2,5-Dimethoxy-4-bromoamphetamine

2,5-Dimethoxy-4-bromoamphetamine
IUPAC name 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane
Other names 4-Bromo-2,5-dimethoxy-amphetamine
Identifiers
CAS number	64638-07-9, (R): 43061-15-0 (S): 43061-16-1
PubChem	62065
ChemSpider	55902 Y
DrugBank	DB01484
ChEMBL	CHEMBL6607 Y
IUPHAR ligand	155
Jmol-3D images	Image 1
SMILES Brc1cc(OC)c(cc1OC)CC(N)C
InChI InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 Y Key: FXMWUTGUCAKGQL-UHFFFAOYSA-N Y 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 Key: FXMWUTGUCAKGQL-UHFFFAOYAD
Properties
Molecular formula	C11H16BrNO2
Molar mass	274.15 g/mol
Melting point	63-65 °C 207-208 °C (hydrochloride)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic 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.^{[citation needed]} In his book PiHKAL (Phenethylamines i Have Known And Loved), 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. The substance has been described as a more lucid, more amphetamine-like version of LSD, albeit far longer lasting.

Chemistry

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,^[1] 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.^{[citation needed]}

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 MDA 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.^[2]

Pharmacology

DOB is a 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor partial agonist. 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 has been suggested that DOB is a prodrug metabolized in the lungs.^[2][3]

Misrepresentation as LSD

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.^{[citation needed]} 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.

Legality

Internationally, DOB is a Schedule I drug under the Convention on Psychotropic Substances.^[6]

See also

• 2,5-Dimethoxy-4-Substituted Amphetamines

References

1. ^ 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.
2. ^ ^{a b} Erowid Online Books : "PiHKAL" - #62 DOB
3. ^ Shulgin (2005-05-03). "Ask Dr. Shulgin Online: DOB and Other Possible Prodrugs". http://www.cognitiveliberty.org/shulgin/blg/2005/05/dob-and-other-possible-prodrugs.html. Retrieved 2009-11-18. 
4. ^ 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.
5. ^ 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.
6. ^ "List of psychotropic substances under international control". http://www.incb.org/pdf/e/list/green.pdf. Retrieved 2007-03-30. 

External links

• DOB Entry in PiHKAL
• DOB Entry in PiHKAL • info
• Erowid DOB Vault