2,5-Dimethoxy-4-bromoamphetamine

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DOB
Chemical name	(4-bromo-2,5-Dimethoxy-amphetamine or 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane
Chemical formula	C₁₁H₁₆BrNO₂
Molecular mass	274.15 g/mol
Melting point	63 - 65 °C 207 - 208 °C (hydrochloride)
CAS numbers	32156-26-6, 43061-15-0, 43061-16-1, 64638-07-9
SMILES	N[C@H](C)CC1=C(OC)C=C(Br)C(OC)=C1 (R-isomer)

DOB (or Bromo-DMA) is a psychedelic hallucinogenic drug 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 3 mg. 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.

1 Chemistry
2 Misrepresentation as LSD
3 Legality
4 External links
5 Categorization

[edit] Chemistry

The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. DOB has a stereocenter and R-(-)-DOB is the more active stereoisomer. The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction of the extremities.

Tabs of DOB, confiscated by police in Concord, California in 2006.

[edit] Misrepresentation as LSD

Although rare on the black market, sales of DOB on blotter paper, misrepresented as LSD or mescaline, and in tablet form, misrepresented as MDMA, have been reported. The misrepresentation as LSD has been described by the periodical "High Times" - this helped some users to find out what they were really taking. At least during mid- to late 1980s DOB was quite frequently sold as LSD either on blotter paper or as gelatine pyramids. ^{[citation needed]}

[edit] Legality

Internationally, DOB is a Schedule I drug under the Convention on Psychotropic Substances [1].

[edit] External links

[edit] Categorization

Hallucinogenic phenethylamines edit
2C-B, 2C-B-FLY, 2C-C, 2C-D, 2C-E, 2C-G, 2C-I, 2C-N, 2C-O, 2C-O-4, 2C-P, 2C-T, 2C-T-2, 2C-T-4, 2C-T-7, 2C-T-8, 2C-T-9, 2C-T-21, 2C-TFM, 3C-E, 3C-P, Br-DFLY, DESOXY, DMMDA-2, DOB, DOC, DOET, DOI, DOM, DON, Escaline, Isoproscaline, Lophophine, MDA, MMDA, Macromerine, Mescaline, Proscaline, TMA