2,5-Dimethoxy-4-bromoamphetamine

2,5-Dimethoxy-4-bromoamphetamine
Chemical structure of (R)-DOB
File:DOB-3d-sticks.png
IUPAC name 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane
Other names 4-Bromo-2,5-dimethoxy-amphetamine
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	64638-07-9, (R): 43061-15-0 (S): 43061-16-1
PubChem	62065
ChemSpider	55902
IUPHAR ligand	155
SMILES
InChI
InChI key	FXMWUTGUCAKGQL-UHFFFAOYAD
style="background: #F8EABA; text-align: center;" colspan="2" | 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, 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. In his book 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

File:DOB blotters.jpg

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, 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.
(DOI racemate) DOSAGE: 1.5 - 4.0 mg. DURATION: 18 - 30 h.

(2C-B) DOSAGE: 12 - 25 mg. DURATION: 4 - 8 h.
(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.

Pharmacology

DOB is a selective 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.

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. 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. Since the mid 1980s, DOB has appeared on blotter paper and has been accidentally (or purposefully) sold as LSD. 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. 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.

See also

• 2,5-Dimethoxy-4-Substituted Amphetamines

External links

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

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