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2-Aminoindane

Chemical compound


Chemical compound

FieldValue
Verifiedfieldschanged
Watchedfieldschanged
verifiedrevid477212458
image2-Aminoindane.svg
image_classskin-invert-image
altStructural formula of 2-aminoindane
width200px
image22-Aminoindane 3D ball.png
image_class2bg-transparent
alt2Ball-and-stick model of the 2-aminoindane molecule
routes_of_administrationOral
classNorepinephrine–dopamine releasing agent; Stimulant
ATC_prefixNone
legal_DENpSG
legal_UKPSA
legal_statusUncontrolled
CAS_number_Ref
CAS_number2975-41-9
PubChem76310
ChemSpiderID_Ref
ChemSpiderID68787
UNII1P810SQ3EY
synonyms2-Indanylamine; 2-Indanamine, SU-8629.
IUPAC_name2,3-Dihydro-1*H*-inden-2-amine
C9H=11N=1
SMILESC1C(CC2=CC=CC=C21)N
StdInChI_Ref
StdInChI1S/C9H11N/c10-9-5-7-3-1-2-4-8(7)6-9/h1-4,9H,5-6,10H2
StdInChIKey_Ref
StdInChIKeyLMHHFZAXSANGGM-UHFFFAOYSA-N

| elimination_half-life =

2-Aminoindane (2-AI) is a stimulant of the 2-aminoindane family which has been sold as a designer drug.

Pharmacology

Pharmacodynamics

2-AI is a monoamine releasing agent acting as a selective substrate for NET and DAT. It partially substitutes for amphetamine in rodent drug discrimination tests.

CompoundMonoamine release (, nM)rowspan="2"RefSerotoninNorepinephrineDopamine
[2-AI](2-aminoindane)10,00086439
[MDAI](5-6-methylenedioxy-2-aminoindane)1141171,334
[MMAI](5-methoxy-6-methyl-2-aminoindane)313,10110,000
[MEAI](5-methoxy-2-aminoindane)1348612,646
*d*-Amphetamine698–1,7656.6–7.25.8–24.8vauthors = Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CWtitle = Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' productsjournal = Neuropsychopharmacologyvolume = 38issue = 4pages = 552–562date = March 2013pmid = 23072836pmc = 3572453doi = 10.1038/npp.2012.204 }}
MDA160–16247–108106–190
MDMA50–8554–11051–278vauthors = Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JStitle = Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotoninjournal = Synapsevolume = 39issue = 1pages = 32–41date = January 2001pmid = 11071707doi = 10.1002/1098-2396(20010101)39:13.0.CO;2-3s2cid = 15573624 }}
[3-MA](3-methoxyamphetamine)ND58.0103
**Notes:** The smaller the value, the more strongly the compound produces the effect. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. **Refs:**

Chemistry

Analogues

2-AI is a rigid analogue of amphetamine and has similar effects in rodents. Other related homologues and rigid analogues of amphetamine include 2-aminotetralin (2-AT), 2-amino-1,2-dihydronapthalene (2-ADN), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 1-phenylpiperazine (1-PP), , and .

Derivatives

Main article: Substituted 2-aminoindane

A number of derivatives of 2-aminoindane, also known as substituted 2-aminoindanes, are known, including 5-IAI, aprindine, BFAI, BFMAI, DHAI, DOM-AI ETAI, indantadol, MDAI, MEAI (5-MeO-2-AI), MDMAI, MMAI, NM-2-AI, PNU-99,194, Pyr-AI, and TAI, among others.

Society and culture

China

As of October 2015 2-AI is a controlled substance in China.

Finland

Scheduled in the "Government decree on psychoactive substances banned from the consumer market".

Sweden

Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.

United States

2-Aminoindane is not scheduled at the federal level in the United States, but may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

References

References

  1. PHARMACOLOGY OF 2-AMINO-INDANE HYDROCHLORIDE (SU-8629): A POTENT NON-NARCOTIC ANALGESIC. Witkin, L.B. et al. The Journal of Pharmacology and Experimental Therapeutics, Volume 133, Issue 3, 400 - 408
  2. (October 2019). "The metabolic fate of two new psychoactive substances - 2-aminoindane and N-methyl-2-aminoindane - studied in vitro and in vivo to support drug testing". Drug Testing and Analysis.
  3. (March 2019). "2-adrenergic receptors". Psychopharmacology.
  4. (March 2014). "Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives". Biochemical Pharmacology.
  5. (March 2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology.
  6. (July 2008). "Dopamine Transporters: Chemistry, Biology and Pharmacology". Wiley.
  7. (2017). "Neuropharmacology of New Psychoactive Substances (NPS)".
  8. (1999). "Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc".
  9. (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse.
  10. (April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology.
  11. (February 2016). "The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue". Neuropharmacology.
  12. (June 2003). "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". Molecular Pharmacology.
  13. (December 2020). "The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats". Psychopharmacology (Berl).
  14. (March 2019). "2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors". Psychopharmacology (Berl).
  15. (March 1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior.
  16. (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacol Biochem Behav.
  17. (May 1982). "A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene". Journal of Medicinal Chemistry.
  18. (1978). "QuaSAR, Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens". Department of Health, Education, and Welfare, Public Health Service, Alcohol, Drug Abuse, and Mental Health Administration.
  19. (February 1974). "Potential psychotomimetics. 2. Rigid analogs of 2,5-dimethoxy-4-methylphenylisopropylamine (DOM, STP)". J Med Chem.
  20. (27 September 2015). "关于印发《非药用类麻醉药品和精神药品列管办法》的通知". China Food and Drug Administration.
  21. "FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014".
  22. (24 June 2019). "Åtta ämnen föreslås klassas som narkotika eller hälsofarlig vara". Folkhälsomyndigheten.
  23. "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.".
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