2-Aminotetralin

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-Aminotetralin

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 1,2,3,4-tetrahydronaphthalen-2-amine
CAS Number	2954-50-9
PubChem CID	34677
ChemSpider	31912
ChEMBL	ChEMBL30294
ECHA InfoCard	100.019.067
Chemical and physical data
Formula	C10H13N
Molar mass	147.221 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C1CC2=CC=CC=C2CC1N
InChI InChI=1S/C10H13N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4,10H,5-7,11H2 Key:LCGFVWKNXLRFIF-UHFFFAOYSA-N
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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:

• 5-OH-DPAT
• 6-CAT
• 6-OH-DPAT
• 7-OH-DPAT
• 7-OH-PIPAT
• 8-OH-DPAT
• AS-19
• DP-5,6-ADTN
• Lometraline
• MDAT
• MDMAT
• N-0434
• RDS-127
• Sertraline
• SR-59,230-A
• Tametraline
• UH-232

See also

• 2-Aminodilin
• 2-Aminoindane

References

1. Oberlender R, Nichols DE (March 1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior. 38 (3): 581–6. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. S2CID 19069907.
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.