tametraline

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 448234115

| IUPAC_name = (1R,4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine

| image = Tametraline.svg

| image_class = skin-invert-image

| width = 175

| tradename =

| pregnancy_AU =

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| bioavailability =

| protein_bound =

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| index2_label = HCl

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 52795-02-5

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 52760-47-1

| ATC_prefix = none

| ATC_suffix =

| PubChem = 104180

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| UNII_Ref = {{fdacite|correct|FDA}} (HCl)

| synonyms = CP-24,441

| UNII = 440C8K5Y5K

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 2FY1A2A305

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 143316

| C = 17

| H = 19

| N = 1

| smiles = CN[C@H](CC1)C(C=CC=C2)=C2[C@H]1C3=CC=CC=C3

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C17H19N/c1-18-17-12-11-14(13-7-3-2-4-8-13)15-9-5-6-10-16(15)17/h2-10,14,17-18H,11-12H2,1H3/t14-,17+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = NVXPZMLRGBVYQV-WMLDXEAASA-N

}}

Tametraline (CP-24,441) is the parent of a series of chemical compounds investigated at Pfizer that eventually led to the development of sertraline.{{cite journal | vauthors = Koe BK, Weissman A, Welch WM, Browne RG | title = Sertraline, 1S,4S-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthylamine, a new uptake inhibitor with selectivity for serotonin | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 226 | issue = 3 | pages = 686–700 | date = September 1983 | doi = 10.1016/S0022-3565(25)21773-6 | pmid = 6310078 }}

Sertraline has been called "3,4-dichloro-tametraline". This is correct but it is an oversimplification in the sense that sertraline is the S,S-isomer whereas tametraline is the 1R,4S-stereoisomer.{{Citation needed|date=March 2025}}

1R-Methylamino-4S-phenyl-tetralin is a potent inhibitor of norepinephrine uptake in rat brain synaptosomes,{{cite journal | vauthors = Koe BK | title = Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 199 | issue = 3 | pages = 649–61 | date = December 1976 | doi = 10.1016/S0022-3565(25)30726-3 | pmid = 994022 }} reverses reserpine induced hypothermia in mice, and blocks uptake of ³H-Norepinephrine into rat heart.{{cite journal | vauthors = Sarges R, Koe BK, Weissman A, Schaefer JP | title = Blockade of heart 3H-norepinephrine up-take by 4-phenyl-1-aminotetralines: implications for the active conformation of imipramine-like drugs | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 191 | issue = 3 | pages = 393–402 | date = December 1974 | doi = 10.1016/S0022-3565(25)30003-0 | pmid = 4427286 }}

Tametraline is a norepinephrine–dopamine reuptake inhibitor.{{cite journal | vauthors = Welch WM, Kraska AR, Sarges R, Koe BK | title = Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins | journal = Journal of Medicinal Chemistry | volume = 27 | issue = 11 | pages = 1508–15 | date = November 1984 | pmid = 6492080 | doi = 10.1021/jm00377a021 }}

Indatraline is an indanamine homolog of tetralin-based tametraline, although in the case of indatraline the product is pm-dichlorinated.{{Citation needed|date=March 2025}}