2,5-Dimethoxy-4-bromoamphetamine
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 (R)-isomer
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| IUPAC name
1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane
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| Other names
4-Bromo-2,5-dimethoxy-amphetamine
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| Identifiers | |
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3D model (JSmol)
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| ChEMBL | |
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| DrugBank | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C11H16BrNO2 | |
| Molar mass | 274.15 g/mol |
| Melting point | 63-65 °C 207-208 °C (hydrochloride) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dimethoxybromoamphetamine (DOB), also known as Brolamfetamine and Bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967.[1] Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.
Chemistry
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 DOI, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors,[2] 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 compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist which results in drastically reduced vasoconstriction.
Pharmacology
DOB is a 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist. Its psychedelic effects are mediated by its agonistic properties at the 5-HT2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT2 receptor subfamily.
It has been suggested that DOB is a prodrug metabolized in the lungs.[1][3]
Dosage
Shulgin lists the dosage range as 1 to 3 mg 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.
Shulgin states that 'the LD/50 was somewhere between 100 and 125 mg/kg for the mouse', but goes on to write that 'it is very likely that the damaging, if not lethal, level of DOB in man is a lot lower than this ratio would imply.'[1]
Misrepresentation as LSD
 | This section possibly contains original research. (October 2010) |
DOB has been sold on blotter paper (and presumably represented as LSD).[4][5] 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.[citation needed] Since the mid-1980s, DOB has appeared on blotter paper and has been accidentally (or purposefully) sold as LSD.[6] 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 (DOB, DOC, DOI or Bromo-DragonFLY).[citation needed] However, blotter paper may have a taste regardless of the chemical on it, due to ink or solvent used. Moreover, DOB like other drugs of its class like DOM, DOC, and DOI, have a different dose response curve than LSD, and they may take up to 3-6 hours to take full effect . Unsuspecting users who believe they are taking LSD may not notice the full effect of the DOB after the first to third hour or so and then redose because they think their dose was not very strong, thereby accidentally overdosing themselves. Additionally, unique to this compound, the amount of time it takes for the DOB effects to begin increases with the larger of a dose taken, especially when used in conjunction with alcohol.[7][dubious – discuss][unreliable source?]
Legal status
International
DOB is a Schedule I drug under the Convention on Psychotropic Substances.[8]
Canada
Listed as a Schedule 1 as it is an analogue of amphetamine.[9]
See also
- 2,5-Dimethoxy-4-Substituted Amphetamines
- 2C-B - the alpha-desmethyl derivative of DOB
References
- ^ a b c Erowid Online Books : "PiHKAL" - #62 DOB
- ^ 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.
- ^ Shulgin (2005-05-03). "Ask Dr. Shulgin Online: DOB and Other Possible Prodrugs". Retrieved 2009-11-18.
- ^ Drug Enforcement Administration. (2009) Blotter acid mimic (actually containing a mixture of 4-chloro-2,5,dimethoxyamphetamine and 4-bromo-2,5-dimethoxyamphetamine) in Warner Robins, Georgia. Microgram Bulletin. 42: 23 - 32.
- ^ Drug Enforcement Administration. (2009) Blotter acid mimic (actually containing 4-bromo-2,5-dimethoxy-amphetamine (DOB) and 4-chloro-2,5-dimethoxy-amphetamine (DOC)) in Pratt County, Kansas. Microgram Bulletin. 42: 33 - 44.
- ^ Delliou D (1980). "Bromo-DMA: new hallucinogenic drug". Med J Aust. 1 (2): 83. PMID 7360100.
- ^ http://www.erowid.org/chemicals/dob/dob_effects.shtml
- ^ "List of psychotropic substances under international control" (PDF). Archived from the original (PDF) on 2 March 2007. Retrieved 2007-03-30.
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