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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
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| IUPAC_name = 1,2,3,4-tetrahydronaphthalen-2-amine
| IUPAC_name = 1,2,3,4-tetrahydronaphthalen-2-amine
| image = 2-Aminotetralin Structure.svg
| image = 2-Aminotetralin Structure.svg
| width =


<!--Clinical data-->
<!--Clinical data-->
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 2954-50-9
| CAS_number = 2954-50-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = LGX8T83G7X
| ATC_prefix = none
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
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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 | vauthors = Oberlender R, Nichols DE | s2cid = 19069907 | title = Structural variation and (+)-amphetamine-like discriminative stimulus properties | journal = Pharmacology, Biochemistry, and Behavior | volume = 38 | issue = 3 | pages = 581–6 | date = March 1991 | pmid = 2068194 | doi = 10.1016/0091-3057(91)90017-V }}</ref><ref name="pmid5116035">{{cite journal | vauthors = 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 }}</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="OberlenderNichols1991">{{cite journal | vauthors = Oberlender R, Nichols DE | s2cid = 19069907 | title = Structural variation and (+)-amphetamine-like discriminative stimulus properties | journal = Pharmacology, Biochemistry, and Behavior | volume = 38 | issue = 3 | pages = 581–586 | date = March 1991 | pmid = 2068194 | doi = 10.1016/0091-3057(91)90017-V | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=77437efa02b4a0f688e4038b153ddfafde6da614 | quote = In previous studies, 2-AT either did not stimulate spontaneous motor activity in mice (1,8), or it had 10% of the activity of amphetamine (24). Yet, in the present study, it mimicked (+)-amphetamine as a DS in rats, in agreement with the results of Glennon et al. (7). However, 2-AT was one-half as potent as (+)-amphetamine in that study but only one-eighth as potent as (+)-amphetamine in the present experiment. }}</ref><ref name="MarleyStephenson1971">{{cite journal | vauthors = 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 = 522–542 | date = August 1971 | pmid = 5116035 | pmc = 1665761 | doi = 10.1111/j.1476-5381.1971.tb07138.x }}</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 | vauthors = 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 }}</ref><ref name="pmid4257629">{{cite journal | vauthors = 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 }}</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 [[drug discrimination]] tests, although at one-half to one-eighth the [[potency (pharmacology)|potency]].<ref name="OberlenderNichols1991" /><ref name="GlennonYoungHauck1984">{{cite journal | vauthors = Glennon RA, Young R, Hauck AE, McKenney JD | title = Structure-activity studies on amphetamine analogs using drug discrimination methodology | journal = Pharmacol Biochem Behav | volume = 21 | issue = 6 | pages = 895–901 | date = December 1984 | pmid = 6522418 | doi = 10.1016/s0091-3057(84)80071-4 | url = }}</ref> It showed greater potency than a variety of other amphetamine homologues, including [[2-Amino-1,2-dihydronaphthalene|2-amino-1,2-dihydronapthalene]] (2-ADN), [[2-aminoindane]] (2-AI), [[naphthylaminopropane|1-naphthylaminopropane]] (1-NAP), [[2-naphthylaminopropane]] (2-NAP), [[phenylpiperazine|1-phenylpiperazine]] (1-PP), {{Abbrlink|6-AB|6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene}}, and {{Abbrlink|7-AB|7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene}}.<ref name="GlennonYoungHauck1984" /><ref name="OberlenderNichols1991" /><ref name="HathawayNicholsYim1982">{{cite journal |vauthors=Hathaway BA, Nichols DE, Nichols MB, Yim GK | title = A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene | journal = Journal of Medicinal Chemistry | volume = 25 | issue = 5 | pages = 535–538 |date=May 1982 | pmid = 6123601 | doi = 10.1021/jm00347a011}}</ref>

2-AT has been shown to [[reuptake inhibitor|inhibit]] the [[reuptake]] of [[serotonin]] and [[norepinephrine]], and might induce their [[transporter reversal|release]] as well.<ref name="Bruinvels1971">{{cite journal | vauthors = 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 = 281–286 | date = June 1971 | pmid = 5091160 | pmc = 1667157 | doi = 10.1111/j.1476-5381.1971.tb07109.x }}</ref><ref name="BruinvelsKemper1971">{{cite journal | vauthors = 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 }}</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="OberlenderNichols1991" /><ref name="GlennonYoungHauck1984" />


== Chemical derivatives ==
== Chemical derivatives ==

A number of [[chemical derivative|derivative]]s of 2-aminotetralin exist, including:
A number of [[chemical derivative|derivative]]s of 2-aminotetralin exist, including:


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* [[5-OH-DPAT]]
* [[5-OH-DPAT]]
* [[6-Chloro-2-aminotetralin|6-CAT]]
* [[6-Chloro-2-aminotetralin|6-CAT]]
* [[6-OH-DPAT]]
* [[7-OH-DPAT]]
* [[7-OH-DPAT]]
* [[7-OH-PIPAT]]
* [[8-OH-DPAT]]
* [[8-OH-DPAT]]
* [[AS-19 (drug)|AS-19]]
* [[AS-19 (drug)|AS-19]]
* [[N,N-dipropyl-5,6-dihydroxy-2-aminotetralin|DP-5,6-ADTN]]
* [[Lometraline]]
* [[6,7-Methylenedioxy-2-aminotetralin|MDAT]]
* [[6,7-Methylenedioxy-2-aminotetralin|MDAT]]
* [[6,7-Methylenedioxy-N-methyl-2-aminotetralin|MDMAT]]
* [[6,7-Methylenedioxy-N-methyl-2-aminotetralin|MDMAT]]
* [[2-(N-propyl-N-phenylethylamino)-5-hydroxytetralin|N-0434]]
* [[RDS-127]]
* [[Sertraline]]
* [[SR-59,230-A]]
* [[Tametraline]]
* [[UH-232]]
* [[UH-232]]
*5,6-ADTN []
*6,7-ADTN []
}}
}}

== See also ==
* [[2-Aminodilin]]
* [[2-Aminoindane]]


== References ==
== References ==
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{{DEFAULTSORT:Aminotetralin, 2-}}
{{DEFAULTSORT:Aminotetralin, 2-}}
[[Category:Aminotetralins]]
[[Category:2-Aminotetralins|*]]
[[Category:Stimulants]]
[[Category:Stimulants]]
[[Category:Serotonin-norepinephrine-dopamine releasing agents]]
[[Category:Serotonin-norepinephrine-dopamine releasing agents]]

Latest revision as of 06:02, 8 December 2024

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
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.019.067 Edit this at Wikidata
Chemical and physical data
FormulaC10H13N
Molar mass147.221 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 drug discrimination tests, although at one-half to one-eighth the potency.[1][3] It showed greater potency than a variety of other amphetamine homologues, including 2-amino-1,2-dihydronapthalene (2-ADN), 2-aminoindane (2-AI), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 1-phenylpiperazine (1-PP), 6-ABTooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-ABTooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene.[3][1][4]

2-AT has been shown to inhibit the reuptake of serotonin and norepinephrine, and might induce their release as well.[5][6] It is also likely to act on dopamine on account of its full substitution of d-amphetamine in rodent studies.[1][3]

Chemical derivatives

[edit]

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

References

[edit]
  1. ^ a b c d Oberlender R, Nichols DE (March 1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior. 38 (3): 581–586. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. S2CID 19069907. In previous studies, 2-AT either did not stimulate spontaneous motor activity in mice (1,8), or it had 10% of the activity of amphetamine (24). Yet, in the present study, it mimicked (+)-amphetamine as a DS in rats, in agreement with the results of Glennon et al. (7). However, 2-AT was one-half as potent as (+)-amphetamine in that study but only one-eighth as potent as (+)-amphetamine in the present experiment.
  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): 522–542. doi:10.1111/j.1476-5381.1971.tb07138.x. PMC 1665761. PMID 5116035.
  3. ^ a b c Glennon RA, Young R, Hauck AE, McKenney JD (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacol Biochem Behav. 21 (6): 895–901. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418.
  4. ^ Hathaway BA, Nichols DE, Nichols MB, Yim GK (May 1982). "A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene". Journal of Medicinal Chemistry. 25 (5): 535–538. doi:10.1021/jm00347a011. PMID 6123601.
  5. ^ 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): 281–286. doi:10.1111/j.1476-5381.1971.tb07109.x. PMC 1667157. PMID 5091160.
  6. ^ 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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