View source for 2,5-Dimethoxy-4-bromoamphetamine

{{Refimprove|date=December 2007}}
{{chembox
| ImageFile1 = R-DOB.svg
| ImageSize1 = 200px
| ImageName1 = Chemical structure of (''R'')-DOB
| ImageFile2 = DOB-3d-sticks.png
| ImageSize2 = 200px
| IUPACName = 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane
| OtherNames = 4-Bromo-2,5-dimethoxy-amphetamine
| Section1 = {{Chembox Identifiers
| ChemSpiderID = 55902
| InChI = 1/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3
| InChIKey = FXMWUTGUCAKGQL-UHFFFAOYAD
| CASNo = 64638-07-9
| CASOther = (R): 43061-15-0<br>(S): 43061-16-1
| PubChem = 62065
| IUPHAR_ligand = 163
| IUPHAR_ligand = 155
| SMILES = Brc1cc(OC)c(cc1OC)CC(N)C
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>11</sub>H<sub>16</sub>BrNO<sub>2</sub>
| MolarMass = 274.15 g/mol
| Appearance = 
| Density = 
| MeltingPt = 63-65 °C<br>207-208 °C ([[hydrochloride]])
| BoilingPt = 
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards = 
| FlashPt = 
| Autoignition = }}
}}

'''DOB''', also known as '''Brolamfetamine''' and '''Bromo-DMA''', is a [[psychedelic]] [[Psychedelics, dissociatives and deliriants|hallucinogenic drug]] and a [[substituted amphetamine]] of the [[phenethylamine]] class of compounds, which can be used as an [[entheogen]].  DOB was first synthesized by [[Alexander Shulgin]] in 1967. In his book ''[[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]]'', Shulgin lists the dosage range as 1 to 3mg for the racemate. The enantiopure compound dosage is at least half of that. DOB is generally taken orally.  According to Shulgin, the effects of DOB typically last 18 to 30 hours.  Onset of the drug is also long, sometimes taking up to three hours. The substance has been described as a more lucid, more [[amphetamine]]-like version of [[LSD]], albeit far longer lasting. 

==Chemistry==
[[Image:DOB_blotters.jpg|thumb|left|100px|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]].  The toxicity of DOB is not fully known, although high doses may cause serious [[vasoconstriction]] of the extremities.  DOB is one of the most potent compounds in PiHKAL; while the active dose is similar to that of [[2,5-dimethoxy-4-iodoamphetamine|DOI]], another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors,<ref name="parrish-2005">Parrish JC, Braden MR, Gundy E & Nichols DE (2005). Differential phospholipase-C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem. 95: 1575-1584.</ref> making it likely to be slightly more dangerous than DOI in overdose, due to greater vasoconstrictive action.  Omission of the amphetamine related α-methyl leads to [[2C-B]], a vastly safer compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist.  

(DOB racemate) DOSAGE: 1.0 - 3.0 mg. DURATION: 18 - 30 h.<br />
(DOI racemate) DOSAGE: 1.5 - 4.0 mg. DURATION: 18 - 30 h.

(2C-B) DOSAGE: 12 - 25 mg. DURATION: 4 - 8 h.<br /> 
(2C-I) DOSAGE: 14 - 25 mg. DURATION: 6 - 8 h.

There was a report of a death of a young lady following the snorting of an amount of DOB so massive, over nine milligrams of the drug was recovered from her body tissues in the postmortem examination. It was said that she and her companion had thought that the drug they were using was MDMA and, taking a dosage appropriate for this, effectively overdosed themselves. He survived, following convulsions and an extended period (several weeks) of being in a comatose state. Tragic examples have been reported that involve arterial vascular spasm. But in most overdose cases ascribed to DOB, the identity of the drug has remained unestablished.<ref name="dob-pihkal">[http://www.erowid.org/library/books_online/pihkal/pihkal062.shtml Erowid Online Books : "PiHKAL" - #62 DOB<!-- Bot generated title -->]</ref>

==Pharmacology==

DOB is a selective [[5-HT2A receptor|5-HT<sub>2A</sub>]], [[5-HT2B receptor|5-HT<sub>2B</sub>]], and [[5-HT2C receptor|5-HT<sub>2C</sub> receptor]] [[partial agonist]]. Its psychedelic effects are mediated by its [[agonist]]ic properties at the 5-HT<sub>2A</sub> receptor. Due to its selectivity, DOB is often used in scientific research when studying the [[5-HT2|5-HT<sub>2</sub> receptor]] subfamily.

It has been suggested that DOB is a [[prodrug]] metabolized in the lungs.<ref name="dob-pihkal" /><ref>{{cite web|url=http://www.cognitiveliberty.org/shulgin/blg/2005/05/dob-and-other-possible-prodrugs.html |title=Ask Dr. Shulgin Online: DOB and Other Possible Prodrugs |accessdate=2009-11-18 |last=Shulgin |date=2005-05-03 }}</ref>

==Misrepresentation as LSD==
Sales of DOB on blotter paper, misrepresented as [[LSD]], and in tablet form, misrepresented as [[MDMA]] or [[mescaline]], have been frequently reported.{{Fact|date=September 2009}}  Misrepresentation as LSD could be potentially dangerous, as DOB does not have the known safety profile of LSD: unlike LSD, DOB can have physically harmful (if not fatal) effects in overdose.  The misrepresentation as LSD has been described by the periodical "[[High Times]]," helping some users to identify what they are actually taking.{{Fact|date=September 2009}}  Since the mid 1980s, DOB has appeared on blotter paper and has been accidentally (or purposefully) sold as LSD.{{Fact|date=September 2009}}  A common saying is,"If it's bitter, it's a spitter." Upon tasting the chemical, if one notices a highly bitter or "chemically" taste, this should serve as a warning sign that the drug is not LSD, but likely a psychedelic amphetamine (DOC, DOB or DOI). Although it must be noted that the absence of a ''bitter'' taste does not necessarily mean the blotter contains [[LSD]], detecting other blotter substrate drugs like [[5-MeO-AMT]] or [[Bromo-DragonFLY]], by taste, has not yet been reported.  An active dose of LSD (~100 μg) is so small that it has virtually no perceivable taste{{Fact|date=February 2010}}. On the contrary, according to the famous chemist Alexander Shulgin, the taste of LSD is "slightly bitter" (PIHKAL, p. 26).

==Legality==
Internationally, DOB is a Schedule I drug under the [[Convention on Psychotropic Substances]].<ref>{{cite web |url=http://www.incb.org/pdf/e/list/green.pdf |title= List of psychotropic substances under international control |accessdate= 2007-03-30}}</ref>

== See also ==
* [[2,5-Dimethoxy-4-Substituted Amphetamine]]s

== References ==
{{Reflist|2}}

== External links ==
* [http://www.erowid.org/library/books_online/pihkal/pihkal062.shtml DOB Entry in PiHKAL]
* [http://pihkal.info/read.php?domain=pk&id=62 DOB Entry in PiHKAL • info]
* [http://www.erowid.org/chemicals/dob/dob.shtml Erowid DOB Vault]

{{Hallucinogens}}
{{Serotonergics}}
{{Phenethylamines}}

{{DEFAULTSORT:Dimethoxy-4-bromoamphetamine, 2,5-}}
[[Category:Serotonin receptor agonists]]
[[Category:Amphetamines]]
[[Category:Organobromides]]
[[Category:Phenol ethers]]

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[[Category:2Fix]]