2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known
psychedelic drug
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science ...
and a
substituted Amphetamine
Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with s ...
. DOBU was first synthesized by
Alexander Shulgin. In his book ''
PiHKAL (Phenethylamines i Have Known And Loved)'', only low dosages of 2–3 mg were tested, with the duration simply listed as "very long". DOBU produces
paresthesia and difficulty
sleeping
Sleep is a sedentary state of mind and body. It is characterized by altered consciousness, relatively inhibited Perception, sensory activity, reduced muscle activity and reduced interactions with surroundings. It is distinguished from wakefuln ...
, but with few other effects. Compared to shorter chain homologues such as
DOM,
DOET and
DOPR which are all potent hallucinogens, DOBU has an even stronger 5-HT
2 binding affinity but fails to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting it has low
efficacy and is thus an
antagonist or weak
partial agonist
In pharmacology, partial agonists are drugs that bind to and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonist ...
at the 5-HT
2A receptor.
Isomers
Alternative 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 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, and both being primarily stimulant in action with little or no psychedelic effects. The most highly branched isomer DOTB was completely inactive in both animal and human trials.
See also
*
2,5-Dimethoxy-4-Substituted Amphetamine
4-Substituted-2,5-dimethoxyamphetamines (DO''x'') is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of ...
s
References
External links
DOBU Entry in ''PiHKAL''DOBU Entry in PiHKAL • info
{{DEFAULTSORT:Dimethoxy-4-butylamphetamine, 2,5-
Substituted amphetamines