4-Chloro-2,5-dimethoxyamphetamine

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4-Chloro-2,5-dimethoxyamphetamine

IUPAC name	2-(4-Chloro-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
Other names	4-Chloro-2,5-dimethoxy-amphetamine 1-(4-Chloro-2,5-dimethoxyphenyl)-2-aminopropane
Identifiers
CAS number
SMILES	COc1cc(C[C@@H](C)N)c(cc1Cl)OC
Properties
Molecular formula	C₁₁H₁₆NO₂
Molar mass	229.71 g/mol 266.17 g/mol (hydrochloride)
Melting point	187-188 °C 193-194.5 °C (hydrochloride)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

DOC or 2,5-dimethoxy-4-chloroamphetamine is a potent psychedelic amphetamine. DOC was presumably first synthesized by Alexander Shulgin. The drug is generally taken orally^[1], but some users have been known to insufflate or smoke the pure powder. It is used by some as a entheogen.

1 Chemistry
2 Dosage
3 Effects
4 Pharmacology
5 Dangers
6 Popularity
7 Legality
8 See also
9 External links
10 References

[edit] Chemistry

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

[edit] Dosage

DOC on blotter from Concord, CA.

A normal average dose of DOC ranges from 1mg-5mg ^[1] the former producing threshold effects, and the latter producing extremely strong effects. Doses up to 10mg^{[citation needed]} 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^[1]^[2]

[edit] Effects

Unlike simple amphetamines, DOC is a psychedelic that resembles LSD, DOB, and mescaline.These effects include open and closed eye visuals, increased awareness of sound and movement and euphoria. Its properties as an amphetamine are dwarfed by its unmistakable and potent properties as the "heavy-weight champ" of the Shulgin synthetic phenethylamine discoveries, with effects likened to 2C-B, high-dose LSD or DOM, and batting well into class 3-4 territory by Shulgin ratings at the 5mg level. In PiHKAL, Shulgin describes it as an archetypal psychedelic (#64); its full-range visual, audio, physical and mental effects share some of the exhilarating clarity of high-dose LSD, and some of the overwhelming, humbling and "composting"/interweaving effect of high-dose mescaline. It is often praised in particular, apart from its longevity and potency, for its typical sense of calm and relative ease, making the duration noticeably more "doable" than the similar sort of ride 2C-B, for instance, involves.

[edit] Pharmacology

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-HT_2A serotonin receptor, and binding affinity for the 5-HT_2B and the 5-HT_2C serotonin receptor.

[edit] Dangers

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.

[edit] 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 4-chloro-2,5-dimethoxyamphetamine (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.

[edit] Legality

DOC is unscheduled in the United States. The Department of Justice considers it to be an analogue of DOB^[3] and, as such, sales for human consumption or possession with the intent to ingest could be prosecuted under the Federal Analogue Act^[4]. In the United States, the analogues DMA, DOB, and DOM are Schedule I controlled substances. DOC is scheduled in many other countries including Canada^[4], Australia^[4], Germany^[4], New Zealand^[4], United Kingdom^[4], and Sweden^{[citation needed]}.