{"ATC Code":"N - Nervous system","Abbreviation":[],"Adverse Effects":"The common adverse effects of amoxapine therapy include, but are not limited to, insomnia, palpitations, tachycardia, hypotension, and constipation. Furthermore, research has indicated that amoxapine may trigger hypomanic states in individuals with underlying bipolar disorder. Amoxapine has been observed to induce noradrenaline-mediated contraction of the urethra in guinea pigs and rats in various laboratory studies, leading to elevated urethral resistance. In addition, the drug has been associated with instances of painful ejaculations relieved by the administration of tamsulosin. Notably, tricyclic antidepressants (TCAs), including amoxapine, are correlated with an increased risk of seizures, especially in older patients and those with epilepsy. Therefore, it is recommended to use SSRIs or SNRIs in patients with a history of epilepsy and seizures.","Aliases":["Asendin","Demolox","Amoxan","Desmethylloxapin","Amoxapina","Asendis","Amoxapinum","Dibenz[b,f][1,4]oxazepine, 2-chloro-11-(1-piperazinyl)-","CL 67772","CL-67772","2-Chloro-11-(1-piperazinyl)dibenz(b,f)(1,4)oxazepine","CL-67,772","CL 67,772","Desmethylloxapine","DIBENZ(b,f)(1,4)OXAZEPINE, 2-CHLORO-11-(1-PIPERAZINYL)-","2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine","Defanyl","2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine","13-chloro-10-(piperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaene","8-chloro-6-piperazin-1-ylbenzo(b)(1,5)benzoxazepine","8-chloro-6-piperazin-1-ylbenzo[b][1,5]benzoxazepine","2-Chloro-11-(piperazin-1-yl)dibenzo(b,f)(1,4)oxazepine","13-chloro-10-(piperazin-1-yl)-2-oxa-9-azatricyclo(9.4.0.0^(3,8))pentadeca-1(11),3(8),4,6,9,12,14-heptaene","CL67,772","N06AA17"],"Biological Half-Life":"8 hours","CAS":"14028-44-5","ChEBI":"CHEBI:2675","ChEMBL":"CHEMBL1113","ChemicalClasses":["benzylpiperazine"],"Chirality":"achiral","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Antidepressive Agents; Serotonin Uptake Inhibitors","Drug Indication":"For the relief of symptoms of depression in patients with neurotic or reactive depressive disorders as well as endogenous and psychotic depressions. May also be used to treat depression accompanied by anxiety or agitation.","EINECS":"237-867-1","Erowid Experience Reports":null,"Esters":[],"European Community (EC) Number":"237-867-1","FDA Pharmacological Classification":"R63VQ857OT","Formating":[],"HMDB ID":"HMDB0014683","HeavyAtomCount":22,"Human Drugs":"Antidepressants -\u003e Tricyclic antidepressants (TCA)","IUPACName":"8-chloro-6-piperazin-1-ylbenzo[b][1,4]benzoxazepine","Impurities":["3-chloro-11-(piperazin-1-yl)dibenzo(b,f)(1,4)oxazepine","n-nitroso-amoxapine","1,4-bis(2-chlorodibenzo(b,f)(1,4)oxazepine-11-yl)piperazine","2-chlorodibenzo(b,f)-1,4-oxazepin-11-one","n-(2-(4-chlorophenoxy)phenyl)piperazine-1-carboxamide","2-(4-chlorophenoxy)aniline","n-carbamoyl amoxapine","chlorophenoxyaniline carbamate"],"InChI":"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","InChIKey":"QWGDMFLQWFTERH-UHFFFAOYSA-N","LD50":[{"dosages":[{"amount":"313 mg/kg","route":"oral"},{"amount":"201 mg/kg","route":"intraperitoneal"},{"amount":"\u0026gt;4500 mg/kg","route":"subcutaneous"}],"organism":"Rat"},{"dosages":[{"amount":"104 mg/kg","route":"oral"},{"amount":"385 mg/kg","route":"subcutaneous"},{"amount":"112 mg/kg","route":"intraperitoneal"}],"organism":"Mouse"}],"LDLo":[{"dosages":[{"amount":"40 mg/kg","route":"oral"},{"amount":"40 mg/kg","route":"oral"},{"amount":"75953 μg/kg","route":"oral"}],"organism":"Human - female"},{"dosages":[{"amount":"20 mg/kg","route":"intraperitoneal"}],"organism":"Dog"},{"dosages":[{"amount":"25 mg/kg","route":"oral"}],"organism":"Human - child"}],"MeSH Pharmacological Classification":"Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system.","Melting Point":"175-176","MolecularFormula":"C\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eClN\u003csub\u003e3\u003c/sub\u003eO","MolecularWeight":"313.8 g/mol","Pharmacodynamics":"Amoxapine is a tricyclic antidepressant of the dibenzoxazepine class, chemically distinct from the dibenzodiazepines, dibenzocycloheptenes, and dibenzoxepines. It has a mild sedative component to its action. The mechanism of its clinical action in man is not well understood. In animals, amoxapine reduced the uptake of nor-epinephirine and serotonin and blocked the response of dopamine receptors to dopamine. Amoxapine is not a monoamine oxidase inhibitor. Clinical studies have demonstrated that amoxapine has a more rapid onset of action than either amitriptyline or imipramine","Physical Description":"Solid","PubChemId":2170,"Record Description":["LiverTox|CNS|Antidepressant|Tetracyclic"],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Amoxapine","Name":"Amoxapine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00543","Name":"Amoxapine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/2170","Name":"Amoxapine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1113","Name":"Amoxapine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2675","Name":"Amoxapine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=14028-44-5","Name":"Amoxapine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014683","Name":"Amoxapine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D00228","Name":"Amoxapine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/R63VQ857OT","Name":"Amoxapine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID7022598","Name":"Amoxapine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 2170, Amoxapine. Accessed August 14, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/2170\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/2170\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Amoxapine. UNII: R63VQ857OT. Global Substance Registration System. Accessed August 14, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/R63VQ857OT\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/R63VQ857OT\u003c/a\u003e"],"SMILES":"C1CN(CCN1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl","SaltData":[],"Salts":[],"Solubility":"34.4 [ug/mL] (The mean of the results at pH 7.4)","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 104.693 77.456\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h105v78H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m84.683 76.418-13.198-7.62M71.485 68.798l.003-11.399M74.643 51.728l10.05-5.807M84.693 45.921l13.198 7.62M97.891 53.541l-.004 11.399M84.683 76.418l10.05-5.807M68.336 51.729l-10.045-5.8\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m48.811 52.418 9.48-6.489M47.434 50.406l8.516-5.829\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m48.811 52.418 4.74-3.244M47.434 50.406l4.258-2.914\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"M42.434 53.545 31.12 50.122\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m21.655 62.017 9.465-11.895M20.623 59.399l7.716-9.698\"/\u003e\u003c/g\u003e\u003cpath d=\"M21.655 62.017 6.579 59.778\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m1.052 45.586 5.527 14.192M3.833 46.007l4.505 11.567\"/\u003e\u003c/g\u003e\u003cpath d=\"m1.052 45.586 9.464-11.896\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m25.592 35.93-15.076-2.24M23.834 38.134l-12.285-1.825\"/\u003e\u003c/g\u003e\u003cpath d=\"M31.12 50.122 25.592 35.93M25.592 35.93l5.625-9.782M36.824 22.177l11.406-1.741\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m48.23 20.436 11.228 10.29M50.921 19.594l9.151 8.387\"/\u003e\u003c/g\u003e\u003cpath d=\"m58.291 45.929 1.167-15.203M59.458 30.726l14.515-4.517\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m73.973 26.209 3.369-14.865M71.906 24.298l2.745-12.112\"/\u003e\u003c/g\u003e\u003cpath d=\"M77.342 11.344 66.113 1.055\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M66.113 1.055 51.599 5.572M65.499 3.799 53.666 7.482\"/\u003e\u003c/g\u003e\u003cpath d=\"m48.23 20.436 3.369-14.864M77.342 11.344 88.7 7.793\" class=\"bond\"/\u003e\u003cpath stroke=\"none\" d=\"M73.43 55.999h-.72l-2.619-4.066h-.03l.03.595q.023.358.023.733v2.738h-.565V51.1h.714l2.608 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482V51.1h.577z\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M99.827 71.239h-.721l-2.619-4.066h-.03l.03.595q.024.358.024.733v2.738h-.566V66.34h.715l2.607 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482V66.34h.578zM104.133 71.239h-.619v-2.286h-2.512v2.286h-.614V66.34h.614v2.071h2.512V66.34h.619z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"none\" d=\"M47.656 56.987h-.721l-2.619-4.066h-.03l.03.595q.024.357.024.733v2.738h-.566v-4.899h.715l2.607 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.768h.578z\" class=\"atom\"/\u003e\u003cpath fill=\"#ff0d0d\" stroke=\"none\" d=\"M35.44 22.73q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.244.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881t1.274-.316q.732 0 1.232.316.5.309.756.875.256.565.256 1.327m-3.863 0q0 .923.386 1.459.393.53 1.221.53.839 0 1.22-.53.387-.536.387-1.459 0-.928-.387-1.452-.381-.524-1.208-.524-.834 0-1.227.524-.392.524-.392 1.452\" class=\"atom\"/\u003e\u003cpath fill=\"#1ff01f\" stroke=\"none\" d=\"M92.382 4.82q-.786 0-1.238.53-.453.524-.453 1.446 0 .911.417 1.447.422.53 1.268.53.321 0 .607-.054.292-.059.566-.143v.536q-.274.101-.566.149-.292.053-.696.053-.745 0-1.251-.309-.5-.31-.75-.875-.25-.572-.25-1.34 0-.744.268-1.309.274-.566.804-.881.53-.322 1.28-.322.78 0 1.351.286l-.244.524q-.226-.101-.506-.185-.274-.083-.607-.083m2.756 4.423h-.601V4.028h.601z\" class=\"atom\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m71.488 57.399-.001 5.7M74.643 51.728l5.025-2.903M97.887 64.94l.002-5.7M94.733 70.611l-5.025 2.903M68.336 51.729l-5.023-2.9M42.434 53.545l-5.657-1.711\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m31.217 26.148-2.813 4.891M36.824 22.177l5.703-.871\" class=\"hi\"/\u003e\u003cpath stroke=\"#1ff01f\" d=\"m88.7 7.793-5.679 1.776\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","TDLo":[{"dosages":[{"amount":"70 mg/kg/3W-I","route":"oral"},{"amount":"4286 μg/kg","route":"oral"},{"amount":"14 mg/kg","route":"oral"},{"amount":"27 mg/kg","route":"oral"},{"amount":"4285 μg/kg/2D-","route":"oral"}],"organism":"Human - male"},{"dosages":[{"amount":"10 mg/kg","route":"oral"}],"organism":"Human - child"},{"dosages":[{"amount":"5 mg/kg","route":"oral"},{"amount":"17 mg/kg","route":"oral"},{"amount":"15 mg/kg/5D-I","route":"oral"},{"amount":"30 mg/kg","route":"oral"},{"amount":"50 mg/kg","route":"oral"}],"organism":"Human - female"}],"Title":"Amoxapine","Treatment":"Treatment of amoxapine overdosage should be symptomatic and supportive, but with special attention to prevention or control of seizures. If the patient is conscious, induced emesis followed by gastric lavage with appropriate precautions to prevent pulmonary aspiration should be accomplished as soon as possible. Following lavage, activated charcoal may be administered to reduce absorption, and repeated administrations may facilitate drug elimination. An adequate airway  should be established in comatose patients and assisted ventilation instituted if necessary. Seizures may respond to standard anticonvulsant therapy such as intravenous diazepam and/or phenytoin. The value of physostigmine appears less certain. Status epilepticus, should it develop, requires vigorous treatment. (L1712)","UNII":"R63VQ857OT","Wikipedia":"Amoxapine","XLogP":2.6}