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| 4-Chloro-2,5-dimethoxyamphetamine | |
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| 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 |
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| Properties | |
| Molecular formula | C11H16NO2 |
| Molar mass | 229.71 g/mol 266.17 g/mol (hydrochloride) |
| Melting point |
187-188 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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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 orally1, but some users have been known to insufflate or smoke the pure powder. It is used by some as an entheogen.
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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.
Dosage
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 10mgcitation 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 day12
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.
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-HT2A serotonin receptor, and binding affinity for the 5-HT2B and the 5-HT2C serotonin receptor.
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.
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.
Legality
DOC is unscheduled in the United States. The Department of Justice considers it to be an analogue of DOB3 and, as such, sales for human consumption or possession with the intent to ingest could be prosecuted under the Federal Analogue Act4. In the United States, the analogues DMA, DOB, and DOM are Schedule I controlled substances. DOC is scheduled in many other countries including Canada4, Australia4, Germany4, New Zealand4, United Kingdom4, and Swedencitation needed.
See also
External links
References
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Wikipedia content modification information:
- This page was last modified on 9 August 2008, at 05:07.
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