MMDA, also known as 3-methoxy-4,5-methylenedioxyamphetamine or as 5-methoxy-MDA, is a

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 ...

and

entactogen Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observe ...

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 ...

family.

Use and effects

MMDA was described 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 ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

''. Shulgin lists the dosage range of MMDA as 100 to 250mg. The first effects appear within 20 to 45minutes following

oral administration Oral administration is a route of administration whereby a substance is taken through the Human mouth, mouth, swallowed, and then processed via the digestive system. This is a common route of administration for many medications. Oral administ ...

. Its duration is described as "moderate". MMDA produces effects including relaxation,

time dilation Time dilation is the difference in elapsed time as measured by two clocks, either because of a relative velocity between them (special relativity), or a difference in gravitational potential between their locations (general relativity). When unsp ...

empathy Empathy is generally described as the ability to take on another person's perspective, to understand, feel, and possibly share and respond to their experience. There are more (sometimes conflicting) definitions of empathy that include but are ...

, passivity,

compassion Compassion is a social feeling that motivates people to go out of their way to relieve the physical, mental, or emotional pains of others and themselves. Compassion is sensitivity to the emotional aspects of the suffering of others. When based ...

, changes in

music Music is the arrangement of sound to create some combination of Musical form, form, harmony, melody, rhythm, or otherwise Musical expression, expressive content. Music is generally agreed to be a cultural universal that is present in all hum ...

perception,

closed-eye visual Closed-eye hallucinations and closed-eye visualizations (CEV) are hallucinations that occur when one's eyes are closed or when one is in a darkened room. They should not be confused with phosphenes, perceived light and shapes when pressure is ap ...

s such as geometric patterns,

open-eye visual A visual hallucination is a vivid visual experience occurring without corresponding external stimuli in an awake state. These experiences are involuntary and possess a degree of perceived reality sufficient to resemble authentic visual perception. ...

dream A dream is a succession of images, ideas, emotions, and sensation (psychology), sensations that usually occur involuntarily in the mind during certain stages of sleep. Humans spend about two hours dreaming per night, and each dream lasts around ...

-like states described as "brain movies", and an

afterglow An afterglow in meteorology consists of several atmospheric optical phenomena, with a general definition as a broad arch of whitish or pinkish sunlight in the twilight sky, consisting of the bright segment and the purple light. Purple light mai ...

. It has been said to be gentler than certain other psychedelics. The drug is said to have similar effects to

MDA MDA, mda or variants may refer to: Businesses and organizations Political parties * Meghalaya Democratic Alliance (2003–2008), in India * Meghalaya Democratic Alliance (2018–present), in India * Movement for Democracy in Africa, in Burkina F ...

, but to be to some extent more psychedelic in comparison.

Side effects

Side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...

s of MMDA have been reported to include restlessness, cold sensations,

shivering Shivering (also called shuddering) is a bodily function in response to cold and extreme fear in warm-blooded animals. When the core body temperature drops, the shivering reflex is triggered to maintain homeostasis. Skeletal muscles begin to sha ...

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...

, abdominal cramps,

disorientation Orientation is a function of the mind involving awareness of three dimensions: time, place and person. Problems with orientation lead to ''dis''orientation, and can be due to various conditions. It ranges from an inability to coherently understand ...

social withdrawal Solitude, also known as social withdrawal, is a state of seclusion or isolation, meaning lack of socialisation. Effects can be either positive or negative, depending on the situation. Short-term solitude is often valued as a time when one may w ...

, feeling ill, and

anxiety Anxiety is an emotion characterised by an unpleasant state of inner wikt:turmoil, turmoil and includes feelings of dread over Anticipation, anticipated events. Anxiety is different from fear in that fear is defined as the emotional response ...

Interactions

Pharmacology

Pharmacodynamics

MMDA has been shown to act as a non-

neurotoxic Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specifical ...

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 ...

, with no effects on release of

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

or probably

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

, and as a

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-HT_2A receptor

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 ...

. The latter property is thought to be responsible for its

effects, whereas the former action may be involved in its

ic effects.

Pharmacokinetics

MMDA has been found to be formed from

myristicin Myristicin is a naturally occurring compound (an allylbenzene) found in common herbs and spices such as nutmeg. It is an insecticide, and has been shown to enhance the effectiveness of other insecticides. When ingested in high doses, myristicin ...

, a component of

nutmeg Nutmeg is the seed, or the ground spice derived from the seed, of several tree species of the genus '' Myristica''; fragrant nutmeg or true nutmeg ('' M. fragrans'') is a dark-leaved evergreen tree cultivated for two spices derived from its fru ...

, in rabbits and rats. However, MMDA could not be detected with nutmeg misuse in a human.

Chemistry

Analogues of MMDA include

lophophine Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA), is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related t ...

(MMDPEA),

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used ...

, and

TMA TMA may refer to: Science * Tense–Modality–Aspect or ''tense–aspect–mood'', grammatical system * Tetramethylammonium ion or its salts * Thermomechanical analysis * Third man argument, a philosophical criticism of Plato's theory of Form ...

Positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

s of MMDA include

MMDA-2 MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the amphetamine class. It is closely related to MMDA and MDA. Alexander Shulgin was likely the first to synthesize MMDA-2. In his book ...

MMDA-3a MMDA-3a, also known as 2-methoxy-3,4-methylenedioxyamphetamine or as 2-methoxy-MDA, is a psychedelic drug of the amphetamine family. It is the 2-methoxy derivative of 3,4-methylenedioxyamphetamine (MDA). The drug produces hallucinogenic effects i ...

MMDA-3b MMDA, also known as 3-methoxy-4,5-methylenedioxyamphetamine or as 5-methoxy-MDA, is a psychedelic and entactogen of the amphetamine family. Use and effects MMDA was described by Alexander Shulgin in his book ''PiHKAL''. Shulgin lists the dosage ...

, MMDA-4, and MMDA-5. Further analogues and

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

s of MMDA include

DMMDA 2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA or DMMDA-1) is a lesser-known psychedelic drug of the amphetamine family related to MMDA. It was first synthesized by Alexander Shulgin in the 1960s and was described in his 1991 book ''PiHKAL ...

DMMDA-2 DMMDA-2 is a bioactive phenethylamine discussed by Alexander Shulgin in his book '' PiHKAL (Phenethylamines i Have Known And Loved)''; however, he was not the first to synthesize it. Shulgin comments in his book that a 50 milligram dose of DMMDA ...

, DMMDA-3, DMMDA-4, DMMDA-5, and DMMDA-6.

History

MMDA was first synthesized and studied by

Gordon Alles Gordon A. Alles (November 26, 1901 – January 21, 1963), was an American chemist and pharmacologist who did extensive research on the isolation and properties of insulin for the treatment of diabetes, diabetics. He is also credited with discoveri ...

at the

Edgewood Arsenal Aberdeen Proving Ground (APG) is a U.S. Army facility located adjacent to Aberdeen, Harford County, Maryland, United States. More than 7,500 civilians and 5,000 military personnel work at APG. There are 11 major commands among the tenant units, ...

in the mid-1950s. Its Edgewood Arsenal code name is unknown. Subsequently,

synthesized MMDA in 1962 and discovered its

psychoactive effect A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...

s that same year. Shulgin published his findings on MMDA in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

in 1964. Use of MMDA in psychedelic-assisted psychotherapy was studied by Shulgin, Thornton Sargent, and

Claudio Naranjo Claudio Benjamín Naranjo Cohen (24 November 1932 – 12 July 2019) was a Chilean psychiatrist who is considered a pioneer in integrating psychotherapy and the spiritual traditions. He was one of the three successors named by Fritz Perls (foun ...

in the mid-1960s and their findings were published in 1973. Naranjo also described MMDA for these purposes in his 1973 book ''The Healing Journey: New Approaches to Consciousness''. Shulgin subsequently further described MMDA in his book ''

'' in 1991.

Society and culture

Legal status

International

Internationally, MMDA is a Schedule I drug under the

Convention on Psychotropic Substances The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamine-type stimulants, barbiturates, benzodiazepines, and psychedelics signed in Vienna, Austria on 21 February ...

Australia

MMDA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534 A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.

United States

MMDA is classified as a Schedule 1 substance in the United States, and is similarly controlled in other parts of the world. MMDA remains illegal, however it is classified differently than the illegality of MDMA.

References

External links

MMDA - Isomer Design

MMDA - PiHKAL - Erowid

MMDA - PiHKAL - Isomer Design
{{DEFAULTSORT:Methoxy-4,5-methylendioxyamphetamine, 3- 5-HT2A agonists Alexander Shulgin Designer drugs Entactogens Methoxyphenethylamines Methylenedioxyphenethylamines Phenol ethers Psychedelic phenethylamines Serotonin receptor agonists Serotonin releasing agents Substituted amphetamines