2,5-Dimethoxy-4-chloroamphetamine

2,5-Dimethoxy-4-chloroamphetamine (DOC) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was presumably first synthesized by Alexander Shulgin, and was described in his book PiHKAL (Phenethylamines i Have Known And Loved).

Chemistry
DOC is a substituted alpha-methylated phenethylamine, a class of compounds commonly known as amphetamines. The phenethylamine equivalent (lacking the alpha-methyl group) is 2C-C. DOC has a stereocenter and R-(-)-DOC is the more active stereoisomer.

Pharmacology
DOC acts as a selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist. Its psychedelic effects are mediated via its actions on the 5-HT2A receptor.

Dosage
A normal average dose of DOC ranges from 1 mg-5 mg the former producing threshold effects, and the latter producing extremely strong effects. Doses up to 10 mg 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

Effects
Unlike simple amphetamines, DOC is considered a chemical that influences cognitive and perception processes of the brain, although, to date, no authoritative source can say whether or not it is substantially psychoactive. The strongest supposed effects include open and closed eye visuals, increased awareness of sound and movement, and euphoria. In the autobiography PiHKAL, Alexander Shulgin refers to DOC as an "archetypal psychedelic" (#64); its presumed full-range visual, audio, physical, and mental effects show exhilarating clarity, and some overwhelming, humbling, and "composting"/interweaving effects. DOC in particular, apart from its longevity and potency, is highlighted for its typical sense of calm..

Dangers
The toxicity of DOC is not known, but nausea, chest pains, and vasoconstriction have been reported by some users. To date, there have been no deaths attributed to DOC.

Popularity
Although rare on the black market, sales of DOC on blotting paper and in capsules was reported in late 2005 and again in late 2007. According to the DEA December Microgram, the Concord Police Department in Contra Costa County, California, in the US, seized "a small piece of crudely lined white blotter paper without any design, suspected LSD 'blotter acid'". They added "Unusually, the paper appeared to be hand-lined using two pens, in squares measuring approximately 6 x 6 millimeters. The paper displayed fluorescence when irradiated at 365 nanometers; however, color testing for LSD with para-dimethylaminobenzaldehyde (PDMAB) was negative. Analysis of a methanol extract by GC/MS indicated not LSD but rather DOC (not quantitated but a high loading based on the TIC)". 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. It can be particularly unsafe, in comparison to LSD, for those suffering from hypertension, as phenethylamine compounds (including analogues of DOC) are known to cause sharp increases in systolic blood pressure.

Legality
DOC is unscheduled in the United States. The Department of Justice considers it to be an analogue of DOB and, as such, 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 DMA, DOB, and DOM are Schedule I controlled substances. DOC is scheduled in many other countries including Canada, Australia, Germany, New Zealand, United Kingdom, Sweden and Norway.