2,5-Dimethoxy-4-chloroamphetamine (DOC) is a
psychedelic drug
A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...
of the
phenethylamine,
amphetamine
Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...
, and
DOx families. It was presumably first
synthesized by
Alexander Shulgin, and was described in his book ''
PiHKAL
''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...
'' (''Phenethylamines i Have Known And Loved'').
Chemistry
DOC is a
substituted alpha
Alpha (uppercase , lowercase ) is the first letter of the Greek alphabet. In the system of Greek numerals, it has a value of one. Alpha is derived from the Phoenician letter ''aleph'' , whose name comes from the West Semitic word for ' ...
-
methylated
phenethylamine, a class of compounds commonly known as
amphetamine
Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...
s. The phenethylamine equivalent (lacking the alpha-methyl group) is
2C-C
2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', Shulgin lists the dosage range as 20–40 mg. 2C- ...
. DOC has a
stereocenter
In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups cr ...
and (''R'')-(−)-DOC is the more active
stereoisomer.
Pharmacology
Pharmacodynamics
Actions
DOC acts as a
serotonin
Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
5-HT2A and
5-HT2C receptor agonist
An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...
. Its psychedelic effects are mediated via its actions on the 5-HT
2A receptor.
The drug is inactive as a
monoamine releasing agent and
reuptake inhibitor.
Effects
DOC produces the
head-twitch response, a behavioral proxy of
psychedelic-like effects, in rodents.
DOC has shown
reinforcing effects, including
conditioned place preference (CPP) and
self-administration
Self-administration is, in its Medicine, medical sense, the process of a subject administering a Pharmacology, pharmacological substance to themself. A clinical example of this is the subcutaneous "self-injection" of insulin by a Diabetes, diabetic ...
, in rodents similarly to
methamphetamine
Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug use, recreational or Performance-enhancing substance, performance-enhancing drug and less commonly as a secon ...
.
This is analogous to other findings in which various
2C and
NBOMe
The 25-NB (25''x''-NB''x'') series, or NBOMe series, also known as the ''N''-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C (psychedelics), 2C family. The most c ...
drug
A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...
s have been found to produce
dopaminergic
Dopaminergic means "related to dopamine" (literally, "working on dopamine"), a common neurotransmitter. Dopaminergic substances or actions increase dopamine-related activity in the brain.
Dopaminergic pathways, Dopaminergic brain pathways facil ...
elevations and reinforcing effects in rodents.
Conversely however, in contrast to
amphetamine
Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...
s like
(–)-cathinone but similarly to
mescaline
Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...
,
DOM has shown no
stimulant
Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...
-like or reinforcing effects in
rhesus monkey
The rhesus macaque (''Macaca mulatta''), colloquially rhesus monkey, is a species of Old World monkey. There are between six and nine recognised subspecies split between two groups, the Chinese-derived and the Indian-derived. Generally brown or g ...
s.
Interactions
Dosage
A normal average dose of DOC ranges from 0.2–7.0
mg the former producing threshold effects, and the latter producing extremely strong effects. Onset of the drug is 1–3 hours, peak and plateau at 4–8 hours, and a gradual come down with residual stimulation at 9-20h. 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. The strongest supposed effects include open and
closed eye visuals, increased awareness of sound and movement, and euphoria. In the autobiography PiHKAL, Alexander Shulgin included a description of DOC as "an
archetypal
The concept of an archetype ( ) appears in areas relating to behavior, History of psychology#Emergence of German experimental psychology, historical psychology, philosophy and literary analysis.
An archetype can be any of the following:
# a stat ...
psychedelic" (#64); its presumed full-range visual, audio, physical, and mental effects show exhilarating clarity, and some overwhelming, humbling, and "composting"/interweaving effects.
Dangers
Very little data exists about the toxicity of DOC. In April 2013, a case of death due to DOC was reported. The source does not specify whether the drug alone caused the death. In 2014, a death was reported in which DOC was directly implicated as the sole causative agent in the death of a user. The autopsy indicated
pulmonary edema
Pulmonary edema (British English: oedema), also known as pulmonary congestion, is excessive fluid accumulation in the tissue or air spaces (usually alveoli) of the lungs. This leads to impaired gas exchange, most often leading to shortness ...
and a
subgaleal hemorrhage.
Detection in biological specimens
DOC may be quantitated in blood, plasma or urine by gas chromatography-mass spectrometry or liquid chromatography-mass spectrometry to confirm a diagnosis of poisoning in hospitalized patients or to provide evidence in a medicolegal death investigation. Blood or plasma DOC concentrations are expected to be in a range of 1–10 μg/L in persons using the drug recreationally, >20 μg/L in intoxicated patients and >100 μg/L in victims of acute overdosage.
Popularity
Although rare on the
black market
A black market is a Secrecy, clandestine Market (economics), market or series of transactions that has some aspect of illegality, or is not compliant with an institutional set of rules. If the rule defines the set of goods and services who ...
, it has been available in bulk and shipped worldwide by select elite "Grey Market" Research Chemical suppliers for several years. Sales of DOC on
blotting paper and in capsules was reported in late 2005 and again in late 2007. According to the
DEA's Microgram from December 2007, 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 (
Ehrlich's reagent) 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
Hypertension, also known as high blood pressure, is a Chronic condition, long-term Disease, medical condition in which the blood pressure in the artery, arteries is persistently elevated. High blood pressure usually does not cause symptoms i ...
, as amphetamine compounds are known to cause sharp increases in systolic
blood pressure
Blood pressure (BP) is the pressure of Circulatory system, circulating blood against the walls of blood vessels. Most of this pressure results from the heart pumping blood through the circulatory system. When used without qualification, the term ...
.
Drug prohibition laws
Canada
Listed as a
Schedule 1 as it is an analogue of amphetamine.
The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.
Australia
Unscheduled but can be controlled as schedule II as an analogue of DOB.
China
As of October 2015 DOC is a controlled substance in China.
New Zealand
Scheduled.
Denmark
Denmark added DOC to the list of Schedule I controlled substances as of 8.4.2007.
Germany
Scheduled in Anlage I since 22.1.2010.
Sweden
''Sveriges riksdag'' added DOC to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as narcotics in Sweden as of Aug 30, 2007, published by
''Medical Products Agency'' in their regulation LVFS 2007:10 listed as DOC, 4-klor-2,5-dimetoxi-amfetamin.
DOC was first classified by
''Sveriges riksdags'' health ministry
''Statens folkhälsoinstitut'' as "health hazard" under the act
''Lagen om förbud mot vissa hälsofarliga varor'' (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') as of Jul 1, 2004, in their regulation SFS 2004:486 listed as 4-klor-2,5-dimetoxiamfetamin (DOC).
United Kingdom
Class A.
United States
DOC is not scheduled or controlled at the federal level in the
United States
The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...
,
but the
Department of Justice considers it to be an analogue of
DOB and, as such, possession or sale could be prosecuted under the
Federal Analogue Act.
In December 2023, the US
Drug Enforcement Administration
The Drug Enforcement Administration (DEA) is a Federal law enforcement in the United States, United States federal law enforcement agency under the U.S. Department of Justice tasked with combating illicit Illegal drug trade, drug trafficking a ...
issued a
notice of proposed rulemaking that would classify both 2,5-dimethoxy-4-chloroamphetamine and
2,5-dimethoxy-4-iodoamphetamine as schedule I controlled substances.
In the United States, the analogues
DMA,
DOB, and
DOM are Schedule I
controlled substances.
US State of Florida
DOC is a Schedule I
controlled substance in the state of
Florida
Florida ( ; ) is a U.S. state, state in the Southeastern United States, Southeastern region of the United States. It borders the Gulf of Mexico to the west, Alabama to the northwest, Georgia (U.S. state), Georgia to the north, the Atlantic ...
making it illegal to buy, sell, or possess.
United Nations
In December 2019, the
UNODC announced scheduling recommendations placing DOC into Schedule I alongside another several
research chemicals.
See also
*
2,5-Dimethoxy-4-Substituted Amphetamines
*
DODC
*
ZDCM-04
References
External links
DOC - Isomer DesignDOC - PsychonautWikiDOC - ErowidDOC - PiHKAL - ErowidDOC - PiHKAL - Isomer DesignDOC (4-Chloro-2,5-Dimethoxyamphetamine): Everything You Need to Know - Tripsitter
{{DEFAULTSORT:Dimethoxy-4-chloroamphetamine, 2,5-
5-HT2A agonists
5-HT2B agonists
5-HT2C agonists
Chlorobenzene derivatives
Designer drugs
DOx (psychedelics)
Psychedelic phenethylamines