAL - Isomer Design]

{{Psychedelics}} {{Serotonin receptor modulators}} {{TAAR modulators}} {{Phenethylamines}}

{{DEFAULTSORT:Dimethoxy-4-bromoamphetamine, 2,5-}}

Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:Bromobenzene derivatives Category:Designer drugs Category:DOx (psychedelics) Category:PiHKAL Category:Serotonin receptor agonists Category:TAAR1 agonists