2,5-Dimethoxy-4-bromoamphetamine

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2,5-Dimethoxy-4-bromoamphetamine
Chemical structure of (±)-DOB
DOB-3d-sticks.png
(R)-isomer
Names
IUPAC name
1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane
Other names
4-Bromo-2,5-dimethoxy-amphetamine
Identifiers
64638-07-9 (racemate) N
43061-15-0 (R) N
43061-16-1 (S) N
ChEMBL ChEMBL6607 YesY
ChemSpider 55902 YesY
DrugBank DB01484 YesY
155
Jmol-3D images Image
PubChem 62065
Properties
C11H16BrNO2
Molar mass 274.15 g/mol
Melting point 63 to 65 °C (145 to 149 °F; 336 to 338 K)
(207–208 °C hydrochloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN)[1] 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.[2][3] 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,[4] 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.[5] 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.[6]

It has been suggested that DOB is a prodrug metabolized in the lungs.[2][7]

Legal status[edit]

International[edit]

DOB is a Schedule I drug under the Convention on Psychotropic Substances.[8]

Canada[edit]

Listed as a Schedule 1 as it is an analogue of amphetamine.[9]

See also[edit]

References[edit]

  1. ^ World Health Organization (2000). International Nonproprietary Names (INN) for Pharmaceutical Substances. World Health Organization. ISBN 978-0-11-986227-0. 
  2. ^ a b Erowid Online Books : "PiHKAL" - #62 DOB
  3. ^ "4-Bromo-2,5-Dimethoxyphenylisopropylamine, a New Centrally Active Amphetamine Analog". doi:10.1159/000136181. 
  4. ^ 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.
  5. ^ 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
  6. ^ "Articleid 50034244". Binding Database. Retrieved 29 April 2014. 
  7. ^ Shulgin (2005-05-03). "Ask Dr. Shulgin Online: DOB and Other Possible Prodrugs". Retrieved 18 November 2009. 
  8. ^ "List of psychotropic substances under international control" (PDF). Archived (PDF) from the original on 2 March 2007. Retrieved 30 March 2007. 
  9. ^ [1] (English)

External links[edit]