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2-Aminoindane: Difference between revisions

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{{SubstanceBox/2AI}}
{{SummarySheet}}
'''2-Aminoindane''' ('''2-AI''') is a [[psychoactive drug]] and research chemical with [[stimulant]] properties. It is an analogue of [[amphetamine]].<ref>Structural variation and (+)-amphetamine-like discriminative stimulus properties | https://www.ncbi.nlm.nih.gov/pubmed/2068194</ref>
{{SubstanceBox/2-Aminoindane}}


Very little is known about this substance, but it has recently become freely available through online research chemical vendors where it is being sold as a designer drug.
'''2-Aminoindane''' ('''2-AI''') is a [[psychoactive drug]] and [[research chemical]] with [[psychoactive class::stimulant]] properties. It is an analogue of [[amphetamine]].<ref>{{cite journal | vauthors=((Oberlender, R.)), ((Nichols, D. E.)) | journal=Pharmacology, Biochemistry, and Behavior | title=Structural variation and (+)-amphetamine-like discriminative stimulus properties | volume=38 | issue=3 | pages=581–586 | date= March 1991 | issn=0091-3057 | doi=10.1016/0091-3057(91)90017-v}}</ref>
 
Very little is known about this substance, but it has recently become easily accessible  through online [[research chemical]] vendors where it is being sold as a [[designer drug]].
==Chemistry==
==Chemistry==
2-AI, or 2-Aminoindane, is a structural analogue of [[amphetamine]]. It features the R<sub>3</sub> terminal carbon of the propane chain of amphetamine bound to the benzene ring. This creates an indane group, a bicyclic moeity containing a benzene ring fused to a pentane ring. 2-AI contains an amino group NH<sub>2</sub> bound to R<sub>2</sub> of the indane ring thus giving it the name 2-aminoindane. 2-AI is structurally analogous to NM2AI, lacking the N-substituted methyl group.
2-AI, or 2-[[chemical class::Aminoindane]], is a structural analogue of [[amphetamine]]. It features the R<sub>3</sub> terminal carbon of the propane chain of amphetamine bound to the benzene ring. This creates an indane group, a bicyclic moeity containing a benzene ring fused to a pentane ring. 2-AI contains an amino group NH<sub>2</sub> bound to R<sub>2</sub> of the indane ring thus giving it the name 2-aminoindane. 2-AI is structurally analogous to NM-2-AI, lacking the N-substituted methyl group.


==Pharmacology==
==Pharmacology==
Due to the lack of research regarding the substance, all discussion regarding the pharmacology of it is purely based upon its structure and subjective effect similarities to other [[stimulant]]s such as [[amphetamine]], [[methamphetamine]] and [[2-FMA]]. 2-AI most likely acts as both a [[dopamine]] and [[norepinephrine]] [[reuptake inhibitor]]. This means it effectively boosts the levels of the norepinephrine and dopamine neurotransmitters in the brain by binding to and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft. This allows dopamine and norepinephrine to accumulate within the brain, resulting in [[stimulation|stimulating]] and [[physical euphoria|euphoric]] effects.
Due to the lack of research regarding the substance, all discussion regarding the pharmacology of it is purely based upon its structure and subjective effect similarities to other [[stimulant]]s such as [[amphetamine]], [[methamphetamine]] and [[2-FMA]]. 2-AI most likely acts as both a [[dopamine]] and [[norepinephrine]] [[releasing agent]]. This means it effectively boosts the levels of the norepinephrine and dopamine neurotransmitters in the brain by binding to and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft. This allows dopamine and norepinephrine to accumulate within the brain, resulting in [[stimulation|stimulating]] and [[physical euphoria|euphoric]] effects.


==Subjective effects==
==Subjective effects==
The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|contributors]]. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.                                                                              
{{Preamble/SubjectiveEffects}}                                                                              
===Physical effects===
{{effects/base
The physical effects of 2-AI can be broken down into several components which progressively intensify proportional to dosage. These are described below and generally include:
|{{effects/physical|
 
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the user, 2-AI is usually considered to be energetic and stimulating in a fashion that is similar to that of [[amphetamine]] but stronger than that of [[modafinil]] or [[caffeine]]. It is similar yet distinct from the stimulation experienced on [[MDMA]], encouraging physical activities such as dancing, socializing, running, or cleaning. The particular style of stimulation which 2-AI presents can be described as forced. This means that at higher doses, it becomes difficult or impossible to keep still as jaw clenching, involuntarily bodily shakes and vibrations become present, resulting in extreme shaking of the entire body, unsteadiness of the hands, and a general lack of motor control.  
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the user, 2-AI is usually considered to be energetic and stimulating in a fashion that is similar to that of [[amphetamine]] but stronger than that of [[modafinil]] or [[caffeine]]. It is similar yet distinct from the stimulation experienced on [[MDMA]], encouraging physical activities such as dancing, socializing, running, or cleaning. The particular style of stimulation which 2-AI presents can be described as forced. This means that at higher doses, it becomes difficult or impossible to keep still as jaw clenching, involuntarily bodily shakes and vibrations become present, resulting in extreme shaking of the entire body, unsteadiness of the hands, and a general lack of motor control.  
*'''[[Effect::Pain relief]]''' - Many anecdotal reports suggest that this compound may suppress pain in a fashion somewhat similar to [[opioids]] without the distinct [[physical euphoria]].
*'''[[Effect::Pain relief]]''' - Many anecdotal reports suggest that this compound may suppress pain in a fashion somewhat similar to [[opioids]] without the distinct [[physical euphoria]].
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*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]].
}}


===Cognitive effects===
{{effects/visual|
*'''[[Effect::Acuity enhancement]]'''
}}
|{{effects/cognitive|
The cognitive effects of 2-AI can be broken down into several components which progressively intensify proportional to dosage. The general head space of 2-AI is described by many as one of mental stimulation, increased focus, and euphoria. It contains a large number of typical [[stimulant]] cognitive effects. Although negative side effects are usually mild at low to moderate doses, they become increasingly likely to manifest themselves with higher amounts or extended usage. This particularly holds true during the [[offset]] of the experience.  
The cognitive effects of 2-AI can be broken down into several components which progressively intensify proportional to dosage. The general head space of 2-AI is described by many as one of mental stimulation, increased focus, and euphoria. It contains a large number of typical [[stimulant]] cognitive effects. Although negative side effects are usually mild at low to moderate doses, they become increasingly likely to manifest themselves with higher amounts or extended usage. This particularly holds true during the [[offset]] of the experience.  


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*'''[[Effect::Cognitive euphoria|Euphoria]]'''
*'''[[Effect::Cognitive euphoria|Euphoria]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Cognitive fatigue]]'''  
*'''[[Effect::Increased music appreciation]]'''
 
}}
 
{{effects/aftereffects|
The effects which occur during the [[offset]] of a [[stimulant]] experience generally feel negative and uncomfortable in comparison to the effects which occurred during its [[peak]]. This is often referred to as a "comedown" and occurs because of [[neurotransmitter]] depletion. Its effects commonly include:
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Cognitive fatigue]]'''
*'''[[Effect::Depression]]'''
*'''[[Effect::Depression]]'''
*'''[[Effect::Irritability]]'''
*'''[[Effect::Motivation suppression]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Wakefulness]]'''
}}
}}
===Experience reports===
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:


===Visual effects===
*[https://www.erowid.org/experiences/subs/exp_2Aminoindan.shtml Erowid Experience Vaults: 2-Aminoindane]
*'''[[Effect::Acuity enhancement]]'''


==Toxicity and harm potential==
==Toxicity and harm potential==
The toxicity and long-term health effects of recreational 2-AI use have not been studied in any scientific context and the exact toxic dosage is unknown. This is because 2-AI is a research chemical with very little history of human usage. Anecdotal evidence from people within the [[psychonaut]] community  who have tried 2-AI suggests that there are no negative health effects attributed to simply trying this drug at low to moderate doses or using it very sparingly (but nothing can be completely guaranteed).
{{toxicity}}
{{Further|Research chemicals#Toxicity and harm potential}}
The toxicity and long-term health effects of recreational 2-AI use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]]. This is because 2-AI has very little history of human usage. Anecdotal evidence from people who have tried 2-AI within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed).  


It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
===Tolerance and addiction potential===
===Tolerance and addiction potential===
Tolerance develops rapidly with repeated usage, so periods of extended use require increasing doses of the drug in order to achieve the same effect. Addiction is a serious risk with heavy recreational use of any [[substituted amphetamine]] and compulsive redosing is extremely common.
As with other [[stimulant]]s, the chronic use of 2-AI can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[withdrawal effects]] may occur if a person suddenly stops their usage.


Tolerance to many of the effects of 2-AI [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). 2-AI presents cross-tolerance with [[Cross-tolerance::all [[dopamine]]rgic [[stimulant]]s]], meaning that after the consumption of 2-AI all [[stimulant]]s will have a reduced effect.
===Psychosis===
===Psychosis===
Abuse of compounds within the amphetamine chemical class at high dosages for prolonged periods of time can result in a stimulant psychosis that may present with a variety of symptoms (e.g., [[Paranoia|paranoia]], [[External hallucinations|hallucinations]], or [[Delusions|delusions]]).<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref> A Cochrane Collaboration review on treatment for amphetamine, [[dextroamphetamine]], and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref><ref>Hofmann FG (1983). A Handbook on Drug and Alcohol Abuse: The Biomedical Aspects (2nd ed.). New York: Oxford University Press. p. 329. ISBN 9780195030570.</ref> The same review asserts that, based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis.<ref>Treatment for amphetamine psychosis | [http://onlinelibrary.wiley.com/doi/10.1002/14651858.CD003026.pub3/abstract?systemMessage=Wiley+Online+Library+will+be+disrupted+Saturday%2C+15+March+from+10%3A00-12%3A00+GMT+%2806%3A00-08%3A00+EDT%29+for+essential+maintenance]</ref> Psychosis very rarely arises from therapeutic use.<ref>Stimulant Misuse: Strategies to Manage a Growing Problem | http://www.acha.org/prof_dev/ADHD_docs/ADHD_PDprogram_Article2.pdf</ref><ref>http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf</ref>
{{Main|Stimulant psychosis}}
Abuse of compounds within the stimulant class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., [[Paranoia|paranoia]], [[External hallucinations|hallucinations]], or [[Delusions|delusions]]).<ref name="Shoptaw2009">{{cite journal | vauthors=((Shoptaw, S. J.)), ((Kao, U.)), ((Ling, W.)) | veditors=((Cochrane Drugs and Alcohol Group)) | journal=Cochrane Database of Systematic Reviews | title=Treatment for amphetamine psychosis | date=21 January 2009 | url=https://doi.wiley.com/10.1002/14651858.CD003026.pub3 | issn=14651858 | doi=10.1002/14651858.CD003026.pub3}}</ref> A review on treatment for amphetamine, [[dextroamphetamine]], and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref name="Shoptaw2009"/><ref>{{cite book | vauthors=((Hofmann, F. G.)) | date= 1983 | title=A handbook on drug and alcohol abuse: the biomedical aspects | publisher=Oxford University Press | edition=2nd ed | isbn=9780195030563}}</ref> The same review asserts that, based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis.<ref name="Shoptaw2009"/>


===Dangerous interactions===
===Dangerous interactions===
Although many drugs are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
{{DangerousInteractions/Intro}}
====='''General risk'''=====
 
*'''[[25x-NBOMe]]''' - Both the NBOMe series and amphetamine class induce powerful [[stimulation]]. Side effects such as [[thought loops]], [[seizures]], [[increased blood pressure]], [[vasoconstriction]], [[increased heart rate]], and heart failure (in extreme cases) may occur.
*'''[[DangerousInteraction::Stimulants]]''' - 2-AI can be potentially dangerous in combination with other [[stimulant]]s as it can [[increased heart rate|increase one's heart rate]] and [[increased blood pressure|blood pressure]] to dangerous levels.
*'''[[2C-T-2]]''' - This combination may increase the amount of neurotransmitters (such as dopamine) to dangerous or even fatal levels.
{{DangerousInteractions/Stimulants}}
*'''[[2C-T-7]]''' - This combination may increase the amount of neurotransmitters (such as dopamine) to dangerous or even fatal levels.
*'''[[DangerousInteraction::MDMA]]''' - The neurotoxic effects of MDMA may be increased when combined with [[amphetamine]] and other stimulants.
*'''[[Alcohol]]''' - It is dangerous to combine alcohol, a [[depressant]], with [[stimulants]] due to the risk of excessive intoxication. Stimulants decrease the [[sedation|sedative]] effect of alcohol, which is the main factor most people consider when determining their level of intoxication. Once the stimulant wears off, the effects of alcohol will be significantly increased, leading to intensified [[disinhibition]] as well as [[Alcohol#Subjective effects|other effects]]. If combined, one should strictly limit themselves to only drinking a certain amount of alcohol per hour.
 
*'''[[αMT]]''' - This combination may increase the amount of neurotransmitters (such as dopamine) to dangerous or even fatal levels.
{{DangerousInteractions/MAOI|nt=dopamine}}
*'''[[Cocaine]]''' - This combination will increase strain on the heart.
*'''[[DangerousInteraction::Cocaine]]''' - This combination may increase strain on the heart.
*'''[[DXM]]''' - This combination may cause [[increased heart rate]] and [[Anxiety#Panic attacks|panic attack]]s (for extreme cases).
 
*'''[[MXE]]''' - [[Increased heart rate]] and [[increased blood pressure|blood pressure]] may occur.
==Legal status==
*'''[[Tramadol]]''' - This combination can increase the risk of [[seizures]].
2-AI is currently believed to be a grey area compound within most parts of the world. This means that it is not known to be specifically illegal within any country, but people may still be charged for its possession under certain circumstances such as under analogue laws and with intent to sell or consume.
*'''[[Cocaine]]''' - Heart problems may occur.
*'''[[MDMA]]''' - The neurotoxic effects of [[MDMA]] may be increased when combined with [[amphetamine]]s.
*'''[[MAOIs]]''' - This combination may increase the amount of neurotransmitters (such as dopamine) to dangerous or even fatal levels. Examples include [[syrian rue]], [[banisteriopsis caapi]], and some [[antidepressants]].<ref>Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity | http://bja.oxfordjournals.org/content/95/4/434</ref>


==Legal issues==
*'''Austria''': 2-AI is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}
2-AI is currently a grey area compound within all parts of the world. This means that it is not known to be specifically illegal within any country, but people may still be charged for its possession under certain circumstances such as under analogue laws and with intent to sell or consume.
*'''China''': 2-AI is a controlled substance.<ref>{{cite web|url=http://www.sfda.gov.cn/WS01/CL0056/130753.html|title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 |publisher=China Food and Drug Administration|access-date=December 28, 2019|archive-url=https://web.archive.org/web/20170210033939/www.sfda.gov.cn/WS01/CL0056/130753.html|archive-date=February 10, 2017|language=zh}}</ref>
*'''Germany''': 2-AI is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 25, 2019|language=de}}</ref> as of November 26, 2016.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl116s2615.pdf%27%5D__1576017393518|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|access-date=December 25, 2019|language=de}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 25, 2019|language=de}}</ref> 
*'''Switzerland''': 2-AI is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''United Kingdom''':  2-AI is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>{{Citation | title=Psychoactive Substances Act 2016 | url=https://www.legislation.gov.uk/ukpga/2016/2/contents/enacted}}</ref>


==See also==
==See also==
*[[Responsible use]]
*[[Stimulants]]
*[[Stimulants]]
*[[Amphetamine]]
*[[Amphetamine]]
*[[Methamphetamine]]
*[[Methamphetamine]]
*[[MDAI]]
*[[MDAI]]
==External links==
==External links==
*[https://en.wikipedia.org/wiki/2-Aminoindane 2-AI (Wikipedia)]
*[https://en.wikipedia.org/wiki/2-Aminoindane 2-AI (Wikipedia)]
*[https://www.erowid.org/chemicals/2_aminoindan/2_aminoindan.shtml A-AI (Erowid)]
*[https://erowid.org/chemicals/2_aminoindan/2_aminoindan.shtml 2-AI (Erowid Vault)]
*[http://drugs.tripsit.me/2-ai 2-AI (TripSit factsheets)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=2357 2-Aminoindane (Isomer Design)]
*[https://www.unodc.org/LSS/SubstanceGroup/Details/8fd64573-c567-4734-a258-76d1d95dca25 Aminoindanes (United Nations Office on Drugs and Crime)]


==References==
==References==
<references />
<references />
[[Category:Psychoactive substances]]
[[Category:Psychoactive substance]]
[[Category:Substance]]
[[Category:Substance]]
[[Category:Stimulant]]
[[Category:Stimulant]]
[[Category:Amphetamine]]
[[Category:Aminoindane]]
[[Category:Research chemical]]
 
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