| Revision as of 08:47, 14 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit |
Latest revision as of 06:02, 8 December 2024 edit undo76.174.0.57 (talk) Add missing analogue. |
| (59 intermediate revisions by 31 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
|
| verifiedrevid = 399207366 |
|
| verifiedrevid = 477212588 |
|
| IUPAC_name = 1,2,3,4-tetrahydronaphthalen-2-amine |
|
| IUPAC_name = 1,2,3,4-tetrahydronaphthalen-2-amine |
|
| image = 2-Aminotetralin.png |
|
| image = 2-Aminotetralin Structure.svg |
|
|
| width = |
|
|
|
|
|
<!--Clinical data--> |
|
|
| tradename = |
|
⚫ |
| pregnancy_category = |
|
⚫ |
| legal_status = Uncontrolled |
|
⚫ |
| routes_of_administration = Oral |
|
|
|
|
|
<!--Pharmacokinetic data--> |
|
⚫ |
| bioavailability = |
|
⚫ |
| metabolism = |
|
⚫ |
| elimination_half-life = |
|
⚫ |
| excretion = |
|
|
|
|
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|correct|CAS}} |
|
⚫ |
| CAS_number = 2954-50-9 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = LGX8T83G7X |
|
⚫ |
| ATC_prefix = none |
|
⚫ |
| ATC_suffix = |
|
⚫ |
| PubChem = 34677 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 31912 |
|
| ChemSpiderID = 31912 |
|
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| InChI = 1/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 |
|
|
| InChIKey = LCGFVWKNXLRFIF-UHFFFAOYAA |
|
|
| smiles1 = c1ccc2c(c1)CCC(C2)N |
|
|
| ChEMBL = 30294 |
|
| ChEMBL = 30294 |
|
|
|
|
|
<!--Chemical data--> |
|
⚫ |
| C=10 | H=13 | N=1 |
|
⚫ |
| smiles = C1CC2=CC=CC=C2CC1N |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 |
|
| StdInChI = 1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = LCGFVWKNXLRFIF-UHFFFAOYSA-N |
|
| StdInChIKey = LCGFVWKNXLRFIF-UHFFFAOYSA-N |
| ⚫ |
| CAS_number = 2954-50-9 |
|
| ⚫ |
| ATC_prefix = none |
|
| ⚫ |
| ATC_suffix = |
|
| ⚫ |
| PubChem = 34677 |
|
| ⚫ |
| C = 10 | H = 13 | N = 1 |
|
|
| molecular_weight = 147.217 g/mol |
|
| ⚫ |
| smiles = C1CC2=CC=CC=C2CC1N |
|
| ⚫ |
| bioavailability = |
|
| ⚫ |
| metabolism = |
|
| ⚫ |
| elimination_half-life = |
|
| ⚫ |
| excretion = |
|
| ⚫ |
| pregnancy_category = |
|
| ⚫ |
| legal_status = Uncontrolled |
|
| ⚫ |
| routes_of_administration = Oral |
|
|
}} |
|
}} |
|
|
|
|
|
'''2-Aminotetralin''' ('''2-AT'''), also known as '''1,2,3,4-tetrahydronaphthalen-2-amine''' ('''THN'''), is a ] ] with a ] consisting of a ] ] combined with an ].<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 | year = 1971 | month = August | pmid = 5116035 | pmc = 1665761 | doi = | url = }}</ref> |
|
'''2-Aminotetralin''' ('''2-AT'''), also known as '''1,2,3,4-tetrahydronaphthalen-2-amine''' ('''THN'''), is a ] ] with a ] consisting of a ] ] combined with an ].<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 ] of ] and fully substitutes for ] in rat discrimination tests, although at 1/8th the potency.<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> It has been shown to ] the ] of ] and ], and likely induces their ] 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 | year = 1971 | month = June | pmid = 5091160 | pmc = 1667157 | doi = | 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 | year = 1971 | month = September | pmid = 4257629 | pmc = 1665934 | doi = | url = }}</ref> It is also likely to act on ] on account of its full substitution of d-amphetamine in rodent studies.<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> |
|
2-AT is a rigid ] of ] and fully substitutes for ] in rat ] tests, although at one-half to one-eighth the ].<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-ADN), ] (2-AI), ] (1-NAP), ] (2-NAP), ] (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 ] the ] of ] and ], and might induce their ] 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 ] on account of its full substitution of d-amphetamine in ].<ref name="OberlenderNichols1991" /><ref name="GlennonYoungHauck1984" /> |
| ⚫ |
== Chemical derivatives == |
|
|
|
|
|
|
⚫ |
== Chemical derivatives == |
|
A number of ]s of 2-aminotetralin exist, including: |
|
A number of ]s of 2-aminotetralin exist, including: |
|
|
|
|
|
|
{{columns-list|colwidth=15em| |
|
<div style="-moz-column-count:2; column-count:2; -webkit-column-count:2;"> |
|
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
|
* ] |
|
* ] |
|
* ] |
|
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
|
* ] |
|
|
* ] |
|
|
* ] |
|
|
* ] |
|
|
* ] |
|
* ] |
|
|
}} |
|
</div> |
|
|
|
|
|
== See also == |
|
|
* ] |
|
|
* ] |
|
|
* ] |
|
|
|
|
|
|
== References == |
|
== References == |
|
{{Reflist}} |
|
{{Reflist|2}} |
|
|
|
|
|
|
|
|
{{Stimulants}} |
|
{{Stimulants}} |
|
|
{{Monoamine releasing agents}} |
|
{{Adrenergics}} |
|
|
{{Dopaminergics}} |
|
|
{{Serotonergics}} |
|
|
|
|
|
|
{{DEFAULTSORT:Aminotetralin, 2-}} |
|
{{DEFAULTSORT:Aminotetralin, 2-}} |
|
⚫ |
] |
|
|
|
| ⚫ |
] |
|
|
] |
|
|
] |
|
] |
|
|
] |