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 o ...

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 sub ...

. DOBU was first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamph ...

. 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 Paresthesia is an abnormal sensation of the skin (tingling, pricking, chilling, burning, numbness) with no apparent physical cause. Paresthesia may be transient or chronic, and may have any of dozens of possible underlying causes. Paresthesias ar ...

and difficulty

sleeping Sleep is a sedentary state of mind and body. It is characterized by altered consciousness, relatively inhibited sensory activity, reduced muscle activity and reduced interactions with surroundings. It is distinguished from wakefulness by a de ...

, but with few other effects. Compared to shorter chain homologues such as

DOM Dom or DOM may refer to: People and fictional characters * Dom (given name), including fictional characters * Dom (surname) * Dom La Nena (born 1989), stage name of Brazilian-born cellist, singer and songwriter Dominique Pinto * Dom people, an et ...

DOET 2,5-Dimethoxy-4-ethylamphetamine (DOET, DOE, Hecate) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book '' PiHKAL'' (''Phenethylamines i Hav ...

and

DOPR 2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was a ...

which are all potent hallucinogens, DOBU has an even stronger 5-HT₂

binding affinity In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usually a mol ...

but fails to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting it has low

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 pragmatic clinical trial#Efficacy versu ...

and is thus an

antagonist An antagonist is a character in a story who is presented as the chief foe of the protagonist. Etymology The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, riv ...

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 antagonistic e ...

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.

References

External links

DOBU Entry in ''PiHKAL''

DOBU Entry in PiHKAL • info
{{DEFAULTSORT:Dimethoxy-4-butylamphetamine, 2,5- Substituted amphetamines

Isomers

See also

References

External links