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| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 456692449
| verifiedrevid = 456692449
| IUPAC_name = 2-Chloro-11-(piperazin-1-yl)dibenzo[''b,f''][1,4]oxazepine
| IUPAC_name = 2-chloro-11-(piperazin-1-yl)dibenzo[''b,f''][1,4]oxazepine
| image = Amoxapine.svg
| image = Amoxapine.svg
| width = 200px
| width = 200px
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<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| protein_bound = 90%<ref name="pmid6764165">{{cite journal | author = Kinney JL, Evans RL | title = Evaluation of amoxapine | journal = Clinical Pharmacy | volume = 1 | issue = 5 | pages = 417–24 | year = 1982 | pmid = 6764165 | doi = | url = }}</ref>
| bioavailability = ?
| bioavailability = ?
| metabolism = Hepatic ([[cytochrome P450|cytochrome P450 system]])
| metabolism = Hepatic ([[cytochrome P450|cytochrome P450 system]])
| elimination_half-life = 8-10 hours (30 hours for major metabolites)
| elimination_half-life = 8-10 hours (30 hours for major metabolites)<ref name="pmid6764165" />
| excretion = Renal
| excretion = Renal


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<!--Chemical data-->
<!--Chemical data-->
| C=17 | H=16 | Cl=1 | N=3 | O=1
| C = 17 | H = 16 | Cl = 1 | N = 3 | O = 1
| molecular_weight = 313.781
| molecular_weight = 313.781 g/mol
| smiles = Clc2ccc1Oc4c(/N=C(\c1c2)N3CCNCC3)cccc4
| smiles = Clc2ccc1Oc4c(/N=C(\c1c2)N3CCNCC3)cccc4
| InChI = 1/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2
| InChI = 1/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2
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}}
}}


'''Amoxapine''' ('''Amokisan''', '''Asendin''', '''Asendis''', '''Defanyl''', '''Demolox''', '''Moxadil''') is a [[tetracyclic antidepressant]] (TeCA) of the [[dibenzoxazepine]] class, though some authorities classify it as a secondary amine [[tricyclic antidepressant]].
'''Amoxapine''' ('''Amokisan''', '''Asendin''', '''Asendis''', '''Defanyl''', '''Demolox''', '''Moxadil''') is a [[tetracyclic antidepressant]] of the [[dibenzoxazepine]] family, though it is often classified as a [[wiktionary:secondary amine|secondary amine]] [[tricyclic antidepressant]].


== Uses ==
== Uses ==
Amoxapine is used in the treatment of [[clinical depression|depression]], [[anxiety disorder]]s, [[panic disorder]], and [[bipolar disorder]]. It also has properties similar to those of [[atypical antipsychotic]],<ref name="pmid6126130">{{cite journal | author = Cohen BM, Harris PQ, Altesman RI, Cole JO | title = Amoxapine: neuroleptic as well as antidepressant? | journal = The American Journal of Psychiatry | volume = 139 | issue = 9 | pages = 1165–7 | year = 1982 | month = September | pmid = 6126130 | doi = | url = http://ajp.psychiatryonline.org/article.aspx?volume=139&page=1165}}</ref><ref name="pmid15956984">{{cite journal | author = Apiquian R, Fresan A, Ulloa RE, ''et al.'' | title = Amoxapine as an atypical antipsychotic: a comparative study vs risperidone | journal = Neuropsychopharmacology | volume = 30 | issue = 12 | pages = 2236–2244 | year = 2005 | month = December | pmid = 15956984 | doi = 10.1038/sj.npp.1300796}}</ref> and may be used in the treatment of [[schizophrenic]] [[psychosis]] off-label.
Amoxapine is used in the treatment of [[clinical depression|depression]], [[anxiety disorder]]s, [[panic disorder]], and [[bipolar disorder]]. Amoxapine is contra indicated in children because it lowers the seizure threshold to the extent that fits may be precipitated, especially in children. Cardiovascular effects and anti-cholinergic side effects are much reduced.
It also has action similar to an [[atypical antipsychotic]].<ref name="pmid15956984">{{cite journal |author=Apiquian R, Fresan A, Ulloa RE, ''et al.'' |title=Amoxapine as an atypical antipsychotic: a comparative study vs risperidone |journal=Neuropsychopharmacology |volume=30 |issue=12 |pages=2236–44 |year=2005 |month=December |pmid=15956984 |doi=10.1038/sj.npp.1300796}}</ref>


== Pharmacology ==
== Pharmacology ==
Amoxapine possesses a wide array of pharmacological effects. It is a moderate and strong [[reuptake inhibitor]] of [[serotonin]] and [[norepinephrine]], respectively,<ref name="pmid9537821">{{cite journal | author = Tatsumi M, Groshan K, Blakely RD, Richelson E | title = Pharmacological profile of antidepressants and related compounds at human monoamine transporters | journal = European Journal of Pharmacology | volume = 340 | issue = 2-3 | pages = 249–58 | year = 1997 | month = December | pmid = 9537821 | doi = | url = http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(97)01393-9}}</ref> and binds to the [[5-HT2A receptor|5-HT<sub>2A</sub>]],<ref name="pmid8876023">{{cite journal | author = Pälvimäki EP, Roth BL, Majasuo H, ''et al.'' | title = Interactions of selective serotonin reuptake inhibitors with the serotonin 5-HT2c receptor | journal = Psychopharmacology | volume = 126 | issue = 3 | pages = 234–40 | year = 1996 | month = August | pmid = 8876023 | doi = | url = http://link.springer.de/link/service/journals/00213/bibs/6126003/61260234.htm}}</ref> [[5-HT2B receptor|5-HT<sub>2B</sub>]],<ref name="pmid10821800">{{cite journal | author = Glusa E, Pertz HH | title = Further evidence that 5-HT-induced relaxation of pig pulmonary artery is mediated by endothelial 5-HT(2B) receptors | journal = British Journal of Pharmacology | volume = 130 | issue = 3 | pages = 692–8 | year = 2000 | month = June | pmid = 10821800 | pmc = 1572101 | doi = 10.1038/sj.bjp.0703341 | url = http://dx.doi.org/10.1038/sj.bjp.0703341}}</ref> [[5-HT2C receptor|5-HT<sub>2C</sub>]],<ref name="pmid8876023" /> [[5-HT3 receptor|5-HT<sub>3</sub>]],<ref name="pmid1666997">{{cite journal | author = Gozlan H, Saddiki-Traki F, Merahi N, Laguzzi R, Hamon M | title = [Preclinical pharmacology of amoxapine and amitriptyline. Implications of serotoninergic and opiodergic systems in their central effect in rats] | language = French | journal = L'Encéphale | volume = 17 Spec No 3 | issue = | pages = 415–22 | year = 1991 | month = December | pmid = 1666997 | doi = | url = }}</ref> [[5-HT6 receptor|5-HT<sub>6</sub>]],<ref name="pmid7908055">{{cite journal | author = Roth BL, Craigo SC, Choudhary MS, ''et al.'' | title = Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 268 | issue = 3 | pages = 1403–10 | year = 1994 | month = March | pmid = 7908055 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7908055}}</ref> [[5-HT7 receptor|5-HT<sub>7</sub>]],<ref name="pmid7908055" /> [[D2 receptor|D<sub>2</sub>]],<ref name="pmid6086881">{{cite journal | author = Richelson E, Nelson A | title = Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 230 | issue = 1 | pages = 94–102 | year = 1984 | month = July | pmid = 6086881 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=6086881}}</ref> [[alpha-1 adrenergic receptor|α<sub>1</sub>-adrenergic]],<ref name="pmid6086881" /> [[D3 receptor|D<sub>3</sub>]]<ref name="pmid16135699">{{cite journal | author = Burstein ES, Ma J, Wong S, ''et al.'' | title = Intrinsic efficacy of antipsychotics at human D2, D3, and D4 dopamine receptors: identification of the clozapine metabolite N-desmethylclozapine as a D2/D3 partial agonist | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 315 | issue = 3 | pages = 1278–87 | year = 2005 | month = December | pmid = 16135699 | doi = 10.1124/jpet.105.092155 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=16135699}}</ref>, [[D4 receptor|D<sub>4</sub>]],<ref name="pmid16135699" /> and [[H1 receptor|H<sub>1</sub> receptor]]s<ref name="pmid6086881" /> with varying but significant [[affinity (pharmacology)|affinity]], where it acts as an [[receptor antagonist|antagonist]] (or [[inverse agonist]] depending on the receptor in question) at all sites. It has weak but negligible affinity for the [[dopamine transporter]] and the [[5-HT1A receptor|5-HT<sub>1A</sub>]],<ref name="pmid1666997">{{cite journal | author = Gozlan H, Saddiki-Traki F, Merahi N, Laguzzi R, Hamon M | title = [Preclinical pharmacology of amoxapine and amitriptyline. Implications of serotoninergic and opiodergic systems in their central effect in rats] | language = French | journal = L'Encéphale | volume = 17 Spec No 3 | issue = | pages = 415–22 | year = 1991 | month = December | pmid = 1666997 | doi = | url = }}</ref> [[5-HT1B receptor|5-HT<sub>1B</sub>]],<ref name="pmid1666997" /> [[D1 receptor|D<sub>1</sub>]],<ref name="pmid1966571">{{cite journal | author = Wei HB, Niu XY | title = [Comparison of the affinities of amoxapine and loxapine for various receptors in rat brain and the receptor down-regulation after chronic administration] | language = Chinese | journal = Yao Xue Xue Bao = Acta Pharmaceutica Sinica | volume = 25 | issue = 12 | pages = 881–5 | year = 1990 | pmid = 1966571 | doi = | url = }}</ref> [[alpha-2 adrenergic receptor|α<sub>2</sub>-adrenergic]],<ref name="pmid6086881" /> [[H4 receptor|H<sub>4</sub>]],<ref name="pmid15947036">{{cite journal | author = Lim HD, van Rijn RM, Ling P, Bakker RA, Thurmond RL, Leurs R | title = Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 314 | issue = 3 | pages = 1310–21 | year = 2005 | month = September | pmid = 15947036 | doi = 10.1124/jpet.105.087965 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15947036}}</ref> [[muscarinic acetylcholine receptor|mACh]],<ref name="pmid6086881" /> and [[GABAA receptor|GABA<sub>A</sub> receptors]],<ref name="pmid1966571" /> and no affinity for the [[beta-adrenergic receptor|β-adrenergic receptor]]s or the [[allosteric regulation|allosteric]] [[benzodiazepine site]] on the GABA<sub>A</sub> receptor.<ref name="pmid1966571" />
Amoxapine is a strong [[norepinephrine reuptake inhibitor]] and weak [[serotonin reuptake inhibitor]]. It also possesses [[antiadrenergic]], [[anticholinergic]], [[antidopaminergic]], [[antihistamine]], and [[antiserotonergic]] properties.


[[7-Hydroxyamoxapine]], a major [[active metabolite]] of amoxapine, is a more [[potency (pharmacology)|potent]] [[dopamine receptor]] antagonist and contributes to its neuroleptic efficacy,<ref name="pmid6126130">{{cite journal | author = Cohen BM, Harris PQ, Altesman RI, Cole JO | title = Amoxapine: neuroleptic as well as antidepressant? | journal = The American Journal of Psychiatry | volume = 139 | issue = 9 | pages = 1165–7 | year = 1982 | month = September | pmid = 6126130 | doi = | url = http://ajp.psychiatryonline.org/article.aspx?volume=139&page=1165}}</ref> whereas [[8-hydroxyamoxapine]] is a [[norepinephrine reuptake inhibitor]] but a stronger [[serotonin reuptake inhibitor]] and helps to balance amoxapine's ratio of [[serotonin transporter|serotonin]] to [[norepinephrine transporter]] blockade.<ref name="pmid10507241">{{cite journal | author = Midha KK, Hubbard JW, McKay G, Rawson MJ, Hsia D | title = The role of metabolites in a bioequivalence study II: amoxapine, 7-hydroxyamoxapine, and 8-hydroxyamoxapine | journal = International Journal of Clinical Pharmacology and Therapeutics | volume = 37 | issue = 9 | pages = 428–38 | year = 1999 | month = September | pmid = 10507241 | doi = | url = }}</ref>
== Side effects ==
One of its major metabolites, [[7-hydroxyamoxapine]], has a [[dopamine]] receptor blocking effect, making this drug a common cause of [[neuroleptic malignant syndrome]]. Amoxapine is also associated with acute [[extrapyramidal symptoms]] and [[tardive dyskinesia]].


== Special precautions ==
== Side effects ==
Common [[side effect]]s of amoxapine include [[hypotension]], [[drowsiness]], [[dry mouth]], [[constipation]], [[blurred vision]], [[fatigue]], and [[vertigo]].<ref name="pmid6764165" /> Additionally, due to the drug's and its metabolite 7-hyroxyamoxapine's potent blockade of dopamine receptors, it can cause [[neuroleptic malignant syndrome]] as well as acute [[extrapyramidal symptoms]] and [[tardive dyskinesia]]. Cardiovascular and [[anticholinergic]] side effects are much reduced compared to other tri- and tetracyclic antidepressants.
Mania, hypomania, severe liver damage, diabetes, myocardial infarction, epilepsy.{{Clarify|date=December 2010}}


== Drug Interactions ==
== Contraindications ==
The drug is contraindicated in children because it lowers the seizure threshold to the extent that fits may be precipitated.{{Citation needed|date=November 2011}}
potential sedative effects of alcohol, antiparkinson, agents, reduce effects of sympathomimetics.


== See also ==
== See also ==
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{{Reflist|2}}
{{Reflist|2}}


== Further reading==
* Mosby Year-Book, Inc. (1995). ''Physician's GenRx: The Complete Drug Reference (5th Ed.)''. Riverside, CT: Denniston Publishing Co.
* Palfai, T. & Jankiewicz, H. (1997). ''Drugs and Human Behavior (2nd Ed.)''. Madison, WI: Brown & Benchmark.
* Hedges, D. & Burchfield, C. (2006). ''Mind, Brain, and Drug: An Introduction to Psychopharmacology.'' Boston, MA: Pearson.


{{Antidepressants}}
{{Antidepressants}}
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{{Antipsychotics}}
{{Antipsychotics}}
{{Adrenergics}}
{{Adrenergics}}
{{Cholinergics}}
{{Dopaminergics}}
{{Dopaminergics}}
{{Histaminergics}}
{{Histaminergics}}
Line 95: Line 89:


[[Category:Norepinephrine reuptake inhibitors]]
[[Category:Norepinephrine reuptake inhibitors]]
[[Category:Serotonin reuptake inhibitors]]
[[Category:Piperazines]]
[[Category:Piperazines]]
[[Category:Treatment of bipolar disorder]]
[[Category:Treatment of bipolar disorder]]

Revision as of 00:59, 28 November 2011

Amoxapine
Clinical data
Trade namesAsendin
AHFS/Drugs.comMonograph
MedlinePlusa682202
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability?
Protein binding90%[2]
MetabolismHepatic (cytochrome P450 system)
Elimination half-life8-10 hours (30 hours for major metabolites)[2]
ExcretionRenal
Identifiers
  • 2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.034.411 Edit this at Wikidata
Chemical and physical data
FormulaC17H16ClN3O
Molar mass313.781 g/mol g·mol−1
3D model (JSmol)
  • Clc2ccc1Oc4c(/N=C(\c1c2)N3CCNCC3)cccc4
  • InChI=1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2 checkY
  • Key:QWGDMFLQWFTERH-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Amoxapine (Amokisan, Asendin, Asendis, Defanyl, Demolox, Moxadil) is a tetracyclic antidepressant of the dibenzoxazepine family, though it is often classified as a secondary amine tricyclic antidepressant.

Uses

Amoxapine is used in the treatment of depression, anxiety disorders, panic disorder, and bipolar disorder. It also has properties similar to those of atypical antipsychotic,[3][4] and may be used in the treatment of schizophrenic psychosis off-label.

Pharmacology

Amoxapine possesses a wide array of pharmacological effects. It is a moderate and strong reuptake inhibitor of serotonin and norepinephrine, respectively,[5] and binds to the 5-HT2A,[6] 5-HT2B,[7] 5-HT2C,[6] 5-HT3,[8] 5-HT6,[9] 5-HT7,[9] D2,[10] α1-adrenergic,[10] D3[11], D4,[11] and H1 receptors[10] with varying but significant affinity, where it acts as an antagonist (or inverse agonist depending on the receptor in question) at all sites. It has weak but negligible affinity for the dopamine transporter and the 5-HT1A,[8] 5-HT1B,[8] D1,[12] α2-adrenergic,[10] H4,[13] mACh,[10] and GABAA receptors,[12] and no affinity for the β-adrenergic receptors or the allosteric benzodiazepine site on the GABAA receptor.[12]

7-Hydroxyamoxapine, a major active metabolite of amoxapine, is a more potent dopamine receptor antagonist and contributes to its neuroleptic efficacy,[3] whereas 8-hydroxyamoxapine is a norepinephrine reuptake inhibitor but a stronger serotonin reuptake inhibitor and helps to balance amoxapine's ratio of serotonin to norepinephrine transporter blockade.[14]

Side effects

Common side effects of amoxapine include hypotension, drowsiness, dry mouth, constipation, blurred vision, fatigue, and vertigo.[2] Additionally, due to the drug's and its metabolite 7-hyroxyamoxapine's potent blockade of dopamine receptors, it can cause neuroleptic malignant syndrome as well as acute extrapyramidal symptoms and tardive dyskinesia. Cardiovascular and anticholinergic side effects are much reduced compared to other tri- and tetracyclic antidepressants.

Contraindications

The drug is contraindicated in children because it lowers the seizure threshold to the extent that fits may be precipitated.[citation needed]

See also

References

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ a b c Kinney JL, Evans RL (1982). "Evaluation of amoxapine". Clinical Pharmacy. 1 (5): 417–24. PMID 6764165.
  3. ^ a b Cohen BM, Harris PQ, Altesman RI, Cole JO (1982). "Amoxapine: neuroleptic as well as antidepressant?". The American Journal of Psychiatry. 139 (9): 1165–7. PMID 6126130. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Apiquian R, Fresan A, Ulloa RE; et al. (2005). "Amoxapine as an atypical antipsychotic: a comparative study vs risperidone". Neuropsychopharmacology. 30 (12): 2236–2244. doi:10.1038/sj.npp.1300796. PMID 15956984. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. ^ Tatsumi M, Groshan K, Blakely RD, Richelson E (1997). "Pharmacological profile of antidepressants and related compounds at human monoamine transporters". European Journal of Pharmacology. 340 (2–3): 249–58. PMID 9537821. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  6. ^ a b Pälvimäki EP, Roth BL, Majasuo H; et al. (1996). "Interactions of selective serotonin reuptake inhibitors with the serotonin 5-HT2c receptor". Psychopharmacology. 126 (3): 234–40. PMID 8876023. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  7. ^ Glusa E, Pertz HH (2000). "Further evidence that 5-HT-induced relaxation of pig pulmonary artery is mediated by endothelial 5-HT(2B) receptors". British Journal of Pharmacology. 130 (3): 692–8. doi:10.1038/sj.bjp.0703341. PMC 1572101. PMID 10821800. {{cite journal}}: Unknown parameter |month= ignored (help)
  8. ^ a b c Gozlan H, Saddiki-Traki F, Merahi N, Laguzzi R, Hamon M (1991). "[Preclinical pharmacology of amoxapine and amitriptyline. Implications of serotoninergic and opiodergic systems in their central effect in rats]". L'Encéphale (in French). 17 Spec No 3: 415–22. PMID 1666997. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  9. ^ a b Roth BL, Craigo SC, Choudhary MS; et al. (1994). "Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors". The Journal of Pharmacology and Experimental Therapeutics. 268 (3): 1403–10. PMID 7908055. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  10. ^ a b c d e Richelson E, Nelson A (1984). "Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro". The Journal of Pharmacology and Experimental Therapeutics. 230 (1): 94–102. PMID 6086881. {{cite journal}}: Unknown parameter |month= ignored (help)
  11. ^ a b Burstein ES, Ma J, Wong S; et al. (2005). "Intrinsic efficacy of antipsychotics at human D2, D3, and D4 dopamine receptors: identification of the clozapine metabolite N-desmethylclozapine as a D2/D3 partial agonist". The Journal of Pharmacology and Experimental Therapeutics. 315 (3): 1278–87. doi:10.1124/jpet.105.092155. PMID 16135699. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  12. ^ a b c Wei HB, Niu XY (1990). "[Comparison of the affinities of amoxapine and loxapine for various receptors in rat brain and the receptor down-regulation after chronic administration]". Yao Xue Xue Bao = Acta Pharmaceutica Sinica (in Chinese). 25 (12): 881–5. PMID 1966571.
  13. ^ Lim HD, van Rijn RM, Ling P, Bakker RA, Thurmond RL, Leurs R (2005). "Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist". The Journal of Pharmacology and Experimental Therapeutics. 314 (3): 1310–21. doi:10.1124/jpet.105.087965. PMID 15947036. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  14. ^ Midha KK, Hubbard JW, McKay G, Rawson MJ, Hsia D (1999). "The role of metabolites in a bioequivalence study II: amoxapine, 7-hydroxyamoxapine, and 8-hydroxyamoxapine". International Journal of Clinical Pharmacology and Therapeutics. 37 (9): 428–38. PMID 10507241. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)


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