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'''2-Aminotetralin''' ('''2-AT'''), also known as '''1,2,3,4-tetrahydronaphthalen-2-amine''' ('''THN'''), is a [[stimulant]] [[drug]] with a [[chemical structure]] consisting of a [[tetralin]] [[functional group|group]] combined with an [[amine]].<ref name="pmid2068194">{{cite journal | doi = 10.1016/0091-3057(91)90017-V | author = Oberlender R, Nichols DE. | title = Structural variation and (+)-amphetamine-like discriminative stimulus properties. | journal = Pharmacol Biochem Behav. | volume = 38 | issue = 3 | pages = 581–586 | year = 1991 | pmid = 2068194 }}</ref><ref name="pmid5116035">{{cite journal | author = Marley E, Stephenson JD | title = Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections | journal = [[British Journal of Pharmacology]] | volume = 42 | issue = 4 | pages = 522–42 |date=August 1971 | pmid = 5116035 | pmc = 1665761 | doi = 10.1111/j.1476-5381.1971.tb07138.x| url = }}</ref>
'''2-Aminotetralin''' ('''2-AT'''), also known as '''1,2,3,4-tetrahydronaphthalen-2-amine''' ('''THN'''), is a [[stimulant]] [[drug]] with a [[chemical structure]] consisting of a [[tetralin]] [[functional group|group]] combined with an [[amine]].<ref name="pmid2068194">{{cite journal | doi = 10.1016/0091-3057(91)90017-V | author = Oberlender R, Nichols DE. | title = Structural variation and (+)-amphetamine-like discriminative stimulus properties. | journal = Pharmacol Biochem Behav | volume = 38 | issue = 3 | pages = 581–586 | year = 1991 | pmid = 2068194 }}</ref><ref name="pmid5116035">{{cite journal | author = Marley E, Stephenson JD | title = Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections | journal = [[British Journal of Pharmacology]] | volume = 42 | issue = 4 | pages = 522–42 |date=August 1971 | pmid = 5116035 | pmc = 1665761 | doi = 10.1111/j.1476-5381.1971.tb07138.x| url = }}</ref>


2-AT is a rigid [[Structural analog|analogue]] of [[phenylisobutylamine]] and fully substitutes for [[dextroamphetamine|d-amphetamine]] in rat discrimination tests, although at one eighth the potency.<ref name="pmid2068194" /> It has been shown to [[reuptake inhibitor|inhibit]] the [[reuptake]] of [[serotonin]] and [[norepinephrine]], and likely induces their [[transporter reversal|release]] as well.<ref name="pmid5091160">{{cite journal | author = Bruinvels J | title = Evidence for inhibition of the reuptake of 5-hydroxytryptamine and noradrenaline by tetrahydronaphthylamine in rat brain | journal = British Journal of Pharmacology | volume = 42 | issue = 2 | pages = 281–6 |date=June 1971 | pmid = 5091160 | pmc = 1667157 | doi = 10.1111/j.1476-5381.1971.tb07109.x| url = }}</ref><ref name="pmid4257629">{{cite journal | author = Bruinvels J, Kemper GC | title = Role of noradrenaline and 5-hydroxytryptamine in tetrahydronaphthylamine-induced temperature changes in the rat | journal = British Journal of Pharmacology | volume = 43 | issue = 1 | pages = 1–9 |date=September 1971 | pmid = 4257629 | pmc = 1665934 | doi = 10.1111/j.1476-5381.1971.tb07151.x| url = }}</ref> It is also likely to act on [[dopamine]] on account of its full substitution of d-amphetamine in [[animal testing on rodents|rodent studies]].<ref name="pmid2068194" />
2-AT is a rigid [[Structural analog|analogue]] of [[phenylisobutylamine]] and fully substitutes for [[dextroamphetamine|d-amphetamine]] in rat discrimination tests, although at one eighth the potency.<ref name="pmid2068194" /> It has been shown to [[reuptake inhibitor|inhibit]] the [[reuptake]] of [[serotonin]] and [[norepinephrine]], and likely induces their [[transporter reversal|release]] as well.<ref name="pmid5091160">{{cite journal | author = Bruinvels J | title = Evidence for inhibition of the reuptake of 5-hydroxytryptamine and noradrenaline by tetrahydronaphthylamine in rat brain | journal = British Journal of Pharmacology | volume = 42 | issue = 2 | pages = 281–6 |date=June 1971 | pmid = 5091160 | pmc = 1667157 | doi = 10.1111/j.1476-5381.1971.tb07109.x| url = }}</ref><ref name="pmid4257629">{{cite journal | author = Bruinvels J, Kemper GC | title = Role of noradrenaline and 5-hydroxytryptamine in tetrahydronaphthylamine-induced temperature changes in the rat | journal = British Journal of Pharmacology | volume = 43 | issue = 1 | pages = 1–9 |date=September 1971 | pmid = 4257629 | pmc = 1665934 | doi = 10.1111/j.1476-5381.1971.tb07151.x| url = }}</ref> It is also likely to act on [[dopamine]] on account of its full substitution of d-amphetamine in [[animal testing on rodents|rodent studies]].<ref name="pmid2068194" />

Revision as of 03:11, 8 December 2017

2-Aminotetralin
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1,2,3,4-tetrahydronaphthalen-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.019.067 Edit this at Wikidata
Chemical and physical data
FormulaC10H13N
Molar mass147.217 g/mol g·mol−1
3D model (JSmol)
  • C1CC2=CC=CC=C2CC1N
  • InChI=1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 checkY
  • Key:LCGFVWKNXLRFIF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

2-Aminotetralin (2-AT), also known as 1,2,3,4-tetrahydronaphthalen-2-amine (THN), is a stimulant drug with a chemical structure consisting of a tetralin group combined with an amine.[1][2]

2-AT is a rigid analogue of phenylisobutylamine and fully substitutes for d-amphetamine in rat discrimination tests, although at one eighth the potency.[1] It has been shown to inhibit the reuptake of serotonin and norepinephrine, and likely induces their release as well.[3][4] It is also likely to act on dopamine on account of its full substitution of d-amphetamine in rodent studies.[1]

Chemical derivatives

A number of derivatives of 2-aminotetralin exist, including:

See also

References

  1. ^ a b c Oberlender R, Nichols DE. (1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacol Biochem Behav. 38 (3): 581–586. doi:10.1016/0091-3057(91)90017-V. PMID 2068194.
  2. ^ Marley E, Stephenson JD (August 1971). "Actions of dexamphetamine and amphetamine-like amines in chickens with brain transections". British Journal of Pharmacology. 42 (4): 522–42. doi:10.1111/j.1476-5381.1971.tb07138.x. PMC 1665761. PMID 5116035.
  3. ^ Bruinvels J (June 1971). "Evidence for inhibition of the reuptake of 5-hydroxytryptamine and noradrenaline by tetrahydronaphthylamine in rat brain". British Journal of Pharmacology. 42 (2): 281–6. doi:10.1111/j.1476-5381.1971.tb07109.x. PMC 1667157. PMID 5091160.
  4. ^ Bruinvels J, Kemper GC (September 1971). "Role of noradrenaline and 5-hydroxytryptamine in tetrahydronaphthylamine-induced temperature changes in the rat". British Journal of Pharmacology. 43 (1): 1–9. doi:10.1111/j.1476-5381.1971.tb07151.x. PMC 1665934. PMID 4257629.
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