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Indanylaminopropane

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Indanylaminopropane
Systematic (IUPAC) name
(±)-1-(2,3-dihydro-1H-inden-5-yl)propan-2-amine
Clinical data
Pregnancy cat.  ?
Legal status Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Routes Oral
Identifiers
CAS number 152624-02-7
ATC code None
PubChem CID 192600
ChemSpider 167142 YesY
ChEMBL CHEMBL6842 YesY
Synonyms 1-(5-indanyl)-2-aminopropane
Chemical data
Formula C12H17N 
Mol. mass 175.27 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Indanylaminopropane (IAP), sometimes incorrectly referred to as indanylamphetamine,[1] is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes.[2][3] It has been sold by online vendors through the internet and has been encountered as a designer drug since 2003,[1][4][5] but its popularity has diminished in recent years.

IAP acts as a potent and weakly selective serotonin releasing agent (SSRA) with IC50 values of 82 nM, 1,848 nM, and 849 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively.[2][3] It fully substitutes for MBDB but not amphetamine in trained animals, though it does produce disruption for the latter at high doses.[2]

Anecdotal reports suggest that IAP is considerably less stimulating and euphoric than related compounds like MDMA.[4][5] However, in combination with amphetamine, it is said to be virtually indistinguishable from MDA by recreational users.[4][5]

See also

References

  1. ^ a b Casale JF, McKibben TD, Bozenko JS, Hays PA (2005). "Characterization of the "Indanylamphetamines"". Microgram Journal 3 (1-2): 3–10. http://www.usdoj.gov/dea/programs/forensicsci/microgram/journal_v3/mj05_v3_pg1.html. 
  2. ^ a b c Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE (November 1993). "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine". Journal of Medicinal Chemistry 36 (23): 3700–6. doi:10.1021/jm00075a027. PMID 8246240. 
  3. ^ a b Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE (March 1998). "Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry 41 (6): 1001–5. doi:10.1021/jm9705925. PMID 9526575. 
  4. ^ a b c "Bluelight Forums - The Big and Dandy Indanylaminopropane (IAP) Thread". http://www.bluelight.ru/vb/showthread.php?t=97013. 
  5. ^ a b c "Erowid Experience Vaults - Indanylaminopropane (IAP)". http://www.erowid.org/experiences/subs/exp_IAP.shtml. 

External links


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