3,5-Dimethoxyamphetamine (3,5-DMA), also known as DMA-6, is a

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via inhal ...

of the

amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

family and a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term met ...

dimethoxyamphetamine Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and ...

(DMA). It is the

parent structure In chemistry, a parent structure is the structure of an unadorned ion or molecule from which derivatives can be visualized. Parent structures underpin systematic nomenclature and facilitate classification. Fundamental parent structures have on ...

of the 3C (4-substituted 3,5-dimethoxyamphetamine) family of compounds (also known as 3C- scalines). In an early study, it showed similar

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 Part ...

for serotonin receptors as

mescaline Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. Biological ...

(3,4,5-trimethoxyphenethylamine) but had more than an order of magnitude lower affinity than

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- positi ...

(4-substituted 2,5-dimethoxyamphetamine) drugs like DOM,

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 DOB. However, in a later study, it showed no or very low affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = >10,000nM), whereas DOB showed high affinity for these receptors (K_i = 32nM and 64nM, respectively). 3,5-DMA's effects on

monoamine Monoamine neurotransmitters are neurotransmitters and neuromodulators that contain one amino group connected to an aromatic ring by a two-carbon chain (such as -CH2-CH2-). Examples are dopamine, norepinephrine and serotonin. All monoamines ar ...

reuptake Reuptake is the reabsorption of a neurotransmitter by a neurotransmitter transporter located along the plasma membrane of an axon terminal (i.e., the pre-synaptic neuron at a synapse) or glial cell after it has performed its function of trans ...

and

efflux Efflux may refer to: * Efflux (microbiology), a mechanism responsible for moving compounds out of cells * e-flux, a publishing platform and archive See also * Efflux time, part of a measure of paint viscosity * Flux (biology) In general, flux ...

have also been studied. It appeared to be weak or inactive as a

norepinephrine reuptake inhibitor A norepinephrine reuptake inhibitor (NRI, NERI) or noradrenaline reuptake inhibitor or adrenergic reuptake inhibitor (ARI), is a type of drug that acts as a reuptake inhibitor for the neurotransmitters norepinephrine (noradrenaline) and epine ...

and

norepinephrine releasing agent A norepinephrine releasing agent (NRA), also known as an adrenergic releasing agent, is a catecholaminergic type of drug that induces the release of norepinephrine (noradrenaline) and epinephrine (adrenaline) from the pre-synaptic neuron into ...

. Likewise, it was a very weak

serotonin reuptake inhibitor A serotonin reuptake inhibitor (SRI) is a type of drug which acts as a reuptake inhibitor of the neurotransmitter serotonin (5-hydroxytryptamine, or 5-HT) by blocking the action of the serotonin transporter (SERT). This in turn leads to increa ...

( = 18,500nM) and

serotonin releasing agent A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter e ...

(active at ≥10,000nM). 3,5-DMA was inactive in substituting for DOM in rodent drug discrimination tests (4–14% appropriate responding for 5–12.5mg/kg), suggesting that it would not be

hallucinogen Hallucinogens are a large, diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Most hallucinogens can be categorized ...

ic in humans. However, it has shown other

pharmacological Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which exerts a biochemic ...

effects in mice and with similar potency as mescaline, whereas it was inactive in rats. The effects of 3,5-DMA in humans have not been reported. 3,5-DMA has been detected as an

adulterant An adulterant is caused by the act of adulteration, a practice of secretly mixing a substance with another. Typical substances that are adulterated include but are not limited to food, cosmetics, pharmaceuticals, fuel, or other chemicals, that ...

in forensic drug samples. As a

2,5-dimethoxyamphetamine Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and ...

(2,5-DMA; DMA-4), 3,5-DMA is a

Schedule I Schedule 1 may refer to: * Schedule I Controlled Substances within the US Controlled Substances Act * Schedule I Controlled Drugs and Substances within the Canadian Controlled Drugs and Substances Act * Schedule I Psychotropic Substances within th ...

controlled substance A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Sing ...

in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., federal district, five ma ...

. A derivative of 3,5-DMA,

4-bromo-3,5-dimethoxyamphetamine 4-Bromo-3,5-dimethoxyamphetamine (4-Br-3,5-DMA) is a lesser-known psychedelic drug and a substituted amphetamine. It was first synthesized by Alexander Shulgin. In his book '' PiHKAL'', the dosage range is listed as 4–10 mg and the duratio ...

(4-Br-3,5-DMA), showed relatively high affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = 210nM and 570nM, respectively). However, it was not active as a

psychedelic 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 ...

at the assessed doses (4–10mg).

References

External links

3,5-DMA - Isomer Design
{{DEFAULTSORT:Dimethoxyamphetamine, 3,5- Methoxy compounds Scalines Substituted amphetamines