4-Chloro-2,5-dimethoxyamphetamine
Encyclopedia
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).
alpha
-methylated phenethylamine
, a class of compounds commonly known as amphetamine
s. The phenethylamine equivalent (lacking the alpha-methyl group) is 2C-C. DOC has a stereocenter
and R-(-)-DOC is the more active stereoisomer.
, 5-HT2B
, and 5-HT2C receptor
partial agonist
. Its psychedelic effects are mediated via its actions on the 5-HT2A receptor.
" (#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..
s, and vasoconstriction
have been reported by some users. There has been at least one case of anion gap metabolic acidosis with respiratory failure requiring care in an intensive care unit following ingestion of the drug, as well as a fatality via respiritory depression currently awaiting autopsy to check for a possible drug combination interaction. To date, there have been no deaths attributed to DOC alone.
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.
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 .
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
of the phenethylamine
Substituted phenethylamine
The substituted phenethylamines are chemical compounds with the 2-phenethylamine chemical structure modified at the phenyl ring, sidechain, and/or amino group. Some of them are psychoactive drugs, including stimulants, psychedelics, opioids, and entactogens, which exert their effects primarily...
and amphetamine
Substituted amphetamine
Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...
chemical classes. It was presumably first synthesized
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
by Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
, and was described in his book PiHKAL
PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...
(Phenethylamines i Have Known And Loved).
Chemistry
DOC is a substitutedSubstituent
In organic chemistry and biochemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon...
alpha
Alpha carbon
The alpha carbon in organic chemistry refers to the first carbon that attaches to a functional group . By extension, the second carbon is the beta carbon, and so on....
-methylated phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
, a class of compounds commonly known as amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
s. The phenethylamine equivalent (lacking the alpha-methyl group) is 2C-C. DOC has a stereocenter
Stereocenter
A stereocenter or stereogenic center is an atom, bearing groups such that an interchanging of any two groups leads to a stereoisomer.A chirality center is a stereocenter consisting of an atom holding a set of ligands in a spatial arrangement which is not superposable on its mirror image...
and R-(-)-DOC is the more active stereoisomer.
Pharmacology
DOC acts as a selective 5-HT2A5-HT2A receptor
The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...
, 5-HT2B
5-HT2B receptor
5-hydroxytryptamine receptor 2B, also known as HTR2B, is a 5-HT2 receptor, but also denotes the human gene encoding it.-Function:...
, and 5-HT2C receptor
5-HT2C receptor
The 5-HT2C receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor that is coupled to Gq/G11 and mediates excitatory neurotransmission. HTR2C denotes the human gene encoding for the receptor, that in humans is located at the...
partial agonist
Partial agonist
Partial agonists bind and activate a given receptor, but have only partial efficacy at the receptor relative to a full 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 dayEffects
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 psychedelicPsychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
" (#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 painChest pain
Chest pain may be a symptom of a number of serious conditions and is generally considered a medical emergency. Even though it may be determined that the pain is non-cardiac in origin, this is often a diagnosis of exclusion made after ruling out more serious causes of the pain.-Differential...
s, and vasoconstriction
Vasoconstriction
Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels, particularly the large arteries, small arterioles and veins. The process is the opposite of vasodilation, the widening of blood vessels. The process is particularly important in...
have been reported by some users. There has been at least one case of anion gap metabolic acidosis with respiratory failure requiring care in an intensive care unit following ingestion of the drug, as well as a fatality via respiritory depression currently awaiting autopsy to check for a possible drug combination interaction. To date, there have been no deaths attributed to DOC alone.
Popularity
Although rare on the black market, sales of DOC on blotting paperBlotting paper
Blotting paper is a highly absorbent type of paper or other material. It is used to absorb an excess of liquid substances from the surface of writing paper or objects. It is also commonly used as a beauty tool to absorb excess oil from the skin.-Manufacture:Blotting paper is made from different...
and in capsules was reported in late 2005 and again in late 2007. According to the DEA
Drug Enforcement Administration
The Drug Enforcement Administration is a federal law enforcement agency under the United States Department of Justice, tasked with combating drug smuggling and use within the United States...
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 JusticeUnited States Department of Justice
The United States Department of Justice , is the United States federal executive department responsible for the enforcement of the law and administration of justice, equivalent to the justice or interior ministries of other countries.The Department is led by the Attorney General, who is nominated...
considers it to be an analogue of DOB
2,5-Dimethoxy-4-bromoamphetamine
DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967...
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
2,5-Dimethoxy-4-bromoamphetamine
DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967...
, 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 .