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Chemical name 4-chloro-2,5-Dimethoxy-amphetamine or
Chemical formula C11H16NO2
Molar mass 229.70628 \begin{matrix} \frac{g}{mol} \end{matrix}
266.16692 \begin{matrix} \frac{g}{mol} \end{matrix} (hydrochloride salt)
Melting point 187-188 °C and 193-194.5 (hydrochloride)
CAS numbers  ?
SMILES COc1cc(C[C@@H](C)N)c(cc1Cl)OC

4-Chloro-2,5-dimethoxyamphetamine or 2,5-dimethoxy-4-chloroamphetamine or 4-Chloro-2,5-DMA or DOC is a psychedelic hallucinogenic drug of the phenethylamine family. Used by some as an entheogen, DOC was presumably first synthesized by Alexander Shulgin. The drug is generally taken orally, but some users have been known to insufflate or smoke the pure powder.


DOC is a substituted alpha-methylated phenethylamine, a class of compounds commonly known as amphetamines. The full name of the chemical is 2,5-dimethoxy-4-chloro-amphetamine. DOC has a stereocenter and R-(-)-DOC is the more active stereoisomer. DOC is the 3-carbon chain homologue of the psychedelic 2C-C.


A normal average dose of DOC ranges from .5-8.0 mg; the former producing threshold effects, and the latter producing extremely strong effects. Doses up to 10mg have been known to send the user into a restless stupor. Onset of the drug is 1-3 hours, peak and plateau at 4-8 hours, and a gradual come down. After effects can last well into the next day.


Unlike simple amphetamines, DOC is a psychedelic that resembles LSD, DOB, and amphetamines. These effects include open and closed eye visuals, increased appreciation of music, increased awareness of sound and movement and euphoria.


The mechanism of DOC’s hallucinogenic effects is unknown, but like DOB and DOI, it may be mediated by partial agonistic activity at the 5-HT2A serotonin receptor, and binding affinity for the 5-HT2B and the 5-HT2C serotonin receptor.


The toxicity of DOC is not known, but nausea, chest pains, and vasoconstriction have been reported by some users. In June 2006 four teenagers were admitted to a hospital in Metropolitan Detroit, Michigan after accidentally overdosing DOC.[1] To date, there have been no deaths attributed to DOC. However, DOC is an extremely potent psychoactive, and the risk of overdose is great if unknown or extreme dosages are taken.


Although rare on the black market, sales of DOC on blotter paper and in capsules was reported in late 2005. DOC is sometimes misrepresented as LSD by unscrupulous dealers. This is particularly dangerous, as DOC is not known to have the safety profile of LSD.


4-chloro-2,5-dimethoxyamphetamine is unscheduled in the United States. It is likely that it would be considered an analogue (of DOB or DOM), in which case, sales for human consumption or possession with the intent to ingest could be prosecuted under the Federal Analogue Act. In the United States, the analogues 2,5-dimethoxyamphetamine, 4-bromo-2,5-dimethoxyamphetamine, and 4-methyl-2,5-dimethoxyamphetamine are Schedule I controlled substances. DOC is scheduled in many other countries including Canada, Germany, New Zealand, Sweden and the UK.

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