2,5-Dimethoxy-4-bromoamphetamine

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2,5-Dimethoxy-4-bromoamphetamine
Chemical structure of (±)-DOB
DOB-3d-sticks.png
(R)-isomer
Identifiers
CAS number 64638-07-9 (racemate) N, 43061-15-0 (R), 43061-16-1 (S)
PubChem 62065
ChemSpider 55902 YesY
DrugBank DB01484
ChEMBL CHEMBL6607 YesY
IUPHAR ligand 155
Jmol-3D images Image 1
Properties
Molecular formula C11H16BrNO2
Molar mass 274.15 g/mol
Melting point 63-65 °C
207-208 °C (hydrochloride)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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][2] Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.

Chemistry[edit]

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 DOI, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors,[3] 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[edit]

DOB is a 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist.[4] 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 is an agonist of human TAAR1.[5]

It has been suggested that DOB is a prodrug metabolized in the lungs.[1][6]

Dosage[edit]

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[edit]

DOB has been sold on blotter paper (and presumably represented as LSD).[7][8] 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.[9] 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.[10][dubious ][unreliable source?]

Legal status[edit]

International[edit]

DOB is a Schedule I drug under the Convention on Psychotropic Substances.[11]

Canada[edit]

Listed as a Schedule 1 as it is an analogue of amphetamine.[12]

See also[edit]

References[edit]

  1. ^ a b c Erowid Online Books : "PiHKAL" - #62 DOB
  2. ^ 4-Bromo-2,5-Dimethoxyphenylisopropylamine, a New Centrally Active Amphetamine Analog. doi:10.1159/000136181. 
  3. ^ 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.
  4. ^ Ray, T. S. (2010). "Psychedelics and the Human Receptorome". PLoS ONE 5 (2): e9019. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400.  edit
  5. ^ "Articleid 50034244". Binding Database. Retrieved 29 April 2014. 
  6. ^ Shulgin (2005-05-03). "Ask Dr. Shulgin Online: DOB and Other Possible Prodrugs". Retrieved 18 November 2009. 
  7. ^ 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.
  8. ^ 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.
  9. ^ Delliou D (1980). "Bromo-DMA: new hallucinogenic drug". Med J Aust 1 (2): 83. PMID 7360100. 
  10. ^ http://www.erowid.org/chemicals/dob/dob_effects.shtml
  11. ^ "List of psychotropic substances under international control". Archived from the original on 2 March 2007. Retrieved 30 March 2007. 
  12. ^ [1] (English)

External links[edit]