DSM

3-(10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPIN-5-YL)-N-METHYLPROPAN-1-AMINE

Created:	2007-07-17
Last modified:	2020-09-29

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Chemical Details
Formal Charge	0
Atom Count	42
Chiral Atom Count	0
Bond Count	44
Aromatic Bond Count	12

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Chemical Component Summary
Name	3-(10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPIN-5-YL)-N-METHYLPROPAN-1-AMINE
Synonyms	Desipramine; Norpramin
Systematic Name (OpenEye OEToolkits)	3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N-methyl-propan-1-amine
Formula	C₁₈ H₂₂ N₂
Molecular Weight	266.381
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	c1cc3c(cc1)CCc2c(cccc2)N3CCCNC
SMILES	CACTVS	3.341	CNCCCN1c2ccccc2CCc3ccccc13
SMILES	OpenEye OEToolkits	1.5.0	CNCCCN1c2ccccc2CCc3c1cccc3
Canonical SMILES	CACTVS	3.341	CNCCCN1c2ccccc2CCc3ccccc13
Canonical SMILES	OpenEye OEToolkits	1.5.0	CNCCCN1c2ccccc2CCc3c1cccc3
InChI	InChI	1.03	InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3
InChIKey	InChI	1.03	HCYAFALTSJYZDH-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB01151
Name	Desipramine
Groups	approved investigational
Description	Desipramine hydrochloride is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, desipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, desipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as desipramine and nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline and doxepine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H<sub>1</sub> receptors, α<sub>1</sub>-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Desipramine exerts less anticholinergic and sedative side effects compared to tertiary amine TCAs, such as amitriptyline and clomipramine. Desipramine may be used to treat depression, neuropathic pain (unlabeled use), agitation and insomnia (unlabeled use) and attention-deficit hyperactivity disorder (unlabeled use).
Synonyms	Déméthylimipramine Desipramine 5-(gamma-methylaminopropyl)iminodibenzyl Desipramin Desmethylimipramine Désipramine Norimipramine Monodemethylimipramine Desipramine hydrochloride DMI N-(3-methylaminopropyl)iminobibenzyl Desipraminum Desipramina 5-(γ-methylaminopropyl)iminodibenzyl
Brand Names	Desipramine Hydrochloride Ratio-desipramine Tab 10mg Novo-desipramine Sc -tab 75mg PMS Desipramine Hydro Tab 25mg Norpramin 50mg Tab Dom-desipramine Tablets - 50mg Desipramine Desipramine-10 - Tab 10mg Norpramin 25mg Tab Pertofrane Tab 50mg Desipramine HCL PMS Desipramine Hydro Tab 50mg Dom-desipramine Tablets - 25mg Ratio-desipramine Tab 100mg Pertofrane 25mg Penta-desipramine Tablets Desipramine-50 - Tab 50mg Ratio-desipramine Tab 25mg PMS Desipramine Hydro Tab 10mg Ratio-desipramine Tab 50mg Novo-desipramine Fc - 50mg Tab Novo-desipramine Sc - Tab 10mg PMS Desipramine Hydro Tab 75mg PMS-desipramine - Tab 100mg Norpramin 75mg Tab Norpramin 100mg Tab Desipramine-75 - Tab 75mg Novo-desipramine Sc - Tab 25mg Norpramin 10mg Tab Norpramin Tab 50mg PHL-desipramine Norpramin Norpramin Tab 75mg Desipramine-25 - Tab 25mg Ratio-desipramine Tab 75mg Norpramin Tab 25mg
Indication	For relief of symptoms in various depressive syndromes, especially endogenous depression. It has also been used to manage chronic peripheral neuropathic pain, as a second line agent for the management of anxiety disorders (e.g. panic disorder, generalized anxiety disorder), and as a second or third line agent in the ADHD management.
Categories	Adrenergic Agents Adrenergic Uptake Inhibitors Agents producing tachycardia Agents that produce hypertension Agents that reduce seizure threshold Anticholinergic Agents Antidepressive Agents Antidepressive Agents Indicated for Depression Antidepressive Agents, Tricyclic Central Nervous System Agents Central Nervous System Depressants Combined Inhibitors of Serotonin/Norepinephrine Reuptake Cytochrome P-450 CYP2B6 Inhibitors Cytochrome P-450 CYP2B6 Inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2E1 Inhibitors Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) Cytochrome P-450 CYP2E1 Inhibitors (weak) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dibenzazepines Drugs that are Mainly Renally Excreted Enzyme Inhibitors Heterocyclic Compounds, Fused-Ring Histamine Antagonists Histamine H1 Antagonists Membrane Transport Modulators Muscarinic Antagonists Narrow Therapeutic Index Drugs Nervous System Neurotoxic agents Neurotransmitter Agents Neurotransmitter Uptake Inhibitors Non-Selective Monoamine Reuptake Inhibitors OCT1 inhibitors OCT2 Inhibitors P-glycoprotein inhibitors Potential QTc-Prolonging Agents Psychoanaleptics Psychotropic Drugs QTc Prolonging Agents Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome Serotonin 5-HT2 Receptor Antagonists Serotonin 5-HT2A Receptor Antagonists Serotonin Agents Serotonin Modulators Serotonin Receptor Antagonists Tricyclics and Other Norepinephrine-reuptake Inhibitors
ATC-Code	N06AA01
CAS number	50-47-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Sodium-dependent noradrenaline transporter	MLLARMNPQVQPENNGADTGPEQPLRARKTAELLVVKERNGVQCLLAPRD...	unknown	inhibitor
Sodium-dependent serotonin transporter	METTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...	unknown	inhibitor
5-hydroxytryptamine receptor 2A	MDILCEENTSLSSTTNSLMQLNDDTRLYSNDFNSGEANTSDAFNWTVDSE...	unknown	antagonist
Beta-2 adrenergic receptor	MGQPGNGSAFLLAPNGSHAPDHDVTQERDEVWVVGMGIVMSLIVLAIVFG...	unknown	antagonist
Beta-1 adrenergic receptor	MGAGVLVLGASEPGNLSSAAPLPDGAATAARLLVPASPPASLLPPASESP...	unknown	other
Sphingomyelin phosphodiesterase	MPRYGASLRQSCPRSGREQGQDGTAGAPGLLWMGLVLALALALALALSDS...	unknown	inhibitor
Histamine H1 receptor	MSLPNSSCLLEDKMCEGNKTTMASPQLMPLVVVLSTICLVTVGLNLLVLY...	unknown	antagonist
Alpha-1 adrenergic receptors	MVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...	unknown	antagonist
Muscarinic acetylcholine receptor M1	MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISF...	unknown	antagonist
Muscarinic acetylcholine receptor M2	MNNSTNSSNNSLALTSPYKTFEVVFIVLVAGSLSLVTIIGNILVMVSIKV...	unknown	antagonist
Muscarinic acetylcholine receptor M3	MTLHNNSTTSPLFPNISSSWIHSPSDAGLPPGTVTHFGSYNVSRAAGNFS...	unknown	antagonist
Muscarinic acetylcholine receptor M4	MANFTPVNGSSGNQSVRLVTSSSHNRYETVEMVFIATVTGSLSLVTVVGN...	unknown	antagonist
Muscarinic acetylcholine receptor M5	MEGDSYHNATTVNGTPVNHQPLERHRLWEVITIAAVTAVVSLITIVGNVL...	unknown	antagonist
5-hydroxytryptamine receptor 1A	MDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...	unknown	binder
5-hydroxytryptamine receptor 2C	MVNLRNAVHSFLVHLIGLLVWQCDISVSPVAAIVTDIFNTSDGGRFKFPD...	unknown	binder
Dopamine D2 receptor	MDPLNLSWYDDDLERQNWSRPFNGSDGKADRPHYNYYATLLTLLIAVIVF...	unknown	binder
Alpha-2 adrenergic receptors	MGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...	unknown	binder
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	product of
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	inhibitor
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	inhibitor
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	inhibitor
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	inhibitor
Solute carrier family 22 member 3	MPSFDEALQRVGEFGRFQRRVFLLLCLTGVTFAFLFVGVVFLGTQPDHYW...	unknown	inhibitor
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	inhibitor
Solute carrier family 22 member 5	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	inhibitor
Solute carrier family 22 member 4	MRDYDEVIAFLGEWGPFQRLIFFLLSASIIPNGFNGMSVVFLAGTPEHRC...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682