2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known
serotonin receptor
5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in multiple tissues including the central and peripheral nervous systems. They mediate both ex ...
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 ...
and
serotonergic psychedelic
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...
of the
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.
Effects
DOBU was first synthesized by
Alexander Shulgin
Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...
.
In his book ''
PiHKAL (Phenethylamines i Have Known And Loved)'' and other publications, he and colleagues stated that doses of 1 to 3mg
orally produced clear threshold effects and it was active at a dosage of slightly more than twice that of
DOM.
It was stated that 10mg DOBU was required to produce hallucinogenic effects.
The drug's
duration was listed as "very long".
There was limited investigation on the qualitative effects of DOAM.
However, in ''PiHKAL'', at the assessed doses of 2.2mg and 2.8mg, it was described as producing
paresthesia
Paresthesia is a sensation of the skin that may feel like numbness (''hypoesthesia''), tingling, pricking, chilling, or burning. It can be temporary or Chronic condition, chronic and has many possible underlying causes. Paresthesia is usually p ...
and difficulty
sleeping
Sleep is a state of reduced mental and physical activity in which consciousness is altered and certain Sensory nervous system, sensory activity is inhibited. During sleep, there is a marked decrease in muscle activity and interactions with th ...
with few other effects.
Pharmacology
Compared to shorter chain homologues such as
DOM,
DOET, and
DOPR which are all potent hallucinogens, DOBU has an even higher
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-HT2 receptor affinity
Affinity may refer to:
Commerce, finance and law
* Affinity (law), kinship by marriage
* Affinity analysis, a market research and business management technique
* Affinity Credit Union, a Saskatchewan-based credit union
* Affinity Equity Pa ...
.
It has been found to act as a
potent full agonist
An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the agoni ...
of the serotonin
5-HT2A and
5-HT2C receptors.
Findings are mixed with regard to the serotonin
5-HT2B receptor, with DOBU reported to act as a potent and high-
efficacy
Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as '' effectiveness'', and it has often been used synonymously, although in pharmacology a distinction is now often made betwee ...
partial agonist
In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...
of this receptor
or to be inactive as an agonist of the receptor.
DOBU fully substitutes for
DOM in rodent
drug discrimination tests, albeit several-fold less potently than
DOET or
DOPR.
In addition, DOBU robustly induces the
head-twitch response
The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...
, a behavioral proxy of
psychedelic
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...
-like effects, in rodents, and maximally does so about as strongly as other DOx drugs like DOM, DOET, and
DOC
DOC, Doc, doc or DoC may refer to:
People and characters
* Doc, an abbreviation of doctor
* Doc (nickname)
* Doc (mascot), the Towson University mascot
Persons
* The D.O.C., American rapper (born 1968)
* Doc Gallows (born 1983), ring nam ...
.
The doses at which DOBU produces peak head twitches are similar to those of DOM and DOET.
Chemistry
Isomers
Alternative
skeletal isomers of DOBU can also be produced, where the 4-(''n''-butyl) group of DOBU is replaced with any of the three other butyl isomers, the ''iso''-butyl, ''sec''-butyl and ''tert''-butyl compounds being called
DOIB,
DOSB
The German Olympic Sports Confederation (, DOSB) was founded on 20 May 2006 by a merger of the ''Deutscher Sportbund'' (DSB), and the ''Nationales Olympisches Komitee für Deutschland'' (NOK) which dates back to 1895, the year it was founded a ...
, and
DOTB, respectively.
All are significantly less potent than DOBU, with DOIB being active at around 10–15 mg, and DOSB at 25–30 mg.
The most highly branched isomer DOTB was completely inactive in both animal and human trials.
However, it was also reported that DOTB and
DOAM partially generalized to DOM in animal
drug discrimination tests.
See also
*
2,5-Dimethoxy-4-amylamphetamine (DOAM)
*
2,5-Dimethoxy-4-butylphenethylamine (2C-Bu)
References
External links
DOBU - Isomer DesignDOBU - PiHKAL - ErowidDOBU - PiHKAL - Isomer DesignHere’s What We Know About The Psychedelic DOBU - Tripsitter
{{DEFAULTSORT:Dimethoxy-4-butylamphetamine, 2,5-
5-HT2A agonists
5-HT2B agonists
5-HT2C agonists
DOx (psychedelics)
Psychedelic phenethylamines
Serotonin receptor agonists