6-APT

6-(2-Aminopropyl)tetralin (6-APT), also sometimes called tetralinylaminopropane (TAP), is a drug of the amphetamine class which acts as a selective serotonin releasing agent (SSRA).[1] It has IC50 values of 121 nM, 6,436 nM, and 3,371 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively.[1] Though it possesses an appreciable in vitro profile, in animal drug discrimination studies it was not found to substitute for MMAI or amphetamine and to only partially substitute for MBDB.[1] This parallels Alexander Shulgin's finding that EDMA (the 1,4-benzodioxine analogue of 6-APT) is inactive,[2] and appears to indicate that the pharmacokinetics of both EDMA and 6-APT may not be favorable.[1]

6-APT
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Identifiers
IUPAC name
  • 1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC13H19N
Molar mass189.302 g·mol−1
3D model (JSmol)
SMILES
  • CC(CC1=CC2=C(CCCC2)C=C1)N
InChI
  • InChI=1S/C13H19N/c1-10(14)8-11-6-7-12-4-2-3-5-13(12)9-11/h6-7,9-10H,2-5,8,14H2,1H3 Y
  • Key:UTVKUFYOPJCDPE-UHFFFAOYSA-N Y
  (verify)

See also

References
  1. 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.
  2. Ann Shulgin; Alexander Shulgin (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.
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