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6-APT

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
6-APT
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(5,6,7,8-Tetrahydronaphthalen-2-yl)propan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H19N
Molar mass189.302 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(CCCC2)C=C1)N
  • 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 checkY
  • Key:UTVKUFYOPJCDPE-UHFFFAOYSA-N checkY
  (verify)

6-(2-Aminopropyl)tetralin (6-APT), also sometimes calledtetralinylaminopropane (TAP), is adrug of theamphetamine class which acts as aselective serotonin releasing agent (SSRA).[1] It hasIC50 values of 121 nM, 6,436 nM, and 3,371 nM forinhibiting thereuptake ofserotonin,dopamine, andnorepinephrine, respectively.[1] Though it possesses an appreciablein vitro profile, in animaldrug discrimination studies it was not found to substitute forMMAI oramphetamine and to only partially substitute forMBDB.[1] This parallelsAlexander Shulgin's finding thatEDMA (the1,4-benzodioxineanalogue of 6-APT) is limitedlyactive,[2] and appears to indicate that thepharmacokinetics of both EDMA and 6-APT may not be favorable.[1]

See also

[edit]

References

[edit]
  1. ^abcdMonte 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):3700–3706.doi:10.1021/jm00075a027.PMID 8246240.
  2. ^Shulgin A, Shulgin A (13 May 2016)."EDMA · 3,4-Ethylenedioxy-N-methylamphetamine".Pihkal: A Chemical Love Story. Transform Press.ISBN 978-0-9630096-0-9.
Phenylalkyl-
amines

(other than
cathinones)
Cyclizedphenyl-
alkylamines
Cathinones
Tryptamines
Chemical classes
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous
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