2,5-Dimethoxy-4-chloroamphetamine

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2,5-Dimethoxy-4-chloroamphetamine
230px
Systematic (IUPAC) name
1-(4-chloro-2,5-dimethoxy-phenyl)propan-2-amine
Legal status
Legal status
Identifiers
CAS Number 123431-31-2
PubChem CID 542036
ChemSpider 472008
Synonyms 2,5-dimethoxy-4-chloroamphetamine
Chemical data
Formula C11H16ClNO2
Molar mass 229.70 g/mol
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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).[1]

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

File:Docpsychadelic.jpg
DOC on blotter from Concord, CA.

A normal average dose of DOC ranges from 1 mg-5 mg[2] the former producing threshold effects, and the latter producing extremely strong effects. Doses up to 10 mg[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[2][3]

Effects

Unlike simple amphetamines, DOC is a psychedelic that resembles DOB, mescaline, and other hallucinogens like LSD.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 strong and sometimes rough acting compound, with effects likened to 2C-B, high-dose LSD, or DOM. 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[citation needed], making the duration noticeably more "doable" than the similar sort of ride 2C-B, for instance, involves.

Dangers

The toxicity of DOC is not known, but nausea, chest pains, and vasoconstriction have been reported by some users. In some cases, overuse may cause permanent minor hallucinations. 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 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[4] and, as such, sales for human consumption or possession with the intent to ingest could be prosecuted under the Federal Analogue Act[5]. In the United States, the analogues DMA, DOB, and DOM are Schedule I controlled substances. DOC is scheduled in many other countries including Canada[5], Australia[5], Germany[5], New Zealand[5], United Kingdom[5], Sweden and Norway[citation needed].

See also

References

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External links


Psychedelics
5-HT2AR agonists
Lysergamides: AL-LAD • ALD-52 • BU-LAD • CYP-LAD • DAM-57 • Diallyllysergamide • Ergometrine (Ergonovine, Ergobasine) • ETH-LAD • LAE-32 • LSA (Ergine, Lysergamide) • LSD • LSH • LPD-824 • LSM-775 • Lysergic Acid 2-Butyl Amide • Lysergic Acid 2,4-Dimethylazetidide • Methylergometrine • Methylisopropyllysergamide • Methysergide • MLD-41 • PARGY-LAD • PRO-LAD;
Phenethylamines: Aleph • 2C-B • 2C-B-FLY • 2CBFly-NBOMe • 2C-C • 2C-D • 2CD-5EtO • 2C-E • 2C-F • 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-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • 2CBCB-NBOMe • 25B-NBOMe • 25I-NBMD • 25I-NBOH • 25I-NBOMe • 3C-E • 3C-P • Br-DFLY • DESOXY • DMMDA • DMMDA-2 • DOB • DOC • DOEF • DOET • DOF • DOI • DOM • DON • DOPR • DOTFM • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • IAP • Isoproscaline • Jimscaline • Lophophine • MDA • MDEA • MDMA • MMA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Methallylescaline • Proscaline • TCB-2 • TFMFly • TMA;
Piperazines: pFPP • TMFPP;
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine • 2,N,N-TMT • 4,N,N-TMT • 4-HO-5-MeO-DMT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-Acetoxy-DPT • 4-Acetoxy-MiPT • 4-HO-DPT • 4-HO-MET • 4-Propionyloxy-DMT • 4-Hydroxy-N-Methyl-(α,N-trimethylene)tryptamine • 5-Me-MIPT • 5-N,N-TMT • 5-AcO-DMT • 5-MeO-2,N,N-TMT • 5-MeO-4,N,N-TMT • 5-MeO-α,N,N-TMT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-EiPT • 5-MeO-MET • 5-MeO-MIPT • 5-Methoxy-N-methyl-(α,N-trimethylene)tryptamine • 7,N,N-TMT • α,N,N-TMT • α-ET • α-MT • AL-37350A • Baeocystin • Bufotenin • DALT • DBT • DET • DIPT • DMT • DPT • EiPT • Ethocin • Ethocybin • Iprocin • MET • Miprocin • MIPT • Norbaeocystin • PiPT • Psilocin • Psilocybin;
Others: AL-38022A • Ibogaine • Noribogaine • Voacangine
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Miscellaneous
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Others
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • D-Deprenyl • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • MMDA • MMDA-2 • Psi-DOM • TMA • TeMA
Stimulants: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • D-Deprenyl • L-Deprenyl (Selegiline)
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Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous
pl:2,5-dimetoksy-4-chloroamfetamina ru:2,5-диметокси-4-хлорамфетамин
  1. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  2. ↑ 2.0 2.1 "Erowid DOC Vault : Dosage". 
  3. ↑ "Erowid Online Books : "PiHKAL" - #64 DOC". 
  4. ↑ DEA Resources, Microgram, October 2007
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