MDAI

Last updated

MDAI
MDAI.svg
MDAI 3D ball.png
Clinical data
Other names5,6-Methylenedioxy-2-aminoindane; 5,6-Methylenedioxy-2-aminoindan; Methylenedioxyaminoindane; Methylenedioxyaminoindan
Routes of
administration 		Oral [1]
Drug class Serotonin–norepinephrine releasing agent; [2] Entactogen [1]
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action 2–6 hours [4] [1]
Identifiers
  • 6,7-Dihydro-5H-cyclopenta[f] [1,3]benzodioxol-6-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C10H11NO2
Molar mass 177.203 g·mol−1
3D model (JSmol)
  • C1C(CC2=CC3=C(C=C21)OCO3)N
  • InChI=1S/C10H11NO2/c11-8-1-6-3-9-10(13-5-12-9)4-7(6)2-8/h3-4,8H,1-2,5,11H2 Yes check.svgY
  • Key:FQDRMHHCWZAXJM-UHFFFAOYSA-N Yes check.svgY

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects. [4] [5] [6] [1]

Contents

It acts as a selective serotonin and norepinephrine releasing agent (SNRA). [2] The drug shows greatly reduced serotonergic neurotoxicity in comparison to MDMA in animals, although it still shows weak capacity for neurotoxicity with chronic use or in combination with amphetamine. [7] [8] [9]

MDAI was developed in the 1990s by a team led by David E. Nichols at Purdue University. [10] It has been encountered as a designer drug and has been used recreationally with reported street names such as "sparkle" and "mindy". [5] [11] [7] [6] In addition to its recreational use, there has been interest in MDAI for potential use in medicine, for instance in drug-assisted psychotherapy. [4]

Uses

Scientific research

MDAI and other similar drugs have been widely used in scientific research, as they are able to replicate many of the effects of MDMA, but without causing the serotonergic neurotoxicity associated with MDMA and certain related drugs. No tests have been performed on cardiovascular toxicity. [12] [13] [14] [15] [16] [17] [18]

Recreational drug

MDAI has been advertised as a designer drug. It started to be sold online from around 2007, but reached peak popularity between about 2010 to 2012, after bans on mephedrone came into effect in various countries. Internet-sourced products claimed to be MDAI have been shown variously to contain mephedrone or other substituted cathinone derivatives, and mixed compositions of inorganic substances, while generally containing no MDAI. The number of internet searches for MDAI has been considerably higher in the United Kingdom compared to Germany and the United States. [11] MDAI is only non-neurotoxic in isolation but may become neurotoxic when mixed with other drugs. [19] Three deaths were linked to MDAI use in the UK during 2011–2012, all involving symptoms consistent with serotonin syndrome. Two of these also involved other drugs while one death appeared to be from MDAI alone. [7]

Pharmacology

Pharmacodynamics

MDAI acts as a selective and well-balanced serotonin and norepinephrine releasing agent (SNRA) with much less (~10-fold lower) effect on dopamine release. [2] In addition to inducing the release of the monoamine neurotransmitters, MDAI also inhibits their reuptake. [10] For comparison to MDAI, MDA and MDMA are well-balanced releasing agents of serotonin, norepinephrine, and dopamine (SNDRAs). [2] Conversely, the profile of monoamine release with MDAI is very similar to that of (R)-MDMA (levo-MDMA), which like MDAI is also a well-balanced SNRA with about 10-fold reduced impact on dopamine release, though MDAI is several-fold more potent than (R)-MDMA in vitro . [20] [2]

In contrast to MDMA, MDAI shows no affinity for any of the serotonin receptors (Ki = all >10 μM). [2] This notably includes the serotonin 5-HT2A receptor, which is implicated in producing psychedelic effects, and the serotonin 5-HT2B receptor, which is implicated in causing cardiac valvulopathy. [2] [21] However, MDAI shows significant affinity for all three of the α2-adrenergic receptors (Ki = 322 to 1121 nM). [2]

Activities of MDAI and related drugs
Compound Monoamine release (EC50 Tooltip half-maximal effective concentration, nM)
Serotonin Norepinephrine Dopamine
2-AI >1000086439
MDAI 1141171334
MMAI 313101>10000
MEAI 1348612646
Dextroamphetamine 698–17656.6–7.25.8–24.8
Dextromethamphetamine 736–1291.712.3–13.88.5–24.5
MDA 160108190
MDMA 49.6–7254.1–11051.2–278
  (R)-MDMA (levo-MDMA)3405603700
MDEA 472608622
MBDB 5403300>100000
Notes: The smaller the value, the more strongly the compound produces the effect. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: [2] [22] [23] [24] [25] [26] [27]

Effects

The family of drugs typified by MDMA produce their effects through multiple mechanisms of action in the body, and consequently produce three distinct cues which animals can be trained to respond to: a stimulant cue typified by drugs such as methamphetamine, a psychedelic cue typified by drugs such as LSD and DOM, and an "entactogen-like" cue which is produced by drugs such as MDAI and MBDB. These drugs cause drug-appropriate responses in animals trained to recognize the effects of MDMA, but do not produce responses in animals trained selectively to respond to stimulants or hallucinogens. Because these compounds selectively release serotonin in the brain but have little effect on dopamine or noradrenaline levels, they can produce empathogenic effects but without any stimulant action, instead being somewhat sedating. [28] [29] [30] [31] [32] [33] [34]

A 2024 study compared the effects of MDAI and MDMA in humans. [1] It found that MDAI produced comparable and very similar subjective effects to those of MDMA. [1] This included pleasurable drug effects, drug liking, stimulation, happiness, openness, trust, and closeness. [1] In addition, it included sense of well-being, emotional excitation, and extroversion, but not general activity or concentration, a profile of effects described as similar to that of MDMA. [1] Other effects included a blissful state, experience of unity, and changed meaning of percepts, also described as comparable to MDMA. [1] The effects of MDAI were slightly greater than those of 75 mg MDMA and slightly lower than those of 125 mg MDMA. [1] At the employed dose of 3.0 mg/kg, with 125 mg MDMA corresponding to 1.9 mg/kg, it was estimated that MDAI had about 60% of MDMA's potency in producing comparable psychoactive effects (hence, roughly 200 mg MDAI would be similar to 125 mg MDMA). [1] Aside from subject effects, MDAI also increased blood pressure, cortisol levels, and prolactin levels similarly to MDMA. [1] Conversely, it did not increase heart rate or body temperature. [1]

Neurotoxicity

MDAI shows substantially lower serotonergic neurotoxicity than MDMA in animals and has been described as a "non-neurotoxic" analogue of MDMA. [7] [8] [9] However, MDAI still shows weak serotonergic neurotoxicity both alone and particularly in combination with amphetamine in animals. [7] [8] [9] As such, MDAI does not appear to be a fully non-neurotoxic alternative to MDMA. [7] [8] [9]

Toxicity

Very high doses can be fatal in rats with a 50% fatality rate for those subcutaneously injected with 28 mg/kg of MDAI. This is a result of the way serotonin release interferes with thermoregulation. [35]

Pharmacokinetics

The duration of MDAI in humans appears to be similar to that of MDMA at 2 to 5 hours [4] or up to around 6 hours. [1]

Chemistry

MDAI in powder form. MDAI.jpg
MDAI in powder form.

The chemical structure of MDAI is indirectly derived from that of the illicit drug MDA, but the α-methyl group of the alkyl amino amphetamine side chain has been bound back to the benzene nucleus to form an indane ring system, which changes its pharmacological properties substantially.

Analogues

Synthesis

MDAI can be produced from 3-(3,4-methylenedioxyphenyl)propionic acid [12] which is converted to the acid chloride and then heated to produce 5,6-methylenedioxy-1-indanone. Treatment of the indanone with amyl nitrite in methanol with HCl afforded the hydroxyimino ketone. This is reduced to the 2-aminoindan following a modification of Nichols' earlier method from a paper discussing DOM analogues, [36] using a Pd/C catalyst in glacial acetic acid with catalytic H2SO4.

Society and culture

China

As of October 2015 MDAI is a controlled substance in China. [37]

Denmark

MDAI is illegal in Denmark as of September 2015. [38]

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market". [39]

Switzerland

As of December 2011 MDAI is a controlled substance in Switzerland. [40]

Related Research Articles

<span class="mw-page-title-main">Empathogen</span> Class of psychoactive drugs that produce empathic experiences

Empathogens or entactogens are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, relatedness, emotional openness—that is, empathy or sympathy—as particularly observed and reported for experiences with 3,4-methylenedioxymethamphetamine (MDMA). This class of drug is distinguished from the classes of hallucinogen or psychedelic, and amphetamine or stimulants. Major members of this class include MDMA, MDA, MDEA, MDOH, MBDB, 5-APB, 5-MAPB, 6-APB, 6-MAPB, methylone, mephedrone, GHB, αMT, and αET, MDAI among others. Most entactogens are phenethylamines and amphetamines, although several, such as αMT and αET, are tryptamines. When referring to MDMA and its counterparts, the term MDxx is often used. Entactogens are sometimes incorrectly referred to as hallucinogens or stimulants, although many entactogens such as ecstasy exhibit psychedelic or stimulant properties as well.

α-Ethyltryptamine Chemical compound

α-Ethyltryptamine, also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before being withdrawn due to toxicity.

<span class="mw-page-title-main">MBDB</span> Chemical compound

MBDB, also known as N-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is an entactogen of the phenethylamine, amphetamine, and phenylisobutylamine families related to MDMA. It is known by the street names "Eden" and "Methyl-J".

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

<span class="mw-page-title-main">5-APDB</span> Chemical compound

5-(2-Aminopropyl)-2,3-dihydrobenzofuran is a putative entactogen drug of the phenethylamine and amphetamine classes. It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge. 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead. 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues of MDMA.

<span class="mw-page-title-main">Monoamine releasing agent</span> Class of compounds

A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; monoamine releasing agents can induce the release of one or more of these neurotransmitters.

<span class="mw-page-title-main">3-Methoxy-4-methylamphetamine</span> Entactogen and psychedelic drug of the phenethylamine and amphetamine classes

3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s.

<span class="mw-page-title-main">MMAI</span> Chemical compound

5-Methoxy-6-methyl-2-aminoindane (MMAI) is a drug of the 2-aminoindane group developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a less neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogenic effects in humans. It has been sold as a designer drug and research chemical online since 2010.

<span class="mw-page-title-main">MDMAI</span> Chemical compound

5,6-Methylenedioxy-N-methyl-2-aminoindane (MDMAI), is a drug of the 2-aminoindane group developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in animals and a putative entactogen in humans.

<span class="mw-page-title-main">5-IAI</span> Chemical compound

5-Iodo-2-aminoindane (5-IAI) is an entactogen drug of the 2-aminoindane group. Human anecdotal reports suggest that it is entactogenic but produces little euphoria or stimulation.

<span class="mw-page-title-main">Serotonin releasing agent</span> Class of compounds

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 efflux at other types of monoamine neurons, including dopamine and norepinephrine neurons.

α-Methyldopamine Chemical compound

α-Methyldopamine (α-Me-DA), also known as 3,4-dihydroxyamphetamine or as catecholamphetamine, is a research chemical of the catecholamine and amphetamine families. It is a monoamine releasing agent and a metabolite of MDMA and MDA. The bis-glutathionyl metabolite of α-methyldopamine is slightly neurotoxic when directly injected into the brain's ventricles.

<span class="mw-page-title-main">MDAT</span> Chemical compound

6,7-Methylenedioxy-2-aminotetralin (MDAT) is a drug developed in the 1990s by a team at Purdue University led by David E. Nichols. It appears to act as a serotonin releasing agent based on rodent drug discrimination assays comparing it to MDMA, in which it fully substitutes for, and additionally lacks any kind of serotonergic neurotoxicity. Hence, MDAT is considered likely to be a non-neurotoxic, putative entactogen in humans.

<span class="mw-page-title-main">6-CAT</span> Chemical compound

6-Chloro-2-aminotetralin (6-CAT) is a drug which acts as a selective serotonin releasing agent (SSRA) and is a putative entactogen in humans. It is a rigid analogue of para-chloroamphetamine (PCA).

<span class="mw-page-title-main">MDMAT</span> Selective serotonin releasing agent and psychoactive drug

MDMAT (6,7-methylenedioxy-N-methyl-2-aminotetralin) is a selective serotonin releasing agent (SSRA) and entactogen drug. It is the N-methylated derivative of MDAT, similarly to the relationship of MDMA to MDA. It has been theorized to have less long-term neurotoxicity and less hallucinogenic effects than other MDxx derivatives, but no formal scientific research has been conducted specifically on MDMAT.

<span class="mw-page-title-main">4-Chlorophenylisobutylamine</span> Entactogen and stimulant drug of the phenethylamine class

4-Chlorophenylisobutylamine, also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine, amphetamine, and phenylisobutylamine families. It is an analogue of para-chloroamphetamine (PCA) where the alpha position methyl has been replaced with an ethyl group.

<span class="mw-page-title-main">5-MAPB</span> Chemical compound

5-MAPB, also known as 5-(N-methyl-2-aminopropyl)benzofuran, is an entactogen and designer drug of the amphetamine family that is similar to MDMA in its structure and effects.

<span class="mw-page-title-main">Monoamine neurotoxin</span> Compounds that damage or destroy monoaminergic neurons

A monoamine neurotoxin, or monoaminergic neurotoxin, is a drug that selectively damages or destroys monoaminergic neurons. Monoaminergic neurons are neurons that signal via stimulation by monoamine neurotransmitters including serotonin, dopamine, and norepinephrine.

(<i>R</i>)-MDMA Psychoactive drug taken by mouth

(R)-3,4-Methylenedioxy-N-methylamphetamine ((R)-MDMA), also known as (R)-midomafetamine or as levo-MDMA, is the (R)- or levorotatory (l-) enantiomer of 3,4-methylenedioxy-N-methylamphetamine (MDMA; midomafetamine; "ecstasy"), a racemic mixture of (R)-MDMA and (S)-MDMA. Like MDMA, (R)-MDMA is an entactogen or empathogen. It is taken by mouth.

<span class="mw-page-title-main">Borax combo</span> Designer drug combination mimicking MDMA

The Borax combo, also known by the informal brand names Blue Bliss and Pink Star, is a combination recreational and designer drug described as an MDMA-like entactogen.

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  39. ↑ https://finlex.fi/fi/laki/ajantasa/2014/20141130
  40. ↑ "812.121.11" (PDF). Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Regulation of the EDI about the directories of drugs, psychotropic substances, precursors and auxiliary chemicals) (in German). Das Eidgenössische Departement des Innern (EDI). December 2011.
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