2,5-Dimethoxy-4-amylamphetamine (DOAM), also known as 2,5-dimethoxy-4-pentylamphetamine, 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
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- positio ...
families.
Effects
DOAM 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 ...
orally
The word oral may refer to:
Relating to the mouth
* Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid
**Oral administration of medicines
** Oral examination (also known as an oral exam or oral ...
and the duration is unknown. DOAM was reported to produce a bare threshold and tenseness. In other publications however, DOAM has been said to produce threshold effects at 5 to 10mg orally and to be
hallucinogen
Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mo ...
ic at a dose of 40mg, with about 10-fold higher
potency
Potency may refer to:
* Potency (pharmacology), a measure of the activity of a drug in a biological system
* Virility
* Cell potency, a measure of the differentiation potential of stem cells
* In homeopathic dilutions, potency is a measure of ho ...
than
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 ...
. In any case, it shows far lower psychedelic potency than other DOx drugs such as DOM. No qualitative description of its effects at hallucinogenic doses is available.
Pharmacology
DOAM has been found to be a moderate-
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 the
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, ...
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 ...
for the serotonin 5-HT2C receptor, whereas it has very low affinity for the serotonin 5-HT1A receptor. The drug is inactive as an
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 ...
potency
Potency may refer to:
* Potency (pharmacology), a measure of the activity of a drug in a biological system
* Virility
* Cell potency, a measure of the differentiation potential of stem cells
* In homeopathic dilutions, potency is a measure of ho ...
as a human
trace amine-associated receptor 1
Trace amine-associated receptor 1 (TAAR1) is a trace amine-associated receptor (TAAR) protein that in humans is encoded by the ''TAAR1'' gene.
TAAR1 is a primarily intracellular amine-activated and G protein-coupled receptor (GPCR) that is p ...
(TAAR1) agonist. It does not bind to the
monoamine transporter
Monoamine transporters (MATs) are proteins that function as integral Cell membrane, plasma-membrane Neurotransmitter transporter, transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are se ...
drug discrimination
Drug discrimination (DD) is a technique in behavioral neuroscience used to evaluate the discriminative stimulus properties or interoceptive cues of psychoactive drugs. In drug discrimination, a subject is trained on a training drug, and then i ...
tests, producing up to 35% responding followed up behavioral disruption at higher doses. It was also unable to antagonize the DOM stimulus at the assessed doses, and behavioral disruption at higher doses prevented further assessment.
As the 4-alkyl chain length in DOx is increased from shorter homologues such as DOM,
DOET
2,5-Dimethoxy-4-ethylamphetamine (DOET) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is closely related to DOM and is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline. The ...
and
DOPR
2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It was first synthesized by Alexander Shulgin, and was described in his book ''PiHKAL'' (''Phenethylamines i Have Known And Lov ...
which are all potent hallucinogens, the serotonin 5-HT2 receptor
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 Latin ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usuall ...
increases, rising to a maximum with
DOHx
2,5-Dimethoxy-4-hexylamphetamine (DOHx or DOHE) is a non-hallucinogenic serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.
Pharmacology
DOHx has shown the highest affinity for the serotonin 5-HT2A and 5-HT2C re ...
before falling again with even longer chains. Compounds with sufficiently long chains, such as DOAM, or with bulky groups such as
DOTB
2,5-Dimethoxy-4-''tert''-butylamphetamine (DOTB or DOtBu) is a non-hallucinogenic serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.
Dosage and effects
According to Alexander Shulgin and colleagues, DOTB has bee ...
, fail to produce full psychedelic-like effects in animals and/or humans. These findings suggest that such compounds may act as low-efficacy
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 ...